Holiday Condos in Siesta Key

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2,332 Holiday homes

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 5

24

Responds fast! avg. 3 hours 33 minutes

from £136 / night

£873 - £1,479 / week

600 ft. to Shell Beach, Pool/Spa, Fire Pit, New & Custom Nantucket Style Home,

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

from £219 / night

£1,527 - £3,084 / week

Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

5

from £81 / night

£567 - £1,135 / week

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

5

Responds fast! avg. 3 hours 6 minutes

from £100 / night

£697 / week

Brand New, Walk to Beach, Wifi, Water view from patio, Heated Pool, On Trolley L

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

from £94 / night

£617 - £1,332 / week

Walk to the beach from this adorable condo. Beachside. Perfect location.

Siesta Key house

1 bedroom / 1 bathroom / sleeps 2

5

Responds fast! avg. 49 minutes

from £84 / night

£1,374 / week

"Cottage by the Sea" 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

from £130 / night

£910 / week

Across the street from Siesta Key Beach, Gulf View, Pool, Tennis, Parking, Balco

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 minutes

from £193 / night

£987 - £1,873 / week

Sandy Toes Siesta Key Florida (6796)

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

23

Responds fast! avg. 1 hour 2 minutes

from £349 / night

£1,832 - £2,094 / week

Jamaica Royale #92 on the #1 Beach in the USA!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

4

Responds fast! avg. 1 hour 35 minutes

from £219 / night

£1,533 / week

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 7

16

Responds fast! avg. 3 hours 33 minutes

from £174 / night

£1,156 - £1,832 / week

2 Bedroom Beachfront Home on Siesta Beach!! Directly on the beach!! 47 Beach Rd

Siesta Key townhouse

2 bedrooms / 2 bathrooms / sleeps 4

from £183 / night

£1,280 / week

3 Bedroom/ 2 Bath unit across from Siesta Key Beach Access.- Islamorada

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 8

from £157 / night

£1,094 / week

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

10

Responds fast! avg. 3 hours 8 minutes

from £187 / night

£1,305 - £2,011 / week

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

from £88 / night

£611 / week

Best Deals on Siesta Key

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

36

from £79 / night

£524 - £829 / week

Top Floor End Unit Directly Across the Street from Siesta Key public beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

3

from £112 / night

£786 / week

Beachfront Getaway in Siesta Key

Siesta Key townhouse

1 bedroom / 1 bathroom / sleeps 4

23

Responds fast! avg. 2 hours 42 minutes

from £164 / night

£1,148 / week

Walk to Siesta Key Beach, Wifi Included in this Private Villa, Heated Pool & Com

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

from £165 / night

£690 - £1,222 / week

Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 6

2

Responds fast! avg. 3 minutes

from £194 / night

£1,402 - £1,634 / week

Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

17

Responds fast! avg. 3 hours 3 minutes

from £139 / night

£973 - £2,081 / week

LJ's "Rustic Cottage"-- 2 Bedroom/ 2 Bath Steps From The Sand With Pool Access!!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 8

1

from £139 / night

£971 / week

Complex on the Bay, Walk to Beaches, Wifi, Ground Floor, Renovated, Enclosed Pat

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

from £94 / night

£639 - £676 / week

Jamaica Royale #100-Peaceful Gulf Side Condo

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

7

Responds fast! avg. 2 hours 34 minutes

from £148 / night

£1,032 / week

Perfect Getaway-2Bedroom/2Bath Steps from Beach with Pool Access!!- La Estrella

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

from £174 / night

£1,216 / week

Gulf Beach, Pool And Walk To Siesta Key Village

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

5

from £88 / night

£611 - £1,135 / week

Siesta Key Beach w/ Partial Gulf Views Across the Street, Renovated, Overlooks H

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

1

Responds fast! avg. 3 minutes

from £95 / night

£698 - £1,545 / week

Beautifully Renovated & Modern, Wifi, Harbor Towers, 3 bedroom with den

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

from £200 / night

£865 - £1,671 / week

5 Bedroom Beachfront Home on Siesta Beach!! 49 Beach Rd

Siesta Key house

5 bedrooms / 3 bathrooms / sleeps 10

from £515 / night

£3,603 / week

Siesta Key Condo w/Private Beach Access, Wifi Included, Heated Pool, Tennis & B

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

from £123 / night

£798 - £1,836 / week

Crescent Beach Resort, Heated Pool, Jacuzzi, Tennis, Barbeques

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

3

Responds fast! avg. 2 hours 29 minutes

from £162 / night

£1,130 - £1,776 / week

The Perfect 2Bedroom/2Bath Steps Away From Siesta Key Beach- BiancoSands

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

from £183 / night

£1,277 / week

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

33

Responds fast! avg. 1 hour 5 minutes

from £312 / night

£2,181 / week

Sea Club II

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 5

1

from £69 / night

£483 / week

Walk to Siesta Beach, Heated Pool, Wifi, Fido friendly, Renovated Ground Floor U

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

from £113 / night

£645 - £1,268 / week

goldeneye luxury private family plantation house

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

from £243 / night

£1,702 / week

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

7

Responds fast! avg. 1 hour 43 minutes

from £109 / night

£764 / week

Chinaberry 942 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

1

from £119 / night

£835 - £1,600 / week

Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

1

Responds fast! avg. 3 minutes

from £139 / night

£1,571 / week

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

4

Responds fast! avg. 2 hours 5 minutes

from £124 / night

£868 / week

Viewing 40 of 2,332
rentals in Siesta Key