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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.

  • 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:

    “Jaymes spot was nothing short of incredible. The house was very clean, and all of the pictures are exactly what it looks like. Jayme was an amazing host and replied very quickly to any questions. She also allowed us to do a late check out as our first flight was cancelled. I rate it 5/5 and Jayme a 10/10 host.”

  • 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:

    “My sister and I enjoyed a wonderful weekend in this little Siesta Key bungalow cottage. It met our needs perfectly. located in a residential area not far from the Siesta Key Village, this property has two nice bedrooms, well-supplied kitchen, living room with TV, porch furniture and grill, a little front patio and laundry facilities. It is also handicapped accessible with wide room entrances and grab bars in the bath tub (no walk-in shower). Parking is on premises. There are extra linens and plenty of storage. Our hosts have done a thoughtful and meticulous job of providing for guest comfort. The decor is attractive and the beds and living room seating comfortable. Wish we could return to enjoy it soon! Thanks for making our stay memorable!”

  • 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

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Popular amenities for Siesta Key vacation rentals

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

Other great vacation rentals in Siesta Key

Stroll to Siesta Beach from Serene Condo + 2 bikes
SUPERHOSTEntire condominium
Stroll to Siesta Beach from Serene Condo + 2 bikes
Price:$69 / night
POOL   1 Bed   Sea horse  Walk to beach SPECIALS
SUPERHOSTEntire apartment
POOL 1 Bed Sea horse Walk to beach SPECIALS
Price:$99 / night
Beachfront Home on Siesta Beach with pool access
Entire townhouse
Beachfront Home on Siesta Beach with pool access
Price:$209 / night
Mid Century Gem, west of the trail.
SUPERHOSTEntire bungalow
Mid Century Gem, west of the trail.
Price:$99 / night
Luxury Villa, Siesta Key Beach, Sarasota, Florida
Entire villa
Luxury Villa, Siesta Key Beach, Sarasota, Florida
Price:$180 / night
Cancel at Anytime! Studio retreat on Siesta Key, steps to the beach
Entire condominium
Cancel at Anytime! Studio retreat on Siesta Key, steps to the beach
Price:$94 / night
The Siesta Key
Hotel room
The Siesta Key
Price:$165 / 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:$205 / night
Siesta key getaway!
SUPERHOSTEntire condominium
Siesta key getaway!
Price:$125 / night
Cozy Cottage on Siesta Key
SUPERHOSTEntire cottage
Cozy Cottage on Siesta Key
Price:$95 / night
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
SUPERHOSTEntire condominium
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
Price:$99 / night
Bright and Beachy - Steps to the Water!
SUPERHOSTEntire condominium
Bright and Beachy - Steps to the Water!
Price:$160 / night
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