Sarasota Vacation Rentals

(100 rentals)
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Sarasota Condo
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 1 Bathroom
1 review

Distance to beach: 4 miles to Siesta Key Beach

$193

avg/night

$193
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to your oasis of comfort and style in the heart of Siesta Key, just moments away from the world-renowned Siesta Key Beach and the vibrant city of Sarasota. This meticulously designed 2-bedroom condo offers a perfect blend of modern elegance and coastal charm. Escape the crowds and enjoy the serenity ...

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Property Type

Sarasota Condo

Featured review

"Convenient location to beach, shopping and attractions"

The condo was conveniently located close to Siesta Key and other beautiful beaches. The condo was within walking distance to shopping, restaurants and other attractions. The fenced in backyard and walking ...

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Sarasota Villa
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms
9 reviews

Distance to beach: 2 miles to Siesta Key and Turtle

$147

avg/night

$147
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

Quiet, private and pet friendly 2 bedroom, 2 bath, in Gulf Gate just 4 minutes to Siesta Key and her Beaches! All Florida (12% state & bedding) taxes are 'included' in rental the fee. THERE ARE NO OWNERS FEE OR SERVICE FEES. Be Our Guest...very quiet, clean and comfortable non-smoking ...

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Property Type

Sarasota Villa

Featured review

"Nice place in a comfy neighborhood"

We appreciated the chance to try a new Snowbird spot this year. Amy’s place is convenient to some shops and a modern library nearby. Also great to have the paved Legacy Trail and mellow Gulf Gate streets ...

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$133

avg/night

$133
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

SEASONAL RENTAL 4 MONTH MINIMUM AVAILABLE NOVEMBER 1 THROUGH APRIL 30 ***Pay in full discount*** $150.00 fee for background check(tenant pays) The owner will not be in Florida until October 11 for showings if required. Welcome to Summerwind, a peaceful oasis close to downtown Sarasota. ...

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Property Type

Sarasota Condo

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Sarasota Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
3 reviews

Distance to beach: 2 miles to Lido

$207

avg/night

$207
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Relax at this lovely comfortable and spacious one bedroom or studio apartments with gorgeous new inground swimming pool at the Southside Village Resort. Check out our website for all the various options that are available. We are located in the wonderful Southside Village, also known as the Hillview ...

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Property Type

Sarasota Apartment

Featured review

"2 week holiday"

Fantastic. Like home away from home. great Hosts and beautifully located. Flat was sparkling clean and jason and Dee and their son Storm always on hand for any help required. We can only highly reccomend ...

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Sarasota House | On the beach
3 BR | 3.5 BA | Sleeps 7 | Quick View
Sleeps 7, 3 Bedrooms, 3.5 Bathrooms
3 reviews

$375

avg/night

$375
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

Our 3 bedroom, 3 1/2 bath beach house is located on Siesta Key and is on the gulf side of Beach Road. Our home is a standalone unit on 3 levels with 2 decks, a ground level patio, with a on e car garage. We are directly on Crescent Beach with gulf views and have a private access to the beach. It is ...

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Property Type

Sarasota House

Featured review

"Well taken care of beach front rental."

This house was great for our family. It was right on the beach and walking distance to town. It was clean and I don’t think we saw a bug inside the whole time. Great communication with the owner as well. ...

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Sarasota House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

updated 10/14: Fortunate to have no hurricane damage. 3 bedroom/2 bath home located near the south bridge to Siesta Key. Bright and airy beach style decor. Light filled open format living room, dining room, kitchen. 65" flat screen smart TV with Hulu-live TV Master Suite with king bed, ...

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Property Type

Sarasota House

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Sarasota House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2.5 Bathrooms
3 reviews

$305

avg/night

$305
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

This has just become available for winter of 24-25. The renter for the past 13 years has bought a place of their own nearby. The house is a bright, newer construction (in 2011) 3 bedroom home near the Siesta Beaches. This property is nestled in a quiet community a 10 minute walk from the white sands ...

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Property Type

Sarasota House

Featured review

"Comfortable home in a great neighborhood"

We’ve been renting 6217 Beechwood from Bill for many years. Once we found this house and neighborhood, we knew we had found the perfect place for our Florida visits! The house is large and well designed. ...

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Sarasota House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
3 reviews

Distance to beach: 5 miles to Siesta Key

$285

avg/night

$285
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Charming old Florida home in a cul-de-sac backing to large palm and oak trees. Three bedrooms, two full baths. One outside shower. Quiet and quaint street. Freshley painted and new carpet through-out. All new beds and furniture. Two king bedrooms with dressers and smart TV's, wi-fi in place. One ...

