Siesta Key Vacation Rentals

(281 rentals)
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3 BR | 2 BA | Sleeps 7 | Quick View

$348

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 3 BEDROOM, 2 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA KEY VILLAGE. OPEN FLOOR PLAN WITH LOTS OF SPACE, TILE FLOORS, A PRIVATE POOL ON A CANAL. DESIGNER KITCHEN WITH SOLID WOOD CABINETS, GRANITE COUNTERTOPS AND VIKING APPLIANCES. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND ...

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Property Type

Siesta Key House

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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 ...

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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 ...

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3 BR | 2 BA | Sleeps 8 | Quick View

1

$353

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this ranch style home delivers on location and lifestyle. Featuring three bedrooms and two baths and a one-car garage, laundry room with washer and dryer. Gorgeous heated pool looks out to the grand canal, boat dock available to launch ...

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Property Type

Siesta Key House

"Beautiful!"

Siesta 4 rent was very accommodating and responsive. It was very clean and great location. Would definitely rent again! Thank you!

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1 BR | 1 BA | Sleeps 4 | Quick View

$126

avg/night

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Key Amenities

  • Pool

About this property

Beautiful ground floor unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Unit sleeps 4, 2 Cable TV's , wireless internet ( Siesta 4 Rent is not responsible for tech support), community coin laundry right outside the door, covered parking, community pool ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 7 | Quick View

15
owner special
Owner special: Please Inquire about SPECIALS for any remaining weeks this Summer!

$263

avg/night

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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 ...

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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 ...

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4 BR | 2 BA | Sleeps 8 | Quick View

$405

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

A piece of Paradise..... Come relax in this beautiful 4 Bedroom, 2 full bath pool home offering large livingroom and family room, caged heated pool and spa, (spa is non-functional and is maintained at pool temperature.) 1 car garage ( owner keeps one car in garage), washer/dryer. Home located just 1 mile ...

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Property Type

Siesta Key House

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2 BR | 2.5 BA | Sleeps 6 | Quick View

$567

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Due to circumstances out of our control, the pool on the 2nd floor in between the buildings is closed due to refurbishment . You do still have the access to the pool that is on the beach** THIS 3RD FLOOR CONDO WAS RECENTLY REFURNISHED WITH ALL ROOMS GETTING ALL NEW FURNITURE AND FURNISHINGS AND ALL BEDS ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

6

$289

avg/night

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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 ...

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Property Type

Siesta Key Condo

"Wonderful Vacation"

This was a terrific place to stay with wonderful views of the gulf. It was a very pleasant and peaceful trip. Carrie was great to work with. Once she found out about a beach project date changing, she came ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$143

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Spectacular, modern 1 bedroom , 2nd Floor unit in Siesta Key Village offers great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 1 flat screen TV. Complex offers heated community pool and laundry ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 10 | Quick View

$267

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 3 BATH UPDATED POOL HOME LOCATED IN A BEAUTIFUL SIESTA KEY NEIGHBORHOOD. HOME OFFERS NEW FURNISHINGS, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, HIGH-SPEED INTERNET WITH BOOSTER, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). ENJOY THE LARGE PRIVATE ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$285

avg/night

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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 ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

$626

avg/night

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Key Amenities

  • Air conditioning

About this property

3 Bedroom/ 3 Bath Beachfront Townhome in Siesta Village, offering beautiful sunsets from your 2 balconies. Note that the beach directly in front of the property is private and may not allow access. Public beach access is always available just a few steps away. Go a block behind the unit to all the restaurants ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

1

$209

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

This 1 bedroom is nestled in the middle of the Casa Mar complex on the Beach side of Midnight Pass Rd. Ground floor unit, gorgeous sunroom, overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car, tennis, and community laundry facilities, NO SMOKING ...

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Property Type

Siesta Key Condo

"Welcoming"

Casa Mar is a friendly beautiful get away. The unit was lovely, clean, and warm. The beautiful sand of Siesta were just steps away. I loved my stay there!

