Siesta Key Vacation Rentals

(279 rentals)
booking message booking message

Key Amenities

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

About this property

This charming Siesta Key vacation rental home offers a beautiful kitchen, dining area, living room, and outdoor patio. The property includes access to a heated pool shared between the two units in the house. Located in the heart of Siesta Key Village, it's just a 3-minute walk to the #1 beach in ...

View all property information

Property Type

Siesta Key Apartment

Show less

$311

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of ...

View all property information

Property Type

Siesta Key Condo

Show less

Key Amenities

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

About this property

This colorful and well cared for unit has a new owner! The view from your lanai will include sunset and will be magnificent! No other property on Siesta Key is built this close to the Gulf of Mexico where you can hear the waves from your lanai and master bedroom windows. The furnishings are very comfortable ...

View all property information

Property Type

Siesta Key Condo

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$351

avg/night

View Details

Key Amenities

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

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

View all property information

Property Type

Siesta Key Condo

"Wonderful place to stay!"

Recently, we stayed at a Fisherman’s Cove for Spring Break. What a wonderful place to stay! Close to the ocean/beach and the condo had everything we needed!

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$311

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLTop beachfront unit at Fisherman's Cove!! Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, ...

View all property information

Property Type

Siesta Key Condo

Show less

2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 850 feet to Crescent Beach

$160

avg/night

View Details

Key Amenities

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

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #532 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed ...

View all property information

Property Type

Siesta Key Condo

"Great stay in siesta keys"

This 2 bedroom ground floor condo was comfortable, clean, stylish and centrally located. It was fully stocked eith cleaning and cooking supplies as well as hairdryer and iron. We had a great time and ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 250 feet to Crescent Beach

$285

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Direct-with-Owner Rentals: Siesta Breakers #603 offers "All-In Price" 15% to 30% Discounted Rental Rates from $1,958 to $3,708 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $420 to $913 /Wk from the listed Siesta ...

View all property information

Property Type

Siesta Key Condo

"Lovely"

The condo was very clean and comfortable. Beautiful view from the lanai. Great location, walking distance to many restaurants and ice cream parlors!

See all reviews

Show less

Key Amenities

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

About this property

Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6)If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience ...

View all property information

Property Type

Siesta Key Condo

"Wonderfully Relaxing"

Staff, wonderful, front desk also wonderful. Snythyou need is a call away. Condo comfortable and clean

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...

View all property information

Property Type

Siesta Key Condo

"good place"

Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate

See all reviews

Show less

Key Amenities

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

About this property

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of ...

View all property information

Property Type

Siesta Key Condo

Show less

2 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.0 miles to Siesta Key

$249

avg/night

View Details

Key Amenities

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

About this property

Escape to your private oasis on Siesta Key! This spacious villa offers the best of both worlds: direct access to the #1-rated Siesta Key Beach through your own private beach area, and stunning views of the Intracoastal Waterway where you can watch boats go by or launch your own kayak.Unwind in comfort ...

View all property information

Property Type

Siesta Key Villa

Show less

Key Amenities

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

About this property

Updated 2 bedroom unit in charming Casarina complex is located directly on the crystal white sands of Siesta Key Beach. Amenities galore! Magnificent gulf views. Enjoy the serenity of this casual, comfortable and tastefully decorated home away from home. You will enjoy having the In unit laundry, ...

View all property information

Property Type

Siesta Key Condo

"Siesta Key Serenity"

I absolutely loved my stay. The condo was impeccable and the sunsets were gorgeous. I highly recommend this unit. The master suite was so lovely. We really enjoyed the pool, spa, and trips to the Village.

See all reviews

Show less

Key Amenities

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

About this property

If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the ...

View all property information

Property Type

Siesta Key Condo

"Beware of Horrible Communication"

My husband and I intended to stay here in early February. On several occasions we reached out to customer service regarding damage from the hurricane. A letter was sent that only said “some amenities ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 0.2 miles to Siesta Key Beach

$265

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom ...

View all property information

Property Type

Siesta Key Condo

"Gulf and Bay Bayside Unit #1344 D"

Lovely 2B/2B ground floor condo with fabulous sunroom getting morning sunshine. Sunroom faces a shell path that winds throughout the development and views lush landscape with blooming hibiscus bushes. Quiet ...

See all reviews

Show less

Key Amenities

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

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

View all property information

Property Type

Siesta Key Condo

"Just what we wanted."

Just returned from a week in Karen’s condo. Her place is perfect. The balcony and view were wonderful. Sitting and looking at the beach was so relaxing. The condo was great. Gave you a beach feeling. ...

See all reviews

Show less

4 BR | 3.5 BA | Sleeps 6 | Quick View

5

Distance to beach: 0.3 miles to Crescent Beach

$314

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

6828 Midnight Pass Road is a townhouse style condo three level unit with 3 main bedrooms plus a bonus bath and laundry on the ground floor. Each bedroom has a queen bed, and all furniture and mattresses were purchased new in 2020. Brand new exterior paint and roof in 2024.Convenient and Easy: 3-minute ...

View all property information

Property Type

Siesta Key Townhome

"Best vacation ever!!"

We cant say enough about how beautiful this townhouse was, fully stocked with everything, (the blender was great to have because we love our mudslides out by the private pool) The location was unbelievable, ...

See all reviews

Show less

Key Amenities

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

About this property

Our villa is located in Siesta Key, FL on Crescent (Siesta Key) Beach, FAMOUS for its powdery, sugar white sand and being VOTED #1 Beach in USA. The Beach has complimentary shade cabanas and beach chairsFeatures include 2 Bedrooms, 1Bath sleeping six with 1King and 2 queen beds. The kitchen is furnished ...

View all property information

Property Type

Siesta Key Villa

"Enjoyable VacationVilla"

The Villa was perfect for my December trip to Siesta Key! Very clean, appreciated lots of towels (which I find a plus staying other places they skimp on them), kitchen well equipped. Access to the beach ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$260

avg/night

View Details

Key Amenities

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

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

View all property information

Property Type

Siesta Key Condo

Show less

Key Amenities

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

About this property

This magnificent unit is on the third floor with spectacular unobstructed views of the Gulf! This unit has been completely renovated with beautiful natural stone tile throughout, updated kitchen and bathroom and brand new furniture, coastal pictures, decorative accessories, bedding, new paint throughout. ...

View all property information

Property Type

Siesta Key Condo

"Just Perfect"

Location was amazing - views spectacular, nothing separating us from the beautiful gulf. Condo - was missing nothing and needed nothing additional. Clean. Stocked. Convenient. Comfortable. Owners - ...

See all reviews

Show less

Key Amenities

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

About this property

This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...

View all property information

Property Type

Siesta Key Condo

"Family Vacation"

Great place. I loved that I could exit my unit and be steps away from the water. The unit was very nice. Everything was great. Very clean. We were a large party and rented three of the units and everyone ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

22

Distance to beach: 0.1 miles to Siesta Key Beach

$200

avg/night

View Details

Key Amenities

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

About this property

NEWLY UPGRADED - BEAUTIFUL CONDO FOR THE PERFECT GETAWAY FROM THE COLD Right across from Siesta Key Beach, minutes from Siesta Key Village - or the South Village - shopping, top restaurants, live music, and entertainment. Walk , bike or take the free trolley.Sit on the balcony for a quiet and ...

View all property information

Property Type

Siesta Key Condo

"Great location, great property, and a ton of fun activities nearby!!"

The property has two rooms with their own bathrooms and it was perfect for what we needed. Choosing whether to spend time at the pool, beach across the street or playing pickleball, also across the street ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

View all property information

Property Type

Siesta Key Condo

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

8

Distance to beach: 0.2 miles to Siesta Key

$274

avg/night

View Details

Key Amenities

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

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach ...

View all property information

Property Type

Siesta Key Condo

"Great place!"

This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

78

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$299

avg/night

View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

View all property information

Property Type

Siesta Key Condo

"PERFECT BEACH CONDO"

This condo was amazing! The hosts were very polite and responsive. The condo was clean and well-equipped with everything we needed, including a beach wagon, chairs, sand toys, umbrellas, a boogie board, ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

8

Distance to beach: 150 yards to Crescent Beach

$266

avg/night

View Details

Key Amenities

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

About this property

1 Week Minimum Stay Required except during Feb 1 to the first Saturday after Easter when 2 weeks are required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great ...

View all property information

Property Type

Siesta Key Condo

"Georgious Siesta Key Condo"

This condo is perfectly located in the middle of Siesta Key, on the beach. It is a short distance to Siesta Key Village, that has shopping and restaurants. The condo is very comfortable, with up to date ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 600 yards to Siesta Key Beach

$244

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

There's plenty of room for everyone here at Our House. We have a split-level living area facing a large screen HDTV, so anytime you need a little down time from all the outdoor fun, settle in with your favorite movie, a bowl of popcorn, and frosty drinks. The kitchen's just a few steps away, ...