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Property Type

Sarasota House

Featured review

"Relax and recharge at Turtle Cove!"

Immaculate and spacious home with private pool, screened lanai, and modern applicances. Located in a quiet, centrally located Sarasota neighborhood within a short drive to great restaurants, Siesta Key, ...

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Sarasota House
3 BR | 2.5 BA | Sleeps 12 | Quick View
Sleeps 12, 3 Bedrooms, 2.5 Bathrooms

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Very nice & Spacious 3 bedms/2.5bathms home with heated swimming-pool in Euclid Ave. Near beaches (15min) and downtown (5min) and Shopping St Armand Cir (15 min). Perfect for family and friends. Modern comfort renovated with a large garden Near to Yoder's Fresh market and Arlington park (playing ...

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Property Type

Sarasota House

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Sarasota Townhome
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2.5 Bathrooms
2 reviews

Distance to beach: 11 miles to Siesta Key Beach

$193

avg/night

$193
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Step inside this beautiful townhome and discover a thoughtfully designed space that exudes comfort and style. The townhome boasts modern features, including fixtures and appliances ensuring both functionality and elegance. Located just a short drive (~20 minutes) to Siesta Key Beach, rated the #1 ...

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Property Type

Sarasota Townhome

Featured review

"New, Comfortable Townhouse"

We had a very relaxing stay at this brand new, super clean, comfortable townhouse. Our host was so understanding to help accommodate my husband and I at the last minute! Since this was a new rental, there ...

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Sarasota Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 Bedroom, 1 Bathroom
1 review

$216

avg/night

$216
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Keep it simple at this centrally-located, pet friendly, turn-key including an espresso machine! This 1 bedroom queen/ 1 ba apartment is catty corner to 10 acre Gillespie park w/2 dog parks, tennis courts, pickle-ball, basketball, & walking trails. Minutes to the #1 beaches & shopping at St. Armand’s ...

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Property Type

Sarasota Apartment

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Sarasota House
3 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 3 Bedrooms, 3 Bathrooms
5 reviews

$315

avg/night

$315
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Enjoy being close to everything at this smoke free centrally-located, peaceful catty-corner to Sarasota’s 10 acre Gillespie Park home. Minutes to the beaches, & walk to shopping, restaurants, bay front, arts, Whole Foods, coffee shops, etc. This 3 BD/3.5 BA home includes a detached over-sized ...

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Property Type

Sarasota House

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
4 reviews

Distance to beach: 0.5 miles to Siesta Key Crescent Beach

$283

avg/night

$283
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

NEWLY REMODELED - LUXURY WATERFRONT CONDO FOR COUPLES GETAWAY - BOAT DOCK/PRIVATE SLIP FOR BOAT/JET SKIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment. Sit on the lanai and watch the boats, dolphins, manatees, pelicans and other wildlife - it is a gorgeous spot! Walk ...

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Property Type

Sarasota Condo

Featured review

"Incredible stay!! 10 stars out of 5."

Beautifully decorated condo in prime location. Extra clean and upscale. Best location on the harbor with water views and walking distance across the bridge onto Siesta Key's Tiki Bar. Owner is a pleasure ...

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Sarasota Condo
2 BR | 2 BA | Sleeps 3 | Quick View
Sleeps 3, 2 Bedrooms, 2 Bathrooms
5 reviews

Distance to beach: 14 miles to Siesta Key Beach

$183

avg/night

$183
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Our penthouse condo is located in Sarasota (Manatee County), Florida within the Palm Aire residential condominium community at Palm Aire at DeSoto Lakes, Inc., Golf Side. It is uniquely situated on the top floor of the only 4-story building erected within the Golf Side community. Directly across from ...

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Property Type

Sarasota Condo

Featured review

"Relaxing established neighborhood"

Condo was very comfortable for 2 people. If you don’t mind a queen size bed. Great view of golf course off back glassed in sitting area. Though this unit doesn't come with golf privileges. It is very ...

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Sarasota House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$171

avg/night

$171
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Arlington Hurricane Block Home with 2 Bedroom, 2 Bath home with "extra room" for sleeping, office, movie watching, etc. Remodeled bathrooms, bedrooms, new air conditioner, water heater, washer/dryer, vinyl plank waterproof flooring throughout. Owner uses this home as well.

