6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!
AVAILABLE FOR 2025 SEASON!! Enjoy this beautiful 3-bedroom and 3-bathroom remodeled home on Siesta key, named the #1 Beach in the country! Brand new pool set to be completed fall 2023. We are LESS TH
An Ascendia Group Property! Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sand
An Ascendia Property! An ultimate water lover's dream home on Siesta Key (Sleeps 8) this property truly has it all. Kayak or paddle board right from your backyard. Fish from your private dock, and gri
AVAILABLE 2025 SEASON... 90 DAY MIN.AVAILABLE APR.-DEC. 2024...30 DAY MIN.Fabulous pool home located in one of Siesta Keys most sought after areas. Interior is nicely furnished. Take a late night swim
2025 WINTER RENTAL at the Premiere Club at Gulf and Bay. This 2 bed/2 bath unit has a vast, unincumbered view of the famous Siesta Beach! Gulf and Bay Club is a luxury community sitting on 32 acres of
An Ascendia Property! **WEEKLY STAYS AVAILABLE! Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** Take some time to get away from it all
Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a shortwalk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a
An Ascendia Property! Paradise awaits in this UPDATED canal front home on Siesta Key. This 3-bedroom 2-bathroom POOL home features an open concept with tile floors, wood kitchen cabinets, granite coun
Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distanc
$12,500/mo
3 beds2 baths1,645 sq ft
1341 Siesta Bayside Dr Unit 1341B, Sarasota, FL 34242
LOCATION, LOCATION, LOCATION!!! Stunning large luxury condo located in the sought after community of Summer Cove on Siesta Key. This corner unit, light and bright property has been meticulously profes
Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bat
Open from December 15th to January 15th 2022. Rented from January 15th to March 31, 2023. Available all of April~ Extraordinary Key West style single family pool home is a 3 Bedroom 3.5 Bath positione
Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for
Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distanc
$12,000/mo
3 beds2 baths1,495 sq ft
1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinn
$11,000/mo
3 beds2 baths1,495 sq ft
1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
An Ascendia Property! Spectacular is an understatement when describing this updated Siesta Key CANAL FRONT POOL HOME. Once you step inside you'll notice an open-airy floor plan, beautifully decorated
Available off-season May through October. Located on Palm Island on Siesta Key, this whimsical 3 bedroom, 3 bath bungalow will amaze and delight your senses! The attention to detail and quality of fin
LOCATION, LOCATION, LOCATION!! Absolutely beautiful TURNKEY furnished townhouse is available to rent in the sought after Siesta Key community of Tiffany Sands. This three story townhouse has three bed
An Ascendia Property! **AVAILABLE FOR WEEKLY RENTALS! Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** It's all about the beach and the
Welcome to our stunning vacation rental condo in Siesta Key, Florida! This magnificent 3 bedroom, 2 and a half bath condo offers the perfect tropical escape. With its prime location on the 8th floor o
SHORT TERM RENTALThis 2 bedroom condo offers bay views, is an end unit, has a light and bright interior and is just steps from the Bayfront pool! There is a sleeper sofa in the living room to accommod
Yes!!! Available March 1st through March 31 2024 - Enjoy Full Gulf of Mexico Views for the entire month in Paradise of Siesta KeyEnjoy panoramic views of the #1 beach in the USA, Siesta Key! This beau
$10,000/mo
2 beds2 baths1,337 sq ft
5740 Midnight Pass Rd Unit 303F, Siesta Key, FL 34242
Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park yo
$9,900/mo
2 beds2 baths1,280 sq ft
1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed re
$9,500/mo
3 beds2 baths1,835 sq ft
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
Welcome to your elevated sanctuary in paradise - a second-floor two-bedroom condo at Gulf & Bay Bayside on the enchanting Siesta Key, Florida. Upon entering, you're immediately greeted by an open-conc
$9,500/mo
2 beds2 baths1,280 sq ft
1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
This fabulous two bedroom features the primary bedroom with a King bed and the guest with a queen bed. The spacious living area opens onto a tiled lanai surrounded with sliding windows/doors that can
$9,300/mo
2 beds2 baths959 sq ft
1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242
This spacious, private and light-colored 2-bedroom/2-bathroom end unit has a lanai that overlooks a lake with frequent bird sightings. Walk right out to an inland waterway and fishing dock. A large, h
$9,300/mo
2 beds2 baths1,280 sq ft
1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access - 5 minute walk. Tile floors throughout and completely re-decorated and furnished with man
$9,300/mo
3 beds2 baths1,280 sq ft
1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
Deeded Walking Access Directly to the Beach!New on the rental program - Beautifully updated 2-bedroom near the pool, tennis courts and path to the beach! Please be one of our first Guests!The moment y
$9,300/mo
2 beds2 baths1,280 sq ft
1269 Siesta Bayside Dr Unit 1269C, Sarasota, FL 34242
Relax in this spacious two bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private, walking b
$9,300/mo
2 beds2 baths1,130 sq ft
1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
Unwind in style and comfort in this expansive two-bedroom, two-bathroom vacation retreat, perfectly nestled in the prestigious Gulf and Bay - Bayside community on Siesta Key. This condominium is thoug
$9,300/mo
2 beds2 baths1,280 sq ft
1239 Siesta Bayside Dr Unit 1239C, Sarasota, FL 34242
Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom vacation rental condo. The condo offers a relaxing lake, pool and tennis court
$9,300/mo
2 beds2 baths1,280 sq ft
1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
Want to be able to walk three blocks to Siesta Key beach? Vacation here and you can! This private 3 bedroom 2 1/2 bathroom pool home is warm and inviting and lushly landscaped. There is large screen
Welcome to this stunning second-level condo nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this metic
$8,900/mo
3 beds2 baths1,645 sq ft
1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
An Ascendia Property! **WEEKLY RENTALS! Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** Your vacation starts here... with this delight
Welcome to your very own slice of Siesta Key paradise! This charming single-story Florida beach home offers the quintessential island experience, and it's now available for monthly rentals in beautifu
An Ascendia Group Property! Nestled under a stunning Banyan tree this "original" Siesta Key cottage combines Old Florida charm with modern updates with TONS of character. Set amongst a lush private y
**BOOKED UNTIL THE END OF MARCH 2024 ** BEACHFRONT! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor 2 Bedroom/ 2 Bath luxury condo. Full Gulf views from living room/dinin
Based on information submitted to the MLS GRID as of Mon Apr 29 2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.