View all property information

Property Type

Siesta Key Townhome

"Great Stay"

We had a great stay at this condo. We would definitely stay here again. It was clean and spacious. It was also very close to siesta beach and near siesta village. Overall great experience!

See all reviews

Show less

Studio | 2 BA | Sleeps 4 | Quick View

$500

avg/night

View Details

Key Amenities

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

About this property

Comfortable and peaceful home with private saltwater pool and hot tub, 1.4 miles from the beach; 1 mile to the village. I have beach gear. Plenty of chairs, an umbrella, towels and coolers. Beautiful private back yard with grill and smoker in quiet neighborhood. Very comfortable and peaceful retreat. ...

View all property information

Property Type

Siesta Key House

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

7

$336

avg/night

View Details

Key Amenities

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

About this property

This colorful custom2rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit.From the modern kitchen, you will enjoy Siesta ...

View all property information

Property Type

Siesta Key Condo

"perfect spot"

Fisherman's cove is the ultimate spot for a peaceful getaway. Your host Carrie is a wonderful, warm and thoughtful person. You won't find anyone better. Her condo Is perfectly located on the corner of the ...

See all reviews

Show less

Key Amenities

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

About this property

This updated Villa is on the beach side of Siesta Key, with private beach!!!Newly renovated private villa! Beautiful brand new kitchen with quartz countertops and stainless steel appliances. All new flooring through out and newly decorated!Be one of the first guests in this newly renovated clean ...

View all property information

Property Type

Siesta Key Villa

"Highly Recommend!"

I would highly recommend renting through Ruth. Her villa was in the perfect location, with great beach access and it was newly renovated! Ruth was easily accessible and answered every question I had. The ...

See all reviews

Show less

Key Amenities

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

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

View all property information

Property Type

Siesta Key Condo

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...

See all reviews

Show less

Key Amenities

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

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

View all property information

Property Type

Siesta Key Condo

"Beauty at the Beach"

I highly recommend condo 601 South/ Beauty at the Beach! Elaine was very accommodating and her condo was the most coziest, beautiful, and relaxing place that I have stayed in a very long time. It had everything ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...

View all property information

Property Type

Siesta Key Condo

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

View all property information

Property Type

Siesta Key Condo

"Jamaica Royal"

We loved our stay here. Right on the beach and great pool close to our condo. Clean and spacious. Maybe could use a few updates but we were mainly here at night for sleeping so it worked well for us.

See all reviews

Show less

Key Amenities

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

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...

View all property information

Property Type

Siesta Key Condo

"Cold escape"

We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!

See all reviews

Show less

4 BR | 4.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.3 miles to Siesta Beach

$545

avg/night

View Details

Key Amenities

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

About this property

This 4 bedroom 4.5 bathroom condo with elevator, pool and private beach access. No need to look any further as luxury awaits! This unit can be combined with the adjoining unit for 8 bedrooms total. There is a wonderful outdoor living space with dining table and lounging area, living room, dining area, ...

View all property information

Property Type

Siesta Key Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

NEWLY RENOVATED IN 2023!!VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS,VILLA SLEEPS 8, 1 KING, 1 QUEEN, ...

View all property information

Property Type

Siesta Key Villa

"It Doesn’t Get Any Better"

I cannot tell you how amazing the property is! Half a mile walk to a gorgeous beach, a 5 minute drive to the #1 beach in the US, shopping close by, great restaurants, an amazing pool, wonderful outdoor ...

See all reviews

Show less

Key Amenities

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

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...

View all property information

Property Type

Siesta Key Condo

"You WILL NOT be disappointed with this condo!!!"

I have nothing but rave reviews of this rental - the location, the condo itself and the owners. We had an amazing time and they had anything and everything that you could want in the condo. We will definitely ...

See all reviews

Show less

Key Amenities

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

About this property

Take it easy at this mid-century modern peaceful Siesta Key Beach family & pet friendly getaway. 3 BD, 2 BA’s & 2 outdoor showers to wash off the sand after beach fun. Don’t forget to bring Fido! Hang out by the fire pit in the evenings while you grill out taking in the ocean air with ...

View all property information

Property Type

Siesta Key House

"Paradise"

The home on Siesta Key is totally amazing in every aspect. The completely updated modern architecture combined with the lush tropical landscape make this an excellent choice to relax and experience ...