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Property Type

Sarasota House

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Sarasota House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2.5 Bathrooms
7 reviews

Distance to beach: 3 miles to Siesta Key

$431

avg/night

$431
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

**HURRICANE UPDATE** All tree limb debris has been cleared and the property is as beautiful as ever. So please, book and stay with confidence! Welcome to Magnolia House Sarasota, a meticulously appointed, “swim and soak” retreat featuring a heated pool and spa/hot tub in a lush Areca palm-landscaped ...

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Property Type

Sarasota House

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Sarasota Condo | On the beach
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3.5 Bathrooms

$1215

avg/night

$1,215
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Immerse yourself in beachfront bliss at Lido Bliss: Imagine stepping off the elevator into your private sanctuary. Breathtaking panoramic views of the Gulf of Mexico greet you from your expansive balcony, setting the scene for an unforgettable stay. This meticulously kept, 4-bedroom 3.5 bath haven exudes ...

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Property Type

Sarasota Condo

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Sarasota House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
3 reviews

$294

avg/night

$294
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

The house is a bright, open floor plan, 3 bedroom, 2 bath home near the Siesta Beaches. Within a 15 minute drive are numerous golf courses, Benderson rowing facility, many very good locally run restaurants of diverse ethnicities, and large shopping malls. This property is nestled in a quiet community ...

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Property Type

Sarasota House

Featured review

"Awesome Place!"

We escaped here from the cold northeast and it was perfect! Fully stocked kitchen that made it so easy to cook and pretend it's our own house. Super close to the beaches without having to deal with the ...

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Sarasota Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

Distance to beach: 50 yards to Lido Beach

$283

avg/night

$283
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

HURRICANE UPDATE, October 29, 2024 Having a condo on the ground floor directly on the beach is always a fantastic thing. But this year with hurricanes Helene and Milton, its been a challenge. Hurricane Helene storm surge caused 3 inches of water to enter our unit. In addition, Milton tore up the ...

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Property Type

Sarasota Condo

Featured review

"Absolutely Wonderful"

We rented this gorgeous Condo for the month of March, 2024. First of all, the location is perfect, right on Lido Beach with a pool onsite and right down the street from St. Armand's Circle in Sarasota. ...

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Sarasota Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
1 review

$325

avg/night

$325
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Lido Key is the ultimate spot for your tropical vacation. This amazing condo is in a gated community at the Southern end of Lido Key. Just steps outside the door you will be on the luxurious sugar sand beach with spectacular views of multiple islands on the Gulf. On the property you will also find a private ...

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Property Type

Sarasota Condo

Featured review

"A little piece of paradise"

First time being snowbirds and we couldn’t have picked a nicer place. Situated right on Lido Key Beach. The condo was great and had everything we needed. Walked out the back door and we were just steps ...

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Sarasota House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 2 Bathrooms
13 reviews

$385

avg/night

$385
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

ONLY 2 MILES TO IMG ACADEMY. PREFECT! Experience the allure of this stunning 4-bedroom, 2-bath home. Impeccably updated with style, it boasts an inviting open floor plan. Delight in the free heated pool and indulge in vacation amenities! Nestled along Bowles Creek, you can fish, unwind, or feed friendly ...

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Property Type

Sarasota House

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Sarasota Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom

$167

avg/night

$167
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Keep it simple at this smoke free centrally-located, pet friendly, turn-key including an espresso machine! This 1 bedroom queen/ 1 ba apartment is catty corner to 10 acre Gillespie park w/2 dog parks, tennis courts, pickle-ball, basketball, & walking trails. Minutes to the #1 beaches & shopping ...

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Property Type

Sarasota Apartment

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$241

avg/night

$241
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

A Great Home Away from Home Boatyard Gated Community Comfy Lanai for relaxing and entertaining Bamboo Wood Floors 2 bedrooms (one king and one queen bed) and 2 bathrooms Heated Pool Upgraded features include new paint and wonderful main bedroom walk in shower Wonderful fishing with several ...

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Property Type

Sarasota Condo

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
1 review

Distance to beach: 0.5 miles to Siesta Key

$288

avg/night

$288
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

NEWLY DECORATED LUXURY WATERFRONT CONDO FOR COUPLES GETAWAY - BOAT DOCK /PRIVATE SLIP FOR BOAT(When Available)/JET SKIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment. Sit on the lanai and watch the boats, occasional dolphins & manatees, pelicans and other wildlife ...

