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Vacation rentals in Siesta Key

Vacation rentals in Siesta Key

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Cozy Cottage on Siesta Key
    SUPERHOSTEntire cottage · 5 guests · 2 beds · 1 bath
    Cozy Cottage on Siesta Key

    SARASOTA BEACH IS OPEN!! Come enjoy island living on Siesta Key. Florida bungalow-2 bedrooms, 1 bathroom, open kitchen with dining area, a patio area with a bbq to enjoy dinner after a day at the beach! We have beach towels, beach chairs and coolers too. It is light, bright, clean and has an open floor plan. There is WiFi and cable TV. Located on a quiet street only 4 blocks to Siesta Village with cute shops and restaurants. Welcome!

    What guests are saying:

    “This is such a charming clean and top notch house to stay in! We loved it. Off the busy beaten path of Siesta but so easy to breeze into the Village and go to the beaches. Evelyn provides all kinds of extras like lots of beach towels, chairs, and umbrella. Inside laundry was such a plus too. Roomy little house with a great open set up and nice roomy kitchen. We loved our stay!!!!!”

  • Cottage on Siesta Key FL
    SUPERHOSTEntire cottage · 6 guests · 3 beds · 2 baths
    Cottage on Siesta Key FL

    The number one beach in the United States. Siesta Key beach is steps away. The cottage was built from the ground up completed in 2016. Brand new everything! (URL HIDDEN)

    What guests are saying:

    “Have no doubts or worries with this property. Very responsive and helpful host. Location is awesome, a very small walk across the road to the beautiful beach. Clean swimming pool on site with tikki hut for cook outs/shade. Accommodation was very clean, had all the amenities and lovely outside sitting area. I will be staying here again and would certainly recommend to anyone else.”

  • Stroll to Siesta Beach from Serene Condo + 2 bikes
    SUPERHOSTEntire condominium · 4 guests · 1 bed · 1 bath
    Stroll to Siesta Beach from Serene Condo + 2 bikes

    Relax in your ultra-private corner unit condo with amazing natural light & contemporary decor +private lanai. Enjoy the soft white sand & tropical vibes at Siesta Key Beach. This condo is located on the east side of Midnight Pass Rd, with the open air trolley stop out front *please note there is not direct private beach access: -beach wagon & gear -BIKES ($30 per bike entire stay) -Pool -closed until April 30th -Reserved parking -Washer & Dryer -Tennis courts/Dock

    What guests are saying:

    “Jayme was quick to respond, check in was easy, the apartment was clean and the bed is very soft and comfy. The location is great if you don't mind a bit of a walk to the beach. The trolley is great when it's running. But unfortunately it wasn't running memorial day wknd yet. We had a great stay and the bikes were nice too. All you need for a lovely weekend!”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Siesta Key vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Siesta Key

Mid Century Gem, west of the trail.
SUPERHOSTEntire bungalow
Mid Century Gem, west of the trail.
Price:€83 / night
Beach & Pool Open! Direct Beachfront. Sunset View!
SUPERHOSTEntire apartment
Beach & Pool Open! Direct Beachfront. Sunset View!
Price:€221 / night
Beachfront Condo! Shown on HGTV! Renovated in 2018
SUPERHOSTEntire condominium
Beachfront Condo! Shown on HGTV! Renovated in 2018
Price:€114 / night
Siesta key getaway!
SUPERHOSTEntire condominium
Siesta key getaway!
Price:€120 / night
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
SUPERHOSTEntire condominium
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
Price:€89 / night
Bright and Beachy - Steps to the Water!
SUPERHOSTEntire condominium
Bright and Beachy - Steps to the Water!
Price:€144 / night
5209B Calle Menorca - Amazing Pool or Siesta Key Beach?  You Choose with this Perfectly Located Condo in Siesta Key Village
SUPERHOSTEntire condominium
5209B Calle Menorca - Amazing Pool or Siesta Key Beach? You Choose with this Perfectly Located Condo in Siesta Key Village
Price:€187 / night
Siesta Gardens @ Siesta Key Village
SUPERHOSTEntire condominium
Siesta Gardens @ Siesta Key Village
Price:€178 / night
Siesta Key, large family home.
SUPERHOSTEntire house
Siesta Key, large family home.
Price:€356 / night
Private Crescent Beach Escape- Beach is OPEN
SUPERHOSTEntire condominium
Private Crescent Beach Escape- Beach is OPEN
Price:€216 / night
Siesta Suite at Moonbeam Manor
Entire guest suite
Siesta Suite at Moonbeam Manor
Price:€94 / night
#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf
Entire condominium
#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf
Price:€156 / night
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