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3 BR | 2 BA | Sleeps 6 | Quick View

2

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

$379

avg/night

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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 ...

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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!

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3 BR | 2 BA | Sleeps 6 | Quick View

$683

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

** Due to circumstances out of our control, the pool on the 2nd floor in between the buildings is closed due to refurbishment . You do still have the access to the pool that is on the beach** EXPERIENCE LUXURY AT IT'S FINEST IN THIS STUNNING 2ND FLOOR CONDO WITH PARTIAL GULF VIEW FROM SIDE BALCONY. ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

22

Distance to beach: 0.1 miles to Siesta Key Beach

$135

avg/night

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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 ...

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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 ...

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3 BR | 3 BA | Sleeps 6 | Quick View

$382

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

BEAUTIFUL, PRIVATE 3 BEDROOM / 3 BATH HOME LOCATED IN THE QUIET RESIDENTIAL NEIGHBORHOOD OF SIESTA ISLES. JUST 5 BLOCKS FROM THE WORLD FAMOUS SIESTA KEY BEACH WITH EASY ACCESS. HOME IS FULLY RENOVATED AND NEWLY FURNISHED FOR YOUR ENJOYMENT WITH AN OPEN FLOOR PLAN WITH LOTS TO OFFER. FULLY EQUIPPED KITCHEN ...

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Property Type

Siesta Key House

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Key Amenities

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

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

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Property Type

Siesta Key House

"Perfect Getaway!"

We SO enjoyed our stay there! Our stay was to celebrate a milestone birthday of our sister and we couldn't have asked for a better spot! Our main goal was to relax, catch up and enjoy the beautiful beach ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$383

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. COMPLEX OFFERS 2 POOLS, TENNIS, INTERNET ACCESS ROOM, (SIESTA 4- RENT ASSUMES NO RESPONSIBILITY FOR SERVICE OR MAINTENANCE OF COMPUTERS), COMMUNITY LAUNDRY ROOM, ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 3 | Quick View

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

$277

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 ...

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Property Type

Siesta Key Condo

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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 ...

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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.

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2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 0.2 miles to Siesta Key Beach

$257

avg/night

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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 ...

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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 ...

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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 ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

1

$243

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

20% OFF DECEMBER 2023!!! WELCOME TO PARADISE! COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH GRAND CANAL HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES. THIS FABULOUS REMODELED HOME FEATURES A CUSTOM GOURMET KITCHEN AND OPEN FLOOR PLAN PERFECT FOR ENTERTAINING. HIGH-SPEED INTERNET AVAILABLE, ...

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Property Type

Siesta Key House

"522 Canal Rd"

Great vacation rental home with tile floors throughout making it a perfect beach home. The house has four bedrooms three of which have their own private, full bathroom. Siesta-4-Rent Management was great ...

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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 ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$277

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

1st Floor Duplex in the Siesta Village. This unit offers 2 Bedrooms, 2 Baths, tile floors, Leather furniture, screened lanai, washer/dryer in unit, pool shared with the 305 unit. Located in Siesta Village near all the restaurants and shops and about 2 blocks to Siesta Beach access. Unit offers high speed ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$277

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

2nd Floor, Duplex in Siesta Village. This unit offers 2 Bedrooms and 2 Baths, Shared pool with 303. washer/dryer in unit, screened lanai. Located near quaint shops and restaurants in Siesta Village and about 2 block to the Siesta Beach access. High speed internet- wifi ( Siesta 4 Rent does not offer tech ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$310

avg/night

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

GORGEOUS GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE SOUGHT AFTER CRYSTAL SANDS COMPLEX. TILE FLOORS THROUGHOUT KITCHEN, BATHS and LIVING ROOM. 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH SPEED WIRELESS INTERNET ALSO AVAILABLE, (SIESTA 4-RENT IS NOT ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$166

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

4TH FLOOR BAYSIDE, 2 BEDROOM / 2 BATH CONDO LOCATED IN THE CAPRI BUILDING OF THE EXCELSIOR COMPLEX. THE COMPLEX HAS 2 POOLS (ONE ON BEACHSIDE AND ONE ON BAYSIDE) WITH HOT TUB, 3 LIGHTED TENNIS COURTS, OUTDOOR BARBECUE / PICNIC AREA AND BEACH ACCESS. UNIT OFFERS WASHER / DRYER, HIGH SPEED INTERNET SERVICE, ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$209

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This 1 bedroom is nestled in the middle of the Casa Mar complex on the Beach side of Midnight Pass, Offering ground floor, screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car. and tennis, Community laundry facilities. Beach chairs ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

73

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

$277

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 ...

