Welcome to our luxurious three-story holiday residence and boating home, or as we like to call it... Your Personal Resort! This stunning home is the perfect place where you and your loved ones can get
There is nothing like this on Siesta Key available for rental on short term basis. This is truly a beach house, immaculate and beautiful! While there are many gulf front condos, and single family home
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!!!
Bask in the sunshine and sit in the pristine crystal white sands on Crescent Beach, rated #1 in the country by Dr. Beach. This beachfront sanctuary offers a fitness center, heated pool, outdoor grotto
Serenity at its finest! If luxury is calling, come indulge at the Beach House Residences for your ultimate beach vacation experiences. A place to escape and rediscover you. Renew your senses, inspire
Exceptional Siesta Key Oasis with 6 Bedrooms, Deeded Beach Access, and Luxury Amenities!Nestled in the coveted Tortoise Estates, this 6-bedroom, 4-bathroom haven boasts an array of enticing features.
Amazing opportunity, to find a rental like this hidden gem! Live your best life with the island lifestyle and enjoy the best of both worlds with the beach and boating. DEEP SAILBOAT WATER BOATING or t
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$18,000/mo
5 beds4.5 baths3,714 sq ft
5719 Riegels Point Rd, Sarasota, FL 34242
Pets welcome • Parking • A/C
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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 Property! **Listing reflects off season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $18,000/month), (MAY - DEC - off season: $15,000/month). Available beginning
Welcome to Caribbean Dream! Discover the epitome of island-style luxury as you step into this stunning retreat, nestled just moments away from the pristine shores of Siesta Key Beach. Renowned for its
THE SEA BREEZE: Exclusive seasonal rental for the discerning taste. This beautiful 3 bedroom, 3 1/2 bath residence has magnificent views of Sarasota Bay and the Gulf of Mexico/ Premium space in this l
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
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
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
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$12,500/mo
3 beds2 baths1,645 sq ft
1341 Siesta Bayside Dr Unit 1341B, Sarasota, FL 34242
PENTHOUSE Water Views From Every Room!AVAILABLE April 8, 2024-December 15, 2024.4/8/2024-12/14/2024- $12,000Contact agent about nightly rate breakdown!
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$12,000/mo
3 beds3.5 baths3,524 sq ft
1308 Old Stickney Point Rd Unit WP3, 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
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
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$12,000/mo
3 beds2 baths1,495 sq ft
1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
An Ascendia Property! "**Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** This charming home offers a delightful coastal retreat on Sie
2025 DEC/JANUARY WINTER RENTAL - S0RRY, FEB AND MARCH ARE RENTED. 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 Cl
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
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$11,000/mo
3 beds2 baths1,495 sq ft
1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
Discover the epitome of luxury living in this stunning, custom-designed Italian villa, nestled in the serene Tortoise Estates. This exquisite four-bedroom, three-bathroom residence offers direct deede
SIESTA KEY ANNUAL OR SEASONAL (2024) SINGLE FAMILY POOL HOME AVAILABLