We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Siesta Key Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
903 rentals in Siesta Key.
Sort by:
Tripadvisor Sort
Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
7 Minute Walk to Siesta Key’s Crescent Beach, WiFi, Updated, Patio w/ BBQ, Heate
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beach Walk Townhouse
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bright & Beachy - Steps to the Water!
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Sit Back And Watch The Parade Of Boats From Your Luxurious Condo!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Jamaica Royale
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Location 1 Bdrm Cottage 1 Block from Beach and 2 Blocks from Siesta Village
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Siesta Key rentals sent straight to your email!
New remodel. Steps to Siesta Beach! Poolside,1st flr. Near Siesta Village- Save!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Direct Gulf-Front / End Unit Fisherman's Cove A201
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Excelsior- 102 G-great Gulf side location!- 1 WEEK MIN RENTAL
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private Beach on Siesta Key, Bay Sunrises, Heated Pools/Hot tub, Tennis, Fitness
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beach Road - Tropea
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beachfront Getaway in Siesta Key
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
A Siesta Tropical Retreat - Island Pool Oasis in the Village & mins to #1 beach
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
4 Bedroom with Gulf View Siesta Key FL Beach Fun
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Siesta Beachside Bliss !
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Island House Beach Resort V4
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Peaceful Haven on Siesta Key with Beach Access
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
2 BR, 2 Bath, Siesta Key Village Condo with Pool
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Firethorn 320 at Midnight Cove Siesta Key, FL.
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
LAST MINUTE PRICE!! BEACH OPEN!! SIESTA KEY , PRIVAT POOL !
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Shells Villa - Next to Beach & Village
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Incredible beach view!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly renovated condo with premium features on Siesta Key
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
View World-famous Siesta Beach from Lanai! Closest Condo Complex to the Beach
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private 4 Bedroom Single Family Coastal Home w/Pool 1 Block to Siesta Key Beach
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Siesta Key, beach front condo on America's #1 Beach! 2 BR, 2 Bath, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Pet friendly Home- Blocks from World Famous Siesta Key Beach
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Top Rated Gulf Side, Steps from Beach, Great Amenities 2 pools, tennis, hot tub
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
BEST HOUSE ON SIESTA - Sleeps 24+ - Heated Private Pool w/ Slide, Spa, Gratto,
8 bedrooms
8 bathrooms
Sleeps 24
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
CHATEAU du SOLEIL 10% DISCOUNT Dec 5-19
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Walking distance to THE WORLD FAMOUS SIESTA KEY BEACH
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
* Special Nov 28 -Dec 12th only $150 per night * On Beach Ocean front on beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Siesta Beach is only a half a block! Sleeps 6-8
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
An intercoastal delight with beach access Sept to October 2020 $89 per night
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
AMAZING BEACH COTTAGE - Sleeps 8 in Beds. Less than 1 Block to Beach
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Siesta Key private beach access
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
BEAUTIFUL & IMPECCABLY MAINTAINED BEACHFRONT CONDO ON USA’S #1 SIESTA KEY BEACH!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
NEARLY BEACHFRONT-PRIVATE Heated Pool and Spa with Covered Pool Bar and Patio
6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly Renovated Home on Canal, New Pool, Steps from Siesta Key Beach
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Couple's Fun Getaway, Quick to Village, Easy to Beach! Super Location on key!
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PreviousNext
123456