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Property Type

Sarasota Condo

Featured review

"Comfortable Condo"

This is such a comfortable, well decorated and fully equipped condo. The location was very quiet with nice views and in a great location for accessing the beach and siesta key. You can easily bike to siesta ...

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Sarasota House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Turnkey furnished home, 3 bedrooms, 2 bathrooms, 2 car garage, king bed in master bedroom with walk-in shower, soaking tub and large walk-in closet. Queen beds in the 2 guest rooms. Heated private pool.

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Property Type

Sarasota House

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Sarasota Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
3 reviews

Distance to beach: 3 miles to Siesta Key

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Newly renovated 1br/1ba, 2nd floor condo in the Sienna Park, Sarasota, Fl. A community pool and a tennis court are provided at 1+1 condo, which is set in Sarasota, 5 min drive from Siesta Key Public Beach. This apartment offers air-conditioned accommodation with a balcony. The apartment features 1 separate ...

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Property Type

Sarasota Condo

Featured review

"Awesome place to stay"

We were in unit 146 and totally loved it. So clean and welcoming. Would definately rent again. Thank you!

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Sarasota Studio
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 Bedrooms, 1 Bathroom
1 review

Distance to beach: 2 miles to Crescent Beach

$74

avg/night

$74
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Year-End Special: Nov-Dec for $1850/month, all-in. Extra Multi-month discounts available! No hidden fees. Discount available if booking more than 1 month. Beautiful comfortable Studio fully furnished with washer/dryer in the unit. Located in a quiet street in the popular Gulf Gate neighborhood , ...

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Property Type

Sarasota Studio

Featured review

"Spacious and Charming !!!!"

Maite's place is really clean ,spacious and convenient everywhere .The studio is well taken care of .Maite promptly responded to any request .We enjoy our stay during our time in Siesta Key !!!

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Sarasota House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2 Bathrooms

$199

avg/night

$199
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Welcome to 3180 Dividing Creek, a stunning rental property located in the beautiful city of Sarasota, Florida. This spacious home offers an ideal blend of comfort, style, and convenience, making it the perfect choice for your next getaway. Featuring 4 bedrooms and 2 bathrooms, this property provides ...

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Property Type

Sarasota House

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Sarasota Cottage
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 Bedrooms, 1 Bathroom
32 reviews

Distance to beach: 0.5 miles to 10 minute walk

$97

avg/night

$97
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

F & F represents "Friends & Family" and we work hard in these times to make a retreat to go to which we all need that. This property is our year-round Homestead property. Somethings like privacy you won't find anywhere else. Many years we have been using Cleaning Product Mixtures ...

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Property Type

Sarasota Cottage

Featured review

"Very nice cottage"

Our host Cynthia has thought of everything anyone could need. Excellent location. We booked for next year

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Sarasota House
8 BR | 8 BA | Sleeps 20 | Quick View
Sleeps 20, 8 Bedrooms, 8 Bathrooms

$1877

avg/night

$1,877
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Gillespie Park includes 10 acres of trails, playground, basketball, pickleball courts, tennis courts, pond & 2 public dog parks and is just a 7-10 minute drive to Lido Key Beach & International renowned St. Armands Circle. Come home to this charming and spacious compound with a total of 8 ...

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Property Type

Sarasota House

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
owner special
Owner special: Enjoy 15% off December!

Distance to beach: 0.5 miles to Siesta Key Crescent Beach Access 12

$283

avg/night

$283
avg per night
Owner special:
Enjoy 15% off December!

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

This newly decorated luxury condominium is located in The Boatyard, a highly sought after, gated community on the intracoastal. It is within walking distance to gorgeous Siesta Key Crescent Beach, many water sport activities, shopping, restaurants and more. Private boat slips are also available, right ...

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Property Type

Sarasota Condo

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$259

avg/night

$259
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to your fully furnished, Downtown Mid-Century Modern-meets-Art Deco Masterpiece, in historic Gulfstream Towers! Located both directly across from the Marina, and right off Main Street, this Turn-Key gem is footsteps from all the best dining and shopping options downtown. Designed with a bright ...

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Property Type

Sarasota Condo

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Sarasota House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms
10 reviews

$469

avg/night

$469
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Enjoy being close to everything at this smoke-free, centrally-located, peaceful catty-corner to Sarasota’s 10 acre Gillespie Park home. Minutes to the beaches, & walk to shopping, restaurants, bay front, arts, Whole Foods, coffee shops, etc. This 3 BD/3.5 BA home includes a detached over-sized ...

