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 Cheap 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
Neighborhood
985 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
WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Siesta Key - 2bdrm on the beach - amazing views!!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa
5 bedrooms
4 bathrooms
Sleeps 13
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
Fantastic Beachfront Condo, at Surf & Racquet Resort on Siesta Key Beach
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Palm Oasis - Relax in Comfort - 1 rental per calendar month
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Siesta Key Old Florida Cottage, Great Location at a Great Price
1 bedroom
1 bathroom
Sleeps 2
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
# 1 beach in USA SIESTA KEY Gulf side 2 Bed 2 Bath at Jamaica Royale #104!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Save time - get the best Siesta Key rentals sent straight to your email!
Island House Beach Resort V22
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Luxury Romantic Oceanfront Siesta Beach Condo #304
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Siesta Key Beachfront Condo with Gulf View!
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*
2 bedrooms
2 bathrooms
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
GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Top Floor Oceanfront View Of The #1 Beach In The USA! - Beautiful Decor!
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
1 Bedroom/ 1 Bath Condo Steps From Siesta Key Sand with Pool Access-Gulf Holiday
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Island House Beach Resort 15N
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Newly Listed... NEW Decor by Jan 10th 2021! Walk to SK Beach, 2 Heated Pools, W
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Island House Beach Resort 8N
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Siesta Palms by the Beach - Sea Spray #123
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Super Cute, Super Clean Large One Bedroom - Fully Remodeled!
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Steps From Siesta Key Beach! 1BR w/ Heated Pool
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Siesta Key Vacation Townhouse directly across the street from #1 Beach in the US
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tropical bungalow steps from the baby powder sand of Siesta Beach and Village
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort V27
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Ringling Bungalow - Lagoon View
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Siesta Beach House - 311 / Beach Cove
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
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
2 Bed/2 Bath Condo Resort View on Siesta Key Beach
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
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
Peaceful Haven on Siesta Key with Beach Access
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Sandy Toes Town Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Rent Siesta Now: A Shore Thing!
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Private 2Bed/2Bath Siesta Oasis w/ Direct Water View, Near Beach and Bay
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Siesta Beach House #211 Beautiful Updated Unit
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Watch Sunsets From Your Lanai ON THE BEACH plus FREE Boat Docks!
2 bedrooms
2 bathrooms
Sleeps 6
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
Aloha Kai - 2 beautful unit and close to pool!
2 bedrooms
2 bathrooms
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
Crystal Sands Unit 308 Siesta Key, Florida
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Seaside Villas Unit 3BR 5241
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
PreviousNext
12345620
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.