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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.

  • 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:

    “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.”

  • 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.”

  • Siesta key getaway!
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bathroom
    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.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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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

Stroll to Siesta Beach from Serene Condo + 2 bikes
SUPERHOSTEntire apartment
Stroll to Siesta Beach from Serene Condo + 2 bikes
Price:₹5,177 / night
Mid Century Gem, west of the trail.
SUPERHOSTEntire bungalow
Mid Century Gem, west of the trail.
Price:₹7,428 / night
Beachfront Home on Siesta Beach with pool access
Entire townhouse
Beachfront Home on Siesta Beach with pool access
Price:₹15,681 / night
Cancel at Anytime! Studio retreat on Siesta Key, steps to the beach
Entire apartment
Cancel at Anytime! Studio retreat on Siesta Key, steps to the beach
Price:₹7,053 / night
Siesta key getaway!
SUPERHOSTEntire apartment
Siesta key getaway!
Price:₹9,378 / night
OPEN IN AUG! Siesta Key, OWN ENT MBR 1 Mi away!!
Private room
OPEN IN AUG! Siesta Key, OWN ENT MBR 1 Mi away!!
Price:₹3,376 / night
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
SUPERHOSTEntire apartment
SIESTA KEY GROUND FLOOR CONDO ON TROLLEY LINE
Price:₹7,428 / night
Siesta Key Zen Den- Relax and Recharge Poolside!
Entire flat
Siesta Key Zen Den- Relax and Recharge Poolside!
Price:₹11,179 / night
POOL   1 Bed   Sea horse  Walk to beach SPECIALS
SUPERHOSTEntire flat
POOL 1 Bed Sea horse Walk to beach SPECIALS
Price:₹7,428 / night
Cozy Cottage on Siesta Key
SUPERHOSTEntire cottage
Cozy Cottage on Siesta Key
Price:₹7,053 / night
Siesta Key Cozy Cottage across from the beach!
SUPERHOSTEntire cottage
Siesta Key Cozy Cottage across from the beach!
Price:₹8,853 / night
Cute Siesta Key Cottage across from beach access!!
Entire cottage
Cute Siesta Key Cottage across from beach access!!
Price:₹11,929 / night
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