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Property Type

Sarasota House

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Sarasota House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Ocean Sky, a luxurious retreat that offers the perfect combination of comfort, convenience, and style. From the moment you step inside, you'll be greeted by a meticulously designed interior that caters to your every need. Ocean Sky features three spacious bedrooms and two full baths, ...

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Property Type

Sarasota House

Featured review

"Wonderful house"

A beautiful home with everything that you can possibly need. The pool was outstanding since the temps were 90 degrees plus! The communication with the office was fantastic. Everything was provided for ...

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Sarasota House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 3 Bathrooms
3 reviews

$460

avg/night

$460
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Casamigos, a rare upscale jewel in a sea of vacation rentals. This beautiful, newly furnished 4 Bedroom (all King Beds) /3BA home offers an exceptional vacation experience for your family and friends. It begins with lavish tropical landscaping (Malaysian and Areca Palms, Bougainvillea) and ...

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Property Type

Sarasota House

Featured review

"Highly recommend this host"

Beautiful home. It was spotless when we arrived. All the beds and pillows were extremely comfortable. The Host was very accommodating to all our needs all week. Outside pool and Tiki Bar were a big hit ...

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Sarasota House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms

$264

avg/night

$264
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Located in a quiet cul-de-sac, this property offers a peaceful and tranquil setting. Away from the hustle and bustle of the city, you can enjoy a serene and calm environment in your own home. The private lanai with a saltwater pool provides a secluded outdoor space where you can relax and unwind. Whether ...

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Property Type

Sarasota House

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Sarasota Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms
8 reviews

$480

avg/night

$480
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

Crystal Sands, Siesta Key, Sarasota April price drop for Last minute deal - $2500 Amazing Views!! Our property is right on the beach. Take the elevator down and you're at the ocean. The views are amazing as you can see in the pics. Sit on the lanai for breakfast and watch the activities on the ...

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Property Type

Sarasota Condo

Featured review

"AMAZING 2-Weeks!!!!!"

We loved every minute of our 2-week stay at Crystal Sands, the unit was beautiful and views breathtaking. We were a stones throw from the beach and it couldn't have been any better. I highly recommend!

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
1 review

$325

avg/night

$325
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Situated on the Sarasota Intercoastal Waterway just South of the Stickney Point Bridge on the mainland, our 2 bedroom, 2 bathroom with Bonus room awaits you! Park your boat right outside your door with the 36 ft. boat slip that comes with this property! Conveniently located within walking distance ...

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Property Type

Sarasota Condo

Featured review

"Siesta Beauty!"

The location is amazing, the condo is beautiful and the owner is awesome. The beach is a short 10 min walk, as well as numerous restaurants/bars and coastal shops. There are a couple of different free ...

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Sarasota Villa
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

Distance to beach: 3 miles to Lido Beach

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

This is a 2 bedroom 2 bath villa. Single story. 2 assigned parking spaces. Heated pool. Small quiet complex near downtown. Fully furnished with 2 queen sized beds and a queen pull out couch. There is a lanai with table and chairs. BBQ grill out back. Beach chairs and umbrella included. Two blocks to Fruitville ...

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Property Type

Sarasota Villa

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Sarasota Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
4 reviews
last minute deal
LAST MINUTE DEAL 12/1 - 12/10: Last minute available winter retreat in Sarasota, walking distance to shops, restaurants and bay

Distance to beach: 2 miles to Siesta Key beach

$140

avg/night

$140
avg per night
Offer for: Dec 1 - Dec 10:
Last minute available winter retreat in Sarasota, walking distance to shops, restaurants and bay

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

OUR RATES: January $3900 February- March $4500 April $3000 *Calendar months only. *Pet Friendly, Private Yard, First Floor Unit. *Community pool and gym in Complex. *Ask for our 6-month plus special rate *Boutique-style condominium community ...

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Property Type

Sarasota Condo

Featured review

"Oasis on Osprey unit 107A"

Location,location...This condo was perfectly located for easy access to Siesta Key and downtown Sarasota as well as convenient walkable areas.All information and photos were exactly as described in the ...

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DEAL
Sarasota House | On the beach
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 Bedrooms, 3 Bathrooms

$600

avg/night

$600
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

Are you searching for the perfect vacation home in Siesta Key? Your search ends here! This luxurious property boasts 3 bedrooms, 3.5 bathrooms, and breathtaking ocean views from multiple balconies. Enjoy some relaxation time in the enclosed spa located in the fenced backyard, or take advantage of the ...