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Property Type

Siesta Key Condo

"Paradise"

Our second year booking with Dina. Fabulous location (you won’t get any closer than this to the beach ) Condo was immaculate and beautifully decorated and was equipped with all the necessities, plus ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 1 miles to Turtle Beach

$146

avg/night

View Details

Key Amenities

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

About this property

This waterfront 3 bedroom Bungalow is nestled in an upscale area on Siesta Key between Turtle Beach (1 mi.), Crescent Beach (.5 mi.) and Siesta Key Beach (3 mi.) Free trolley can transport you to the beaches and restaurant in The Village. Enjoy your private dock on beautiful Heron Lagoon watching the ...

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Property Type

Siesta Key House

"Interior Designer"

The Bungalow is well designed as a beachy vibe...great location right on Midnight Pass. It is located at the quieter end of the key which we found more relaxing...great walking. The owners of the Bungalow ...

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3 BR | 3 BA | Sleeps 6 | Quick View

$790

avg/night

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

**Any advertised discounts on website do not apply to this unit*** Due to circumstances out of our control, the pool on the 2nd floor in between the buildings is closed due to refurbishment. You do still have the access to the pool that is on the beach. also the spiral staircase from this units balcony ...

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Property Type

Siesta Key Condo

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5 BR | 3.5 BA | Sleeps 15 | Quick View

1

$789

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

This 3400 sq ft., 5 Bedroom 3 Bath, Townhome Offers, Private heated pool- **please keep in mind the pool is refreshing, but has limited space for larger parties. Many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. (REVISED LAYOUT of the HOUSE : Effective: Oct. 2019 ...

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Property Type

Siesta Key Condo

"Vacational stay"

This was a pleasant experience with the house and the pool, walking distance from the beach and the attractions, restaurants, shopping, etc: Very happy with the house: being big enough to accommodate ...

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3 BR | 2 BA | Sleeps 8 | Quick View

$267

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

CHARMING 3 BEDROOM PRIVATE HOME LOCATED IN THE QUIET SUB-DIVISION OF SIESTA ISLES. RELAX ON VACATION WITH ALL THE AMENITIES OF HOME. PRIVATE POOL, 2 CAR GARAGE, WASHER / DRYER, CHARCOAL GRILL, AND MUCH MORE. HOME OFFERS 2 LIVING ROOMS, ( ONE WITH LEATHER FURNITURE AND 53" T.V.), 6 T.V.'S, 2 ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$346

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

COME STAY AND RELAX IN THIS BEAUTIFUL 2 BEDROOM / 2 BATH CONDO LOCATED IN THE PALM BAY CLUB TOWER OVER-LOOKING THE WORLD FAMOUS SIESTA KEY BEACH, ( SAME SIZE AND VIEW AS PENTHOUSE UNIT.) ALL THE AMENITIES. FROM THE TILE FLOORING, GRANITE COUNTERTOPS AND STAINLESS STEEL APPLIANCES TO THE LEATHER FURNITURE, ...

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Property Type

Siesta Key Condo

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4 BR | 2.5 BA | Sleeps 9 | Quick View

$296

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and a one-car garage and washer and dryer. Beautiful hardwood floors, solid wood cabinetry and sleek granite countertops. ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$159

avg/night

View Details

Key Amenities

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

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...

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Property Type

Siesta Key Condo

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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. ...

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Property Type

Siesta Key Condo

"Perfect sunset beach condo"

The condo is hands down, very beautifully decorated with coastal decor. It has every amenity you will need, including a washer and dryer. It feels like you have your own private beach, very quiet and ...

