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Vacation rentals in Siesta Key

Vacation rentals in Siesta Key

Find and book unique accommodation on Airbnb

Top-rated holiday 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 bathroom
    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!!!!!”

  • Stroll to Siesta Beach from Serene Condo + 2 bikes
    SUPERHOSTEntire apartment · 4 guests · 1 bed · 1 bathroom
    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!”

  • Mid Century Gem, west of the trail.
    SUPERHOSTEntire bungalow · 4 guests · 2 beds · 1 bathroom
    Mid Century Gem, west of the trail.

    This is wonderful one bedroom house, perfect for your next getaway. Its located west of the trail within walking distance to Starbucks and other stores and restaurants. Its century located between the two brides to Siesta Beach also 5 minutes away from downtown and other attractions. Mid Century Gem.

    What guests are saying:

    “I can recommend this place to anyone visiting sarasota. Its convenient located near to downtown and siesta key beach. This house provides all the necessities to have a lovey stay. Only one comment on the cleanliness, there were some hairs on the couch and in the bathroom.”

Holiday rentals for every style

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Popular amenities for Siesta Key holiday rentals

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

Other great holiday rentals in Siesta Key

Beach & Pool Open! Direct Beachfront. Sunset View!
SUPERHOSTEntire flat
Beach & Pool Open! Direct Beachfront. Sunset View!
Price:€196 / night
Cottage on Siesta Key FL
SUPERHOSTEntire cottage
Cottage on Siesta Key FL
Price:€103 / night
Beachfront Condo! Shown on HGTV! Renovated in 2018
SUPERHOSTEntire apartment
Beachfront Condo! Shown on HGTV! Renovated in 2018
Price:€113 / night
Siesta Key, large family home.
SUPERHOSTEntire house
Siesta Key, large family home.
Price:€354 / night
5209B Calle Menorca - Amazing Pool or Siesta Key Beach?  You Choose with this Perfectly Located Condo in Siesta Key Village
SUPERHOSTEntire apartment
5209B Calle Menorca - Amazing Pool or Siesta Key Beach? You Choose with this Perfectly Located Condo in Siesta Key Village
Price:€185 / night
Siesta key getaway!
SUPERHOSTEntire apartment
Siesta key getaway!
Price:€115 / night
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
SUPERHOSTEntire apartment
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
Price:€88 / night
Bright and Beachy - Steps to the Water!
SUPERHOSTEntire apartment
Bright and Beachy - Steps to the Water!
Price:€185 / night
"Safe & Clean"  Our Beach House
SUPERHOSTEntire house
"Safe & Clean" Our Beach House
Price:€338 / night
Siesta Gardens @ Siesta Key Village
SUPERHOSTEntire apartment
Siesta Gardens @ Siesta Key Village
Price:€176 / night
#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf
SUPERHOSTEntire apartment
#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf
Price:€136 / night
Private Crescent Beach Escape- Beach is OPEN
SUPERHOSTEntire apartment
Private Crescent Beach Escape- Beach is OPEN
Price:€203 / night
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