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Property Type

Sarasota House

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
3 reviews
last minute deal
LAST MINUTE DEAL 12/1 - 12/10: Last minute available winter retreat in Sarasota walking distance to shops, restaurants and bay!

Distance to beach: 1 miles to Siesta Key

$112

avg/night

$112
avg per night
Offer for: Dec 1 - Dec 10:
Last minute available winter retreat in Sarasota walking distance to shops, restaurants and bay!

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

OUR RATES: December 2024 $2500 January 2025 $4600 February-March 2025 $5200 April 2025 $3900 *Calendar months only. *Ask for our 6-month plus special rate *Pet Friendly, Community pool and gym,boutique-style condominium ...

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Property Type

Sarasota Condo

Featured review

"A Year to Enjoy"

I have had the opportunity to stay at The condos here on S.Osprey Ave in 1 bedroom and 2 bedroom condos, both were wonderful!! . For a year I was able to stay in condo 102A it is a two bedroom two bath ...

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DEAL
Sarasota Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
16 reviews

Distance to beach: 4 miles to Nokomis, Turtle Beach, Siesta Key, Venice etc.

$102

avg/night

$102
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

NOTE, SPECIAL LOW RATE FOR NOV 2024 WHICH IS AVAILABLE. Very pleasant tastefully furnished condo at this attractive and friendly golf and country club community. Ideal vacation spot. Lovely morning sun at east lanai and afternoon sun at west lanai overlooking 18th tee and pond. Master bedroom with ...

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Property Type

Sarasota Condo

Featured review

"Very nice"

Nice, comfortable, well furnished condo in a very good location. Short drive to several beaches. Nice amenities and very close to pool. Very nice golf course and a screened in lanai to overlook a lake ...

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Sarasota House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
14 reviews
owner special
Owner special: SALE..DECEMBER month $2900 or 3 weeks $2100 or 2 weeks $1500. All taxes included, Pet Friendly!

Distance to beach: 2 miles to Siesta Key Beach / Cresant Beach

$114

avg/night

$114
avg per night
Owner special:
SALE..DECEMBER month $2900 or 3 weeks $2100 or 2 weeks $1500. All taxes included, Pet Friendly!

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Quiet, private and pet friendly 2 bedroom, 2 bath, swimming pool home in Gulf Gate just 5 minutes to Siesta Key and her Beaches! Your Rental Fee includes the following (Rent, Cleaning Fee, Florida 12% taxes, Cable, Water & Utilities). Pet Fee additional to rental fee. NO Owners or Service Fees, ...

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Property Type

Sarasota House

Featured review

"Amazing!"

Great clean place! Perfect! Pet friendly! Have everything! Beautiful yard and pool! Great communication

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Sarasota House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 Bedrooms, 4.5 Bathrooms
3 reviews

$1175

avg/night

$1,175
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

This space offers 6 bedrooms (sleeps 16) 2 common areas (sleeps 4 on 2 rollaway beds and 1 double sleeper sofa bed), 4 full bathrooms, and a half bath. The abundance of natural Florida sunshine flows seamlessly throughout the home because of its many windows. Enjoy a sense of peace and tranquility throughout ...

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Property Type

Sarasota House

Featured review

"Fantastic, 5 STARS"

Have rented this home twice in the last 3 months because it is outstanding. Traveled from MD to Sarasota with clients for golf and this is our go to rental. Hot tub, pool, several entertaining spaces ...

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Sarasota Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
3 reviews

$101

avg/night

$101
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

HURRICANE HOUSING NOV. THRU DEC. 31st. AVAILABLE JAN. 1st through April. All winter. Tucked behind Bobby Jones Golf Course you will discover One of Sarasota's Best Kept Secrets! "The Hideaway" Uniquely Designed Villa Overlooking the Golf Course, Pool. Private, Screened Courtyard, ...

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Property Type

Sarasota Condo

Featured review

"Condo"

We actually stayed at a different one from what was listed owner has 9 rental properties. Overall was fine. Outside could use updates.

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Sarasota Apartment
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 1 Bathroom

Distance to beach: 4 miles to Siesta Key Beach

$123

avg/night

$123
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Newly renovated 2br /1 ba, shower cubicle, 980sqft, ground floor, private backyard, condo in the Sienna Park, Sarasota Fl.

