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 Beach Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
1223 rentals in Siesta Key.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
FALL DISCOUNTS!
IT DOESN'T GET ANY BETTER THAN THIS!  FULL FRONT VIEWS- FROM ALL LIVING AREA
It Doesn't Get Any Better Than This! 
Full Gulf Front-Spectacular views from every room
Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Beautiful lanai, with spectacular floor to ceiling views of the beach, gulf, wildlife and sunset.
An amazing sunset seen within the condo, or if you prefer on the beach.
Enjoy the quiet sunset, wonderful beach and relaxing.  Life is good!
Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tastefully decorated with a beachy look and feel!
Palm Trees and Paradise
#1 beach in the world - seconds from the condo
Newly discounted rates! Gorgeous one bedroom across from beach, near village!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection
Kitchen
Entryway
Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
Enjoy a Large Heated Pool and updated exercise room
King bed with full bath and Gulf View
4 Bedroom with Gulf View Siesta Key FL Beach Fun
Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
SAVE $200 for 7 nights May 14 or May 28!!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
2 BR, 2 Bath, Siesta Key Village Condo with Pool
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Doveplum 121 at Midnight Cove Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Save time - get the best Siesta Key rentals sent straight to your email!
Buttonwood 477 at Midnight Cove Siesta Key, FL.
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Firethorn 522 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach
Condo/Apartment
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
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Siesta Key Gulf Side~1st Floor Villa, 3 Heated Pools, Updated, Beachy Chic #100
Rental Home
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
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Newly renovated condo with premium features on Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Across The Street From #1 Beach- w/ RELAXED CANCELLATION POLICY Thru 12/31/2020
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Walk To Siesta Village And Beach/Pool & Hot Tub
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
LAST MINUTE PRICE!! BEACH OPEN!! SIESTA KEY , PRIVAT POOL !
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Pet friendly Home- Blocks from World Famous Siesta Key Beach
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Siesta Beach-January Specials
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
View World-famous Siesta Beach from Lanai! Closest Condo Complex to the Beach
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Private 4 Bedroom Single Family Coastal Home w/Pool 1 Block to Siesta Key Beach
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Super clean and Modern Townhouse, Style And Comfort, Steps From PRIVATE Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
NEW LISTING- Across From #1 Beach- w/ RELAXED CANCELLATION POLICY Thru 12/31/20
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
An intercoastal delight with beach access Sept to October 2020 $89 per night
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Sit Back And Watch The Parade Of Boats From Your Luxurious Condo!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Large canal house, 5BR with Heated pool
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
☀️�️ LUX CONDO w/ PRIVATE HEATED POOL * SIESTA BEACH ☀️�️
Condo/Apartment
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
LuLu's Loggerhead - Walk to Siesta Key Beach. In Village, Heated Pool, WiFi, Upd
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Newly Renovated Home on Canal, New Pool, Steps from Siesta Key Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
NEARLY BEACHFRONT-PRIVATE Heated Pool and Spa with Covered Pool Bar and Patio
Rental Home
6 bedrooms
7 bathrooms
Sleeps 18
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
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
BEST HOUSE ON SIESTA - Sleeps 24+ - Heated Private Pool w/ Slide, Spa, Gratto,
Rental Home
8 bedrooms
8 bathrooms
Sleeps 24
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Siesta Key Jamaica Royale 71 Beachside
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Perfectly Remodeled Townhome, Steps From the Private Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Siesta Key Getaway!!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Top Location on Siesta Key! Private Gate into Village! Three Private Patios!
Rental Home
3 bedrooms
2 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
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
CHATEAU du SOLEIL 10% DISCOUNT Dec 5-19
Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
BEAUTIFUL & IMPECCABLY MAINTAINED BEACHFRONT CONDO ON USA’S #1 SIESTA KEY BEACH!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Clean and Beautiful Condo with Private Beach in Beautiful Siesta Key #1 Beaches
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
LuLu's Leatherback Walk to Beach & Village, Heated Pool, WiFi, Barbecue Station,
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
123456
Siesta Key Vacation Rentals
Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.
More
Siesta Key Vacation Rentals
Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.
Lions, Tigers & Circuses
When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.
Gardens & Aquariums
Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.
Locomotives & Science
Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theater, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.
History & Baseball
From your money-saving Siesta Bay vacation rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.