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Vacation Rentals & Beach Rentals in Siesta Key

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341 beach rentals

goldeneye luxury private family plantation house

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$318

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$226

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$126

Firethorn 320 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Private outdoor pool (heated)

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Price per night from

$224

Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs

Siesta Key house

2 bedrooms / 3 bathrooms / sleeps 6

“Fantastic house close to everything” We stayed in Siesta key for the first week of November. This house was beautiful and equipped with everything you could ever need especially the heated pool and hot tub. we walked a block every evening to the village and every morning two blocks to the beach. Will book again for sure

Match: Private outdoor pool (heated)

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Price per night from

$331

Buttonwood 462 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$243

Chinaberry 943 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$156

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 14 minutes

Match: Private outdoor pool (heated)

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Price per night from

$370

Firethorn 333 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$224

Firethorn 610 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$129

Doveplum 623 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$151

Buttonwood 432 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$243

Firethorn 632 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$124

Doveplum 621 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$151

Chinaberry 413 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$226

Chinaberry 953 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$156

Buttonwood 477 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$243

Large Modernized Home a Short Walk to Beach

Siesta Key house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 17 minutes

Match: Private outdoor pool (heated)

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Price per night from

$398

Palm Oasis - Relax in Comfort - 1 rental per calendar month

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 10

“Beautiful home for a quiet -relaxing getaway!” Fantastic location! House had all you could ever need and the space was perfect! The only downside was not being able to maximize the outside into the evening. Our first full day it had rained but it was humid! We spent the entire day shopping and dining out. We returned around 10:30pm & the rain stopped so we took full advantage of the outside, which is just as lovely at night. There were only 4 of us, and at 11;30 it was just my sister N law and I, no music -just taking & laughing and thats when the neighbor directly behind us loudly announced for us to "keep it down and that we were in a residential area!" The other neighbor to the right didn't hear a thing! After a long, cold, Maine winter... being outside is the #1 goal, so that was unfortunate. Virginia was very pleasant to work with.

Responds fast! avg. 42 minutes

Match: Private outdoor pool (heated)

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Price per night from

$421

Seaside Villas Unit 3BR 5241

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$188

Firethorn 513 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$129

Firethorn 613 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$129

Siesta Key Paradise! 4 Bedroom Beachfront Home

Siesta Key house

4 bedrooms / 2 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$672

Chinaberry 416 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$226

Firethorn 514 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$124

Chinaberry 414 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$226

Firethorn 611 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$129

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Lovely condo on the beach, beautiful sunsets, quiet and relaxing” We recently had another nice vacation in this first floor condo, right on the gulf. Attractive décor, well equipped kitchen, large walk-in closet, washer and dryer. Convenient parking space, looks over a lagoon behind building, great for fishing and boating in owner's kayak. Convenient to many nice restaurants and attractions. Sorry to see that the beach is smaller. Hopefully it will be rebuilt by next spring.

Match: Private outdoor pool (heated)

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Price per night from

$155

Doveplum 121 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$262

Chinaberry 921 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$156

Chinaberry 426 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$226

Firethorn 712 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$129

Our Tropical Island Home

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 26 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$133

Firethorn 812 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$129

Chinaberry 912 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$156

Chinaberry 423 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$226

Firethorn 332 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$224

Firethorn 311 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Private outdoor pool (heated)

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Price per night from

$213

Viewing 38 of 341
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