View all property information

Property Type

Sarasota Apartment

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Sarasota Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$305

avg/night

$305
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Enjoy Gulf sunsets and the sounds of the surf from your 2nd floor beachfront condo - just one flight of steps - or use the elevator. Unit A205 offers the perfect place to enjoy the sea and sky from sunrise to sunset! On the Gulf side, a spacious lanai offers an unobstructed 180 degree view. Watch as ...

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Property Type

Sarasota Condo

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Sarasota Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
1 review

Distance to beach: 5 miles to Siesta Key Public Beach Access

$123

avg/night

$123
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Come and unwind in this quiet and cozy 2 br/1.5 ba, first floor end unit condo, situated just a short 10 minute drive to the cool emerald waters of Siesta Key, named the nation's best beach - twice! Relax in this tastefully furnished condo located in a small, quiet community, surrounded by grocery ...

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Property Type

Sarasota Condo

Featured review

"Cozy"

We had a wonderful stay in this beautifully decorated and updated condo. Enjoyed the pool. The place was quiet and close to the beach. The owner was very friendly and accommodating. We loved it so much ...

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Sarasota House
2 BR | 3 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 3 Bathrooms
2 reviews

$375

avg/night

$375
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

To view complete details call This home is a beautiful waterfront beach bungalow located on Little Sarasota Bay on the desirable and less congested location of South Siesta Key, Sarasota FL. This sanctuary is within walking distance of the public amenities of Turtle Beach, the Tiki Hut Pub, Bayfront ...

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Property Type

Sarasota House

Featured review

"Perfect getaway!"

This house and grounds were AMAZING! The decks, dock, and gliders were relaxing and quiet-we enjoyed the bird watching and saw dolphins on our last day! Turtle Beach is nice-not quite Siesta Key sand, ...

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Sarasota Vacation Rentals

Sarasota Weather

 | 

7222°  5111°
JANUARY
Ocean 6518°
7423°  5312°
FEBRUARY
Ocean 6518°
7725°  5714°
MARCH
Ocean 6820°
8228°  6016°
APRIL
Ocean 7423°
8731°  6518°
MAY
Ocean 7926°
9032°  7122°
JUNE
Ocean 8328°
9133°  7323°
JULY
Ocean 8529°
9133°  7323°
AUGUST
Ocean 8731°
9032°  7222°
SEPTEMBER
Ocean 8529°
8529°  6518°
OCTOBER
Ocean 8228°
8027°  5915°
NOVEMBER
Ocean 7624°
7423°  5312°
DECEMBER
Ocean 7021°

Sarasota is the “Grand Dame of the Gulf Coast”


Warm temperatures year-round, award-winning beaches, a thriving arts and cultural scene, and amazing Sarasota vacation rentals have made Sarasota a go-to place for couples and families. This southwest Florida area, which is about an hour from Tampa and two hours from Orlando, continues to attract travelers with great restaurants and plenty of shopping. The beauty of Sarasota will get your attention on your first visit. If you see Sarasota first from the window of an airplane, the colors of the Gulf of Mexico and Sarasota Bay, contrasting with the brilliant white sand of Longboat, Lido, and Siesta beaches, will make you anxious to see more.

When staying in one of our Sarasota vacation rentals instead of a traditional hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our Sarasota beach house rentals even come with special amenities like a backyard pool, washer/dryer units, and bicycles. Whether you’re looking for a beach condo with amazing views, or a larger home for space for the entire family, you can find it on our site.

Sarasota, Florida travel advice


Sarasota is growing -- with more attractions, more people, and more infrastructure. Sarasota County has 13 public beaches and over 35 miles of powder-soft sand along the beachfront. Sarasota's Siesta Key Beach has been consistently named one of the top beaches in the United States. Sarasota County also has over 1,000 public, private and semi-private golf courses for residents and visitors to enjoy, so bring your clubs! 

One of Florida’s primary Gulf Coast cities, Sarasota offers visitors an eclectic blend of culture and fine dining, circus thrills and pristine beaches. 

Climate


Sarasota is warm year round. The tropical temps bring about high humidity and afternoon showers. Temps shoot up to the low 90s on the coast in the summer, and passing thunderstorms are just that: passing. Hurricanes may be spotty between July and November. But overall, 300+ sunny days and wonderful weather greets you in Sarasota.

Top activities and attractions in Sarasota


Wealthy notables called Sarasota home in the 19th and 20th centuries, which leads to the nickname the “Grand Dame” of the Gulf Coast. The chic resort town has been home to snowbirds for many, many years.

