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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!!!!!”

  • 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!”

  • Beach & Pool Open! Direct Beachfront. Sunset View!
    SUPERHOSTEntire apartment · 6 guests · 3 beds · 2 baths
    Beach & Pool Open! Direct Beachfront. Sunset View!

    Amazing direct Gulf view from this 4th floor front corner condo. Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. We are right on the beach with lounge chairs provided. As close as you can get to the Gulf without being in the water! We can comfortably accommodate 6 people. There are 2 double beds in one room and 1 King in the other.

    What guests are saying:

    “Tracy and Pavan truly lived up to their SuperHost status! Their communication with us, both before and during our stay, was beyond compare, while not at all intrusive. The condo was beautiful, spotlessly clean, and had an incredible view of the beach and water. The beds were comfortable, and the bedrooms had nice dressers and ample closet room. The building was well-managed and it was about 50 steps directly onto the absolutely gorgeous beach. It was simply a perfect vacation and I can't speak more highly of Tracy and Pavan's condo and their hosting! Elle”

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:ﺩ.ﺇ327 / night
Cottage on Siesta Key FL
SUPERHOSTEntire cottage
Cottage on Siesta Key FL
Price:ﺩ.ﺇ433 / night
Beachfront Condo! Shown on HGTV! Renovated in 2018
SUPERHOSTEntire condominium
Beachfront Condo! Shown on HGTV! Renovated in 2018
Price:ﺩ.ﺇ407 / night
Siesta key getaway!
SUPERHOSTEntire condominium
Siesta key getaway!
Price:ﺩ.ﺇ478 / 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:ﺩ.ﺇ717 / night
Bright and Beachy - Steps to the Water!
SUPERHOSTEntire condominium
Bright and Beachy - Steps to the Water!
Price:ﺩ.ﺇ720 / night
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
SUPERHOSTEntire condominium
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
Price:ﺩ.ﺇ365 / night
Siesta Key, large family home.
SUPERHOSTEntire house
Siesta Key, large family home.
Price:ﺩ.ﺇ1,469 / night
Siesta Gardens @ Siesta Key Village
SUPERHOSTEntire condominium
Siesta Gardens @ Siesta Key Village
Price:ﺩ.ﺇ735 / night
Private Crescent Beach Escape- Beach is OPEN
SUPERHOSTEntire condominium
Private Crescent Beach Escape- Beach is OPEN
Price:ﺩ.ﺇ861 / night
#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf
SUPERHOSTEntire condominium
#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf
Price:ﺩ.ﺇ569 / night
"Safe & Clean" Palm Oasis - Relax in comfort!
SUPERHOSTEntire house
"Safe & Clean" Palm Oasis - Relax in comfort!
Price:ﺩ.ﺇ1,833 / night
Show all

Learn more about Siesta Key

What types of vacation rentals are available in Siesta Key?

Here in Siesta Key, there are plenty of options for places to stay. Here are a few examples:
  • Houses (281 rentals)
  • Apartments (84 rentals)
  • Resorts (55 rentals)

Are there houses with pools?

Who doesn’t want a pool at their house? Here in Siesta Key, you’ll find 232 houses that have pools.

What are the top attractions in Siesta Key?

Locals agree that these attractions are worth a visit:
  • Siesta Beach (115 rentals)
  • Siesta Key Drum Circle (94 rentals)
  • Crescent Beach (402 rentals)
  • Sarasota Beach (341 rentals)
  • Siesta Key Beach Parking Lot (126 rentals)

What are some kid-friendly activities in Siesta Key?

Locals agree—these are all great places to take the kids:
  • Siesta Beach
  • Sarasota Beach
  • Siesta Key Drum Circle
  • Siesta Key Village
  • Crescent Beach

What are the top places to eat in Siesta Key?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • The Cottage
  • Daiquiri Deck South Siesta
  • Summer House Steak & Seafood
  • Restaurant Bonjour French Cafe
  • 3.14 Pi Craft Beer & Spirits