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Vacation rentals in Siesta Key

Vacation rentals in Siesta Key

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Top-rated vacation rentals in Siesta Key

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

  • Beachfront Condo! Shown on HGTV! Renovated in 2018
    SUPERHOSTEntire condominium · 4 guests · 2 beds · 1 bath
    Beachfront Condo! Shown on HGTV! Renovated in 2018

    Be one of the lucky few to call this your home for the week! This unit was shown on HGTV in April of 2019. We have included some still shots from the episode to display the unit as shown from the episode. Freshly renovated in January of 2018! The unit was renovated with new paint, floors, furniture, etc. 3 heated pools, Shuffleboard, outdoor grill, free lounge chairs directly on the beach, and much more!

    What guests are saying:

    “This is a wonderful condo - very spacious feeling. The bedroom is large with incredible storage. The king bed was very comfortable (no hip or low back pain - yeah!). The kitchen is roomy with a lot of storage and nice appliances. The living area was very comfortable and the corner entertainment unit allowed TV viewing from any angle. The place was tastefully decorated in beach & nautical theme - well done! We hope to come back!”

  • 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!!!!!”

  • Siesta key getaway!
    SUPERHOSTEntire condominium · 2 guests · 1 bed · 1 bath
    Siesta key getaway!

    perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

    What guests are saying:

    “Debbie’s place was the perfect space for my weekend getaway. The condo is in a great location, very comfortable and had everything I needed. It was really easy to get to and to get around the key from. Debbie was a great host and I would recommend her place to anyone.”

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

Siesta Key Condo with 2 QUEEN BEDS, Walk to Beach
SUPERHOSTEntire condominium
Siesta Key Condo with 2 QUEEN BEDS, Walk to Beach
Price:$89 / night
Stroll to Siesta Beach from Serene Condo + 2 bikes
SUPERHOSTEntire condominium
Stroll to Siesta Beach from Serene Condo + 2 bikes
Price:$126 / 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:$199 / night
Beach & Pool Open! Direct Beachfront. Sunset View!
SUPERHOSTEntire apartment
Beach & Pool Open! Direct Beachfront. Sunset View!
Price:$240 / night
Adorable studio close to Siesta beach!
SUPERHOSTEntire guest suite
Adorable studio close to Siesta beach!
Price:$60 / night
SIESTA KEY BEACH ACROSS THE STREET IDEAL LOCATION
SUPERHOSTEntire condominium
SIESTA KEY BEACH ACROSS THE STREET IDEAL LOCATION
Price:$149 / night
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
SUPERHOSTEntire condominium
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
Price:$100 / night
Luxury Villa, Siesta Key Beach, Sarasota, Florida
Entire villa
Luxury Villa, Siesta Key Beach, Sarasota, Florida
Price:$200 / night
Mid Century Gem, west of the trail.
SUPERHOSTEntire bungalow
Mid Century Gem, west of the trail.
Price:$89 / night
Bright and Beachy - Steps to the Water!
SUPERHOSTEntire condominium
Bright and Beachy - Steps to the Water!
Price:$208 / night
2-Floor,  2BR, 3Bath, Condo Sleeps 8 - Near Beach!
SUPERHOSTEntire condominium
2-Floor, 2BR, 3Bath, Condo Sleeps 8 - Near Beach!
Price:$99 / night
Heart of Siesta Key Village - Walk to Beach
SUPERHOSTEntire condominium
Heart of Siesta Key Village - Walk to Beach
Price:$145 / 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