Monthly Rentals in Sarasota

(71 rentals)

Are you looking for a sunny getaway? Our monthly rentals in Sarasota, Florida, offer the perfect escape. Whether you're seeking a winter retreat or a long-term stay, Sarasota has it all. From stunning beaches to vibrant cultural scenes, there’s something for everyone.

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$272

avg/night

$272
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$227

avg/night

$227
avg per night
View Details

Key Amenities

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

About this property

Escape to your own slice of paradise in the heart of Sarasota's coveted Gulf Gate community with this beautifully updated 2-bedroom, 2-bathroom retreat, designed with a relaxing stay in mind. Featuring a heated, caged pool, and just moments away from the world-renowned Siesta Key Beach, this gem ...

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Property Type

Sarasota House

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Sarasota House
3 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 3 bedrooms, 3 bathrooms
7 reviews

$349

avg/night

$349
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • WiFi

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 | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

$249

avg/night

$249
avg per night
View Details

Key Amenities

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

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 Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

Distance to beach: 1 miles to Siesta Key

$226

avg/night

$226
avg per night
View Details

Key Amenities

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

About this property

ONE OF THE BEST LOCATIONS IN SARASOTA! Very nice and quiet condo complex. Three miles close to the most beautiful beach in the United States. All amenities are within walking distance; groceries, restaurants, entertainment, etc! 1 Bedroom condo can comfortably accommodate up to 4 people One queen ...

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Property Type

Sarasota Condo

Featured review

"Pristine golf course and beautiful condo"

We were very pleased with our condo which was very modern and well organized. Views, pools and amenities were to notch.

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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

$330

avg/night

$330
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 Condo | On the beach
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

$1307

avg/night

$1,307
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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 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

$311

avg/night

$311
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom
1 review

Distance to beach: 4 miles to Siesta Key Beach

$116

avg/night

$116
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$229

avg/night

$229
avg per night
View Details

Key Amenities

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

About this property

Amazing 4 bedroom, 2 bathroom house in Sarasota. Amenities included: central air, central heat, deck, dishwasher, hardwood floors, pool, stainless steel appliance, updated bathroom, laundry in building, and yard. No Utilities included. Is pet friendly. $3,200/month rent. $2,000 security deposit ...

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Property Type

Sarasota House

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Sarasota House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$799

avg/night

$799
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Very inviting home with pool, fenced yard and simple walk to St Armand's Circle. A Jewel on St. Armands Circle! The location makes this spacious 3BR+Casita/3BA with a private pool in a botanical setting a perfect month long vacation spot. This residence has it all for those who want to be right ...

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Property Type

Sarasota House

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Sarasota House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
14 reviews

$393

avg/night

$393
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • WiFi

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
3 reviews

Distance to beach: 1 miles to Siesta Key

$143

avg/night

$143
avg per night
View Details

Key Amenities

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

About this property

OUR RATES: December 2024 $2400 January 2025 $4000 February-March 2025 $5000 April 2025 $3900 May-December 2025 $2400 *Calendar months only. *Ask for our 6-month plus special rate *Pet Friendly, Community pool ...

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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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Sarasota House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$746

avg/night

$746
avg per night
View Details

Key Amenities

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

About this property

Bring the whole family as this home features 3 bedrooms and 2 1/2 baths. This very spacious home is almost 2,600 square feet with plenty of room to relax. Huge open living area. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. Lot's of space. It is steps ...

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Property Type

Sarasota House

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Sarasota House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$833

avg/night

$833
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
13 reviews

Distance to beach: 0.5 miles to Turtle Beach

$214

avg/night

$214
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Looking for the perfect vacation rental? Weekly? Monthly? or for the Season? This 2 bed /1 bath 3rd floor condo has just been freshly painted with a brand new kitchen and new flooring. Features a queen size bed in one room & a KING in the other room. Large granite island in the fully equip kitchen ...

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Property Type

Sarasota Condo

Featured review

"Perfect Vacation"

What a perfect place to stay for our vacation. Perfect size, very clean, lovely kitchen island, and two balconies!! From the balcony you can see the pool, the river, and the ocean all at once. So picturesque!! ...

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Sarasota Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$872

avg/night

$872
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

exquisite furnishings, Ritz Managed building, Ritz membership access included. This home is brand new to our rental options so book quickly before its filled. Ritz-Carlton Managed "The Beach Residences" southeast corner residence is desirably positioned to capture the stunning Sarasota Bay ...

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Property Type

Sarasota Condo

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Sarasota Villa
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Enjoy a warm winter stay in this beautiful, fully furnished 2 bdr, 2 bath villa in the desirable Sarasota neighborhood of The Meadows. Primary bedroom has a king size bed, dresser, walk in closet and a large en suite bathroom with double sinks. Second bedroom has a queen size Murphy bed and desk with ...

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Property Type

Sarasota Villa

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

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

$288

avg/night

$288
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

$236

avg/night

$236
avg per night
View Details

Key Amenities

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

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 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

$116

avg/night

$116
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 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
  • Private pool
  • Rentals by owner
  • WiFi

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 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

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 Master Suite with king bed, walk-in closet, ...

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Property Type

Sarasota House

Featured review

"Excellent winter rental near Siesta Key"

My husband and I spent three months at the home of Aaron and Joanne in the winter of 2023. I believe that we were the first renters after an extensive renovation of the property. The owners were swift ...

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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

$387

avg/night

$387
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$486

avg/night

$486
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Bird Key canal front Paradise Welcome to waterfront living on one of the most desirable streets in Bird Key. A circular paver drive enveloped by lush mature landscaping frames the façade, as a double-door entry leads the way inside to its spacious and open floorplan with high ceilings in living ...

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Property Type

Sarasota House

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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

$184

avg/night

$184
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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 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.

$113

avg/night

$113
avg per night
View Details

Key Amenities

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

About this property

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 King bed, full bathroom and walk-in closets, second bedroom ...

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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 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
  • Pool
  • Rentals by owner
  • WiFi

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 House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$276

avg/night

$276
avg per night
View Details

Key Amenities

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

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 Villa
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 3 miles to Lido Beach

$126

avg/night

$126
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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

Featured review

"Truly a hidden gem"

We really love this property. We have traveled extensively and stayed in dozens of Airbnbs. This cozy condo has been superior in most every way. It is ideally located to investigate the highlights of Sarasota. ...

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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

$297

avg/night

$297
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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 House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
15 reviews

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

$149

avg/night

$149
avg per night
View Details

Key Amenities

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

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

"Enjoyed stay"

Stayed here 3 weeks in November, the house was clean and well supplied with all you could need. The pool was great and the owners were very enjoyable to deal with. The only draw back I could see was myself ...

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Sarasota Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 2 miles to Siesta Key beach

$149

avg/night

$149
avg per night
View Details

Key Amenities

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

About this property

OUR RATES: January $4200 February- March $5000 April $3000 May-December $1999 *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 ...

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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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Sarasota Villa
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 5 miles to Siesta Key Beach

$230

avg/night

$230
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Our house has a renovated kitchen with newer appliances including washer and dryer in the laundry area. The two bathrooms are also renovated. Our "American Dream" is decorated and prepared to make it feel as homely as possible. Bedroom 1 has a King bed which means that 3 can fit. In bedroom ...

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Property Type

Sarasota Villa

Featured review

"Great stay!"

Our first time staying in Airbnb. Was very skeptical but because our friends stayed in this area, we decided to give it a try. Clean house! Large living room! Everything needed for dining is clean and ...

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

SIX MONTH MINIMUM LEASE.Available starting 5/31/2025. Ability to extend rental through 12/31/2025. Dates are flexible. This fully furnished, move-in-ready, top floor 2BR/2Bath, 1365 SqFt condo, in the beautiful Orchid Oaks complex is available from 5/30/2025 through 12/31/2025. Monthly rent includes: ...