Shopping starts at St. Armands Circle. Stroll along the streets lined with coconut palms and pop into the 130 upscale shops, restaurants, and specialty stores. In the center of the shopping quadrants you’ll find Circle Park with Italian statues from John Ringling’s personal collection. Another nice walking area is Burns Court Historic District. Listed on the National Register of Historic Places, the area south of downtown Sarasota is made up of 15 stucco bungalows in vibrant hues like cornflower blue and fuchsia. They house everything from art galleries to residences.

The Ringling Museum of Art pays homage to the Ringlings, the family behind America’s most famous circus. Check out the old costumes, wagons, and the world’s largest miniature circus. You can also tour Ca' d'Zan Mansion, a magnificent 56-room Venetian Gothic palace and the Ringlings' old family home. You could spend days covering the 66-acre Ringling campus, but take time to walk the grounds. In particular, swing by Mable Ringling’s Rose Garden, the oldest continuously operating rose garden in the state, and the Museum of Art courtyard, with replicas of ancient Greek, Roman and Baroque statues on a pristinely manicured lawn and lining the top of the buildings.

Nature lovers visiting the area gravitate to the Mote Marine Laboratory & Aquarium in St. Armands Circle, where sea turtles, manatees, and sharks are on display. If you want more nature, check out the Crowley Museum and Nature Center, a 190-acre wildlife sanctuary, and the Marie Selby Botanical Gardens, a lush, 11-acre bay-front setting with more than 20,000 plants.

Art connoisseurs of every kind will discover that the art scene in Sarasota is just as vibrant as it is diverse! Experience world-class opera performances at the Sarasota Opera House, or watch the dancers of the Sarasota Ballet, glide gracefully across the stage. The Asolo Repertory Theatre is Florida’s premier professional theatre and hosts up to 15 different productions each year.

Take a walk on the wild side and see some of nature’s most gorgeous creatures at Big Cat Habitat & Gulf Coast Sanctuary. The adventurer in your family will love the Myakka River State Park for its ample opportunities for boating, fishing, kayaking, and tons of other outdoor activities. 

Annual Events


There’s always something fun happening in Sarasota. The action starts in April during the popular Sarasota Film Festival. Independent filmmakers, actors, and directors converge on the town to showcase 200 hundred films over this ten-day event. Also in April is the Siesta Fiesta in nearby Siesta Key. You can also check out a spring training game for the Baltimore Orioles in April/March. 

Restaurants and Bars


Hungry? Sarasota restaurants have whatever you need. Start with Dolce Italia which is an upscale Italian restaurant that serves some of the best risotto you’ll ever have. End the meal with a sweet, light tiramisu. French fusion spot Antoine’s Restaurant combines French with Belgian cuisine and offers an incredible array of adventurous dishes. If your group is craving seafood, Veronica Fish & Oyster is the spot. If you’re looking for fresh seafood but with a more casual atmosphere, try Duval’s and the shrimp Po Boy. Owen’s Fish Camp has the best fish sandwiches and pecan pie, while the Screaming Goat serves up homestyle favorites like short rib tacos and cheesy tots.

When the sun goes down, the Sarasota nights heat up. Check out the two dozen daiquiri flavors available at the Daiquiri Deck which has one of the most beautiful ocean views in the area. The Beach Club is by far the most popular bar in Sarasota, and you should stop in for one of the themed events they throw. Lastly, located in Downtown Sarasota, Pangea Alchemy Lab isn’t your typical bar or cocktail lounge. This speakeasy tucked inside a sandwich shop is pouring unique libations like boozy cereal and their famous Blue Mule. 

Why you should book a Sarasota vacation rentals by owner on FloridaRentals.com


Booking a Sarasota beach rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!



FAQ

How many vacation rentals are there in/around Sarasota?

There are 100 Sarasota vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Sarasota?

There are vacation rentals available in Sarasota for as low as $74 per night with an average price per night of $236.

Can I find a vacation rental in Sarasota?

Yes, you can find vacation rentals in Sarasota close to The RIngling, Mary Selby Botanical Gardens, and Mote Marine Laboratory. Don't forget to stop in to Myakka River State Park or St. Armand's Circle.

Do any vacation rentals in Sarasota have a pool?

Yes, there are 37 vacation rentals with a pool in Sarasota on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Sarasota vacation rentals on the ocean?

There are 8 oceanfront rentals in Sarasota available on FloridaRentals.com. Use our filters to search and book yours today!