See all reviews

Show less

2 BR | 1.5 BA | Sleeps 4 | Quick View

31

Distance to beach: 200 yards to Crescent Siesta Key Beach

$207

avg/night

View Details

Key Amenities

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

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

View all property information

Property Type

Siesta Key Condo

"Great place!"

Great place to stay! Has everything you need for a great beach stay. The condo was clean, decorated nicely, and offered beach supplies. It was only a short walk to the beach as well. The host was great ...

See all reviews

Show less

$217

avg/night

View Details

Key Amenities

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

About this property

Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedrooms, and beautiful crown molding throughout. The kitchen is a chefs dream, ...

View all property information

Property Type

Siesta Key Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

View all property information

Property Type

Siesta Key Condo

"Beautiful Condo in a nice quiet area a stone's throw from the beach."

We loved this condo. It was beautiful, newly refurbished and so comfortable. More like a nice family home than just a rental. We loved sitting in the sun on the lanai watching the birds and the beach. ...

See all reviews

Show less

Key Amenities

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

About this property

This vacation rental condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims. We are excited to announce that B108 has recently been ...

View all property information

Property Type

Siesta Key Condo

"Outstanding"

This is our third year in a row staying at Fishermans Cove. Our first year we were in a second floor condo these last two years we had ground floor and wouldn’t have it any other way. Everything is spotless, ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

$218

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an Olympic size pool, three lighted tennis courts, pickleball nets. ...

View all property information

Property Type

Siesta Key Condo

"Unit 403"

The place is absolutely beautiful. Great views and amenities! Close to walking distance to most things. Would definitely stay here again!

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

3

$159

avg/night

View Details

Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

View all property information

Property Type

Siesta Key Condo

"Very nice host and home. Home needs work."

The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed ...

See all reviews

Show less

Key Amenities

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

About this property

The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf from your master bedroom. Enjoy dining on the lanai while watching the sunset. During the day you can see dolphins, kite boarding and sea birds. This unit has all the comforts of home plus a full size ...

View all property information

Property Type

Siesta Key Condo

"Clean & Well Stocked"

Three very important things to make your vacation complete; cleanliness is number one of course, location and is the rental property well stocked so you have everything that is needed for a vacation of ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

View all property information

Property Type

Siesta Key Condo

"Beach and ocean waves"

The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not ...

See all reviews

Show less

Key Amenities

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

About this property

The lifestyleLive the Siesta Key lifestyle: • Short walk to the beautiful white sand beaches • Linger in the vibrant cafes and shops of The Village • Kayak along the key’s Grand Canal • Spend afternoons relaxing in the pool • Enjoy Siesta’s famous sunsets ...

View all property information

Property Type

Siesta Key House

Show less

2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 950 feet to Crescent Beach

$160

avg/night

View Details

Key Amenities

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

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #714 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed ...

View all property information

Property Type

Siesta Key Condo

"Siesta Key Midnight Cove 714, Convienient, 1st Floor Condo, Great Complex"

Midnight Cove has all the amenities for a great getaway on Siesta Key. The complex has great beach access, beach chairs with attendant on the beach, nice pool ,fitness center and two BBQ grill areas. The ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

4

Distance to beach: 0.1 miles to Siesta Beach

$286

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

Our new unit are truly a site to see. 2 BR / 2 BATH completely remodeled, newly furnished unit with fully equipped kitchen, cable TV, WiFi, and washer/dryer. Enjoy a Resort Style pool area beautifully landscaped with 2 Tiki Bars and plenty of space to work on your tan! Not to mention a grassed area for ...

View all property information

Property Type

Siesta Key Condo

"Paradise"

Our rental was perfect. Clean. Well stocked. The mgmt was awesome w communication and our only issue was a missing hdmi cable for the tv. No big deal but they felt it was and immediately fixed the issue. ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

View all property information

Property Type

Siesta Key Condo

"Beautifully renovated beach condo"

The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.

See all reviews

Show less

Map
Expand map Close map
Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

Find the Beach Vacation of a Lifetime with Siesta Key Vacation Rentals


Interested in a beach vacation for your next spring break or a long weekend away? Though the great state of Florida is known for its many scenic beach towns, there are some that cater more to those looking for a quiet, relaxing trip and some that are perfect for an exciting vacation full of non-stop fun in the sun. What if you could find a beach city that offers the best of both worlds for a truly well-rounded vacation? Enter Siesta Key vacation rentals. 