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Property Type

Sarasota Condo

Featured review

"Friendly and Peaceful"

The people throughout the complex were very nice and loved to talk to you like you knew them forever! The pool was a great center point with the setting all around it and the trees. The bridge over to the ...

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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

$138

avg/night

$138
avg per night
View Details

Key Amenities

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

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 Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

$123

avg/night

$123
avg per night
View Details

Key Amenities

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

About this property

TEMPORARY 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 ...

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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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

$141

avg/night

$141
avg per night
View Details

Key Amenities

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

About this property

2br/2ba first floor condo, Situated a short 5-minute drive from the cool emerald waters of Siesta Key Beach, on the North edge of Palmer Ranch. This tropical resort community is a relaxing oasis under the warm skies of the Gulf Coast. With its swaying palms, shimmering lake views and world-class resort ...

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Property Type

Sarasota Condo

Featured review

"Awesome place"

We loved this place. The condo is really very very clean. the decoration style beach house very pretty. The beds are comfortable. Eva the owner is a lovely person!

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Sarasota House
2 BR | 3 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 3 bathrooms
2 reviews

$391

avg/night

$391
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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 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

$128

avg/night

$128
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms

$257

avg/night

$257
avg per night
View Details

Key Amenities

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

About this property

Fantastic vacation spot with a luxurious screened in private heated pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St Armand's Circle ...

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Property Type

Sarasota House

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Sarasota Apartment
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom
2 reviews

$133

avg/night

$133
avg per night
View Details

Key Amenities

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

About this property

Newly renovated 2br/1ba, 980 sqft, 2nd floor condo in the Sienna Park, Sarasota, Fl.

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Property Type

Sarasota Apartment

Featured review

"Siesta Key"

Wonderful location right close to the beach. Lovely and well stocked with whatever you need. Tami was great!

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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

$142

avg/night

$142
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Sarasota Apartment

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Sarasota House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$135

avg/night

$135
avg per night
View Details

Key Amenities

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

About this property

WINTER RENTALS WELCOME A renovated Florida style charming paradise cottage featuring a tropical oasis backyard with large in-ground pool and bar area. This home is fully furnished and conveniently located. Enjoy a newly renovated home that includes an updated kitchen, living room, bathroom and bedrooms, ...

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Property Type

Sarasota House

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Sarasota House
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
  • Pool
  • Rentals by owner
  • WiFi

About this property

$3500 off season (May-October) - $4000 in season (November-April) 2/2 + Den/Office Fully Furnished in quiet established Beekman Place Community. Recently completely renovated. All new appliances including washer/dryer. 2 car garage. Private corner lot with mature trees, beautiful patio and fenced ...

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Property Type

Sarasota House

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Sarasota House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 4 miles to Siesta Key/Crescent Beach

$303

avg/night

$303
avg per night
View Details

Key Amenities

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

About this property

This exquisite Coastal House with all brand NEW furnishings has a beachy style with King size beds in ALL 3 bedrooms! It’s conveniently located just 3.8 miles from #1 Siesta Key Beach, only 5 miles to downtown Sarasota, just 7.5 miles to Lido Key Beach/St. Armand's Circle, 2 houses down from ...

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Property Type

Sarasota House

Featured review

"Newly Remodeled, Super Clean!"

We had a lovely stay at this newly remodeled home in Sarasota. We enjoyed morning coffee on the back patio after a great night's rest in the king size beds (three KING beds--what a bonus!), and we definitely ...

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Sarasota Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 10 miles to Lido beach

$105

avg/night

$105
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Highly desirable unit at the luxurious Serenata Condominium Residencies. Spectacular split floor plan featuring 10' ceilings, large living room with dining room and fully equipped kitchen, 2 niece bedrooms with huge walking closets, beautiful lanai with extra storage, laundry room and more.

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Property Type

Sarasota Condo

Featured review

"Wonderful home away from home!"

We have stayed in this particular unit for the past 3 winters and would return in a heartbeat if it were not for unexpected health issues recently, some of which are aggravatd by stair climbing. It is ...

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Sarasota Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 13 miles to Siesta Key Beasch

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This 2 bedroom condo located in the heart of The Meadows will delight the avid seasonal tenant or short term vacation aficionado. A first floor end unit with a prime view of the courtyard and pool and steps away from one of The Meadows golf courses. This fully furnished unit will sleep 6 people on ...

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Property Type

Sarasota Condo

Featured review

"Perfect Location in Every Way"

First of all, Sandy was great. She was so responsive, kind, answered all my questions, and just went above and beyond. I booked with Sandy before ever having visited Sarasota as I needed a place to stay ...

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Sarasota House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Beautifully furnished, spacious 3 bedroom 2 bath vacation home in the heart of Sarasota. Sunaire Terrace is a wonderful location offering close proximity to Downtown Sarasota, dining, nightlife, shopping, museums, arts and theatre. St Armand’s Circle is a short drive over the John Ringling Causeway, ...

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Property Type

Sarasota House

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Sarasota Condo
2 BR | 2 BA | Sleeps 3 | Quick View
Sleeps 3, 2 bedrooms, 2 bathrooms

Distance to beach: 4 miles to Lido

$247

avg/night

$247
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The Strand Sarasota- A waterfront oasis with: Balcony/ terrace with view of Sarasota Bay 2 bedrooms ( one is a den with sofa pullout ) , 2 full baths, a few mins from downtown Sarasota. Everything included in property : cookware, linens , WIFI, Washer / Dryer No animals or smoking- property ...

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Property Type

Sarasota Condo

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Sarasota Vacation Rentals

Monthly Rentals in Sarasota

Your Perfect Monthly Rental Awaits

Explore a diverse selection of monthly rentals tailored to meet your needs. Whether you prefer a cozy condo close to the vibrant downtown or a spacious home near the tranquil beaches, Sarasota has a variety of options to choose from. Enjoy the flexibility and comfort of a long-term rental in this beautiful coastal city.

Why Rent Monthly?

Cost Savings: Monthly rentals often come with discounted rates compared to short-term stays, making it more economical for extended vacations or work assignments.

Flexibility and Comfort: Renting monthly allows you to settle into a routine and truly experience the local lifestyle. Enjoy the comfort of a home-like environment with all the amenities you need for a long-term stay.

Stress-Free Living: With a monthly rental, avoid the hassle of frequent check-ins and check-outs. Unpack, relax, and fully enjoy your time in Sarasota without the constant need to move.

Community Feel: Staying longer helps you become part of the community. Get to know the locals, find your favorite spots, and feel more at home in Sarasota.

Book Your Monthly Rental Today

Don’t miss the chance to stay in one of the most desirable locations in Florida. Browse our listings for monthly rentals in Sarasota and find the perfect place for your extended stay. With a variety of options to choose from, you’re sure to find a rental that fits your needs and makes your stay in Sarasota unforgettable.

Plan Ahead

Thinking about next year? Secure your spot now for seasonal rentals and ensure you get the best accommodations for your stay. Whether you’re planning a winter escape or a long-term summer visit, booking early guarantees you the perfect rental.

Amenities and Perks for Longer Stays

Furnished Rentals: Fully furnished rentals include a kitchen and all the amenities you need to live comfortably for a month or longer.

Flexibility You Need: Choose your exact move-in and move-out dates and easily book online without any additional commitment or paperwork.

Simple Monthly Prices: Enjoy special rates for long-term vacation rentals and a single monthly payment without additional charges.

Work-Friendly Spaces for Digital Nomads: Find long-term stays with high-speed Wi-Fi and dedicated working spaces, perfect for traveling professionals.

Popular Amenities for Monthly Rentals

🥘 Kitchen
📶 Wi-Fi
🐾 Pet friendly
💻 Laptop-friendly workspace
🚗 Free parking on premises

Monthly Rentals in Sarasota for Any Type of Traveler

Discover the Perfect Monthly Rental for Your Group

Planning a getaway with a medium-sized or large group in Sarasota? Our selection of monthly rentals includes spacious homes designed for groups of 8 or more people. Find the ideal accommodation complete with private pools, large kitchens, and ample space to relax and enjoy. Explore options with 7+ bedrooms and multiple bathrooms to ensure everyone has room to unwind.

Family-Friendly Monthly Rentals

Looking to plan a large family trip? Sarasota offers numerous family-friendly monthly rentals equipped with amenities like private pools, game rooms, and hot tubs. Enjoy activities such as biking, swimming, hiking, and more. Find roomy rentals that can comfortably house a large family with five or more beds and multiple bathrooms. Start your search now to find the perfect family-friendly rental in Sarasota.

Romantic Getaways for Couples

Browse our best offers for couples seeking a private getaway in Sarasota. Enjoy relaxing activities like hiking, swimming, and biking. Our romantic monthly rentals come equipped with jacuzzis, spas, and picturesque views of Sarasota's beautiful scenery. Plan your couple's retreat and find the perfect place to create unforgettable memories.

Winter Getaways and Snowbirds

Winter Retreats in Sarasota

Escape the cold and enjoy the warmth of Sarasota during the winter months. Our monthly rentals are perfect for snowbirds looking to spend the winter in a sunny and pleasant climate. With average temperatures ranging from the mid-60s to mid-70s Fahrenheit, Sarasota offers an inviting escape from the winter chill.

Why Sarasota is Perfect for Snowbirds

Ideal Climate: Enjoy mild and comfortable weather throughout the winter, perfect for outdoor activities and relaxation.

Community Atmosphere: Join a vibrant community of fellow snowbirds and enjoy social activities, clubs, and events designed for winter visitors.

Healthcare and Amenities: Sarasota is well-equipped with top-notch healthcare facilities, senior-friendly amenities, and services to ensure a comfortable stay.

Recreational Opportunities: From golfing and fishing to leisurely walks on the beach, Sarasota offers a variety of recreational activities to keep you active and entertained.

Book Your Winter Stay Now

Secure your winter retreat in Sarasota by booking one of our monthly rentals. Enjoy the best that Sarasota has to offer and make your winter getaway a memorable experience. Explore our listings and find the perfect home away from home for your winter escape.

Enjoy Beach Activities in Sarasota

Sarasota boasts some of the most beautiful beaches in Florida, making it a paradise for beach lovers. When you stay in one of our monthly rentals, you'll have easy access to a variety of beach activities:

  • Swimming and Sunbathing: Relax on the soft, sandy shores and take a refreshing dip in the Gulf of Mexico's warm waters.
  • Beachcombing: Stroll along the coastline and discover an array of shells and other treasures washed ashore.
  • Water Sports: Try exciting water sports like jet skiing, paddleboarding, and kayaking.
  • Fishing: Cast a line from the shore or book a deep-sea fishing excursion to catch a variety of fish.
  • Beach Picnics: Enjoy a picnic with a view, as you dine al fresco with the sound of the waves in the background.
  • Sunset Watching: Sarasota is famous for its breathtaking sunsets. End your day by watching the sun dip below the horizon, painting the sky with vibrant colors.

Seasonal Information about Sarasota Monthly Rentals

💰 Highest rates: In March
🎉 Busiest month: January
🏠 Popular home types: Condo and House rental
🔥 Hottest months: July and August
❄️ Coldest months: January and December
Rainiest months: June and August
🌺 Best months for flowers: April and May
🌴 Peak tourist season: December to April
🍂 Quietest months: September and October
🌊 Best beach months: April and May
🏌️ Best golfing months: November to April
🎨 Top cultural events: Sarasota Film Festival (April), Sarasota Music Festival (June)
🍽️ Best dining months: January to March (Restaurant Weeks)
🦋 Nature activities peak: March to May (Butterfly watching and bird migrations)
🛶 Water sports season: June to September
🏖️ Best months for shelling: May and June
📅 Local festivals peak: December to April

Explore our listings today to find the perfect monthly rental in Sarasota, Florida, and make the most of your beachside getaway!