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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 ...

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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!!!

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3 BR | 3 BA | Sleeps 8 | Quick View

$357

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this totally remodeled modern style home delivers on design, location and lifestyle. Featuring three bedrooms and three baths and a one-car covered parking and laundry room with washer and dryer. Beautiful polished terazzo floors, open ...

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Property Type

Siesta Key House

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 ...

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Property Type

Siesta Key Condo

"What a Fantastic Little Gem!"

Siesta Key have become our favorite vacation spot and #409 at Crescent Royale was where my wife and I got to experience the very best thanks to Karen who accepted us in her beautiful and awesomely appointed ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$197

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This adorable ground floor 1 bedroom unit in the Casa Mar complex on the beach side of Midnight Pass offers screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car. Tennisand Community laundry facilities. Beach chairs are provided by ...

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Property Type

Siesta Key Condo

Show less

Key Amenities

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

About this property

March 2024 availability, won't last long, please contact us! This condo has not been a rental in the past, so you will not see reviews yet - but you can see our property management reviews on Florida Rentals #1258, #11647, #11646 & #11645! This vacation rental condo is directly on the beach ...

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Property Type

Siesta Key Condo

"Wonderfully located, fully equipped getaway!"

This condo was perfect for our vacation with my elderly mother. It was just a few steps from the beach and had everything we needed--quality beach chairs, umbrellas. Inside was well-appointed, too. Keurig ...

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1 BR | 1.5 BA | Sleeps 3 | Quick View

$350

avg/night

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Key Amenities

  • Air conditioning

About this property

**Any advertised discounts on website do not apply to this unit*** UNIQUE 1 BEDROOM TOWNHOUSE OVERLOOKING THE BEACH, 1 BLOCK TO SIESTA VILLAGE, 3 STORY UNIT WITH GARAGE ON 1ST FLOOR AND WASHER/DRYER, BALCONY, MEXICAN TILE FLOORS, KITCHEN, SPIRAL STAIRCASE TAKES YOU TO THE MASTER SUITE ON THE 3RD FLOOR, ...

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Property Type

Siesta Key Condo

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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 ...

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Property Type

Siesta Key Condo

"Paradise"

Our family spent the first week of April basking in the sun on Turtle Beach. We thoroughly enjoyed our week’s stay at this beautiful spacious 2 bedroom 2bath condo on the Gulf of Mexico. The condo was ...

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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 ...

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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 ...

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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 400 yards to Siesta Beach

$197

avg/night

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Key Amenities

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

About this property

Spectacular long Siesta beach and Gulf of Mexico views from this gorgeous 2 BD, 2 bath unit. It has was fully remodel in a high quality fashion. The unit is furnished first class and with all the features you could want for a fun vacation! The resort style condominium has three pools, large ponds, lighted ...

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Property Type

Siesta Key Condo

"Great property !"

Beautiful home with all the amenities. Very private location on Azure Way in great neighborhood, but still close to beach & restaurants. Excellent communication with David & owners. Highly recommend.

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2 BR | 2 BA | Sleeps 6 | Quick View

6

Distance to beach: 0.2 miles to Siesta Key

$203

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 ...

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Property Type

Siesta Key Condo

"Perfect gulf and bay Siesta Key condo"

This two bedroom Palm Bay Club condo has it all. It was exactly as described in the listing. We had everything we needed for a stress free comfortable stay. The beds were the most comfortable we have slept ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$221

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

1 BEDROOM, 1ST FLOOR CONDO W/ PRIVATE SCREENED LANAI, NEW PERGO FLOORS, NEW KITCHEN, WASHER/ DRYER IN UNIT. LOCATED ONLY 1 BLOCK FROM THE SHOPS AND RESTAURANTS IN THE VILLAGE, 1 BLOCK TO THE BEACH, SEPARATE DINING ROOM, HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). POOL ...

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Siesta Key Condo

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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 281 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 $58 per night with an average price per night of $256.

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 59 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 56 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!