Nestled just south of Sarasota, Siesta Key, FL, is a spirited city along the Gulf Coast that offers just as many opportunities for R&R as it does for nightlife, watersports, and unforgettable adventures in the great outdoors. Though the island of Siesta Key itself is only about eight miles long, it’s jam-packed with enticing restaurants, unique shops, and glittering white sand beaches as far as the eye can see. 

As a major vacation destination along Florida’s Gulf Coast, there are many hotel options to choose from during your stay, with varying proximities to the beach. However, if you’re looking for a truly immersive experience during your trip to Siesta Key, you won’t get it at a crowded commercial hotel! 

Browse Siesta Key vacation rentals from FloridaRentals to find the perfect rental home for your beach vacation. Whether you’re looking for a sunny, romantic getaway for you and a loved one, or you’re bringing the whole family along, you’re sure to find an incredible property. Look for one that offers authentic local architecture, plenty of space to spread out during your downtime, and close proximity to all of the best features the city has to offer.

Siesta Key, Florida Travel Tips


There’s a reason why oceanside Florida cities like Siesta Key tend to be popular destinations during springtime. While temperatures may be warmest on average in the summer months, this time of year also has the highest levels of precipitation and humidity. Unfortunately, this makes it more difficult to enjoy outdoor activities. 

In mid to late spring, temperatures in the air and water are warm and comfortable without too much rain or humidity expected. This makes it easy to take part in all of your favorite pastimes, including surfing, boating, wakeboarding, or simply catching some rays on the sand. 

The closest airport to Siesta Key is the Sarasota/Bradenton International Airport, which lies around 11 miles north of the city center. Most visitors will fly into this airport for its easy access, though the area can also be reached relatively quickly by way of the Tampa International Airport.

How to Spend Your Vacation to Siesta Key House Rentals


It’s no surprise that most Siesta Key vacationers spend more time at the beach than anywhere else during their visits. The most popular beach destination is Siesta Key Beach, which was ranked the #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards in 2020. The gentle waves, powdery white sand, ample parking, and plentiful concession stands are just some of the reasons why many visitors choose to lounge their day away at Siesta Key Beach. 
Those who are interested in an unforgettable outdoor experience shouldn’t miss out on a trip out on the water with Adventure Kayak Outfitters. You’ll have the choice of a guided kayak tour of the nearby Exotic Mangrove Tunnels or a kayak rental to make your own adventure. You’re sure to spot some incredible wildlife like dolphins, exotic birds, and manatees along the way.

Yearly Events in Siesta Key


Siesta Key is closely linked with the nearby city of Sarasota. The two cities share many of their annual events, creating even bigger and better celebrations for locals and tourists alike to enjoy. 

One annual event that’s already become a mainstay in the local culture is the Annual Downtown Sarasota Craft Festival. This unique arts and crafts show features a wide variety of media, including pottery, paintings, jewelry, photography, and much more, alongside the scenic white-sand beaches. Visitors can peruse and purchase unique wares from local artisans, including soaps, spices, plants, and even kettle corn. 
Runners visiting Siesta Key can get in a great workout while supporting a great cause at the Annual Andrew Monroe Memorial Scholarship 5K Run/Walk. All funds raised during this event are donated to the Sarasota Community Foundation Scholarship, which helps local athletes train to their full potential and achieve their goals.  

Best Eats Near Siesta Key Rentals


Whether you’re in need of some casual seaside grub for the family after a long day at the beach or looking forward to a romantic date night with your significant other, Siesta Key has a huge variety of delicious and eclectic eateries fit for every taste and occasion. 

For a hearty steak, you can’t do much better than Summer House Steak & Seafood. This stylish eatery offers sustainably sourced steaks alongside a variety of unique sides, salads, beverages, and desserts that are sure to satisfy. Additionally, Summer House offers a full menu of seafood dishes. It takes full advantage of the city’s close proximity to fresh seafood and offers plenty of surf and turf options for hungry visitors. 

Island House Tap and Grill is a local favorite for casual yet memorable eats in Siesta Key. With a varied menu that includes everything from tacos to burgers to ceviche, as well as plenty of refreshing cocktails, you’re sure to enjoy a delicious and satisfying dinner with your family.


FAQ

How many vacation rentals are there in/around Siesta Key?

There are 279 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to house 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 Siesta Key?

There are vacation rentals available in Siesta Key for as low as $113 per night with an average price per night of $273.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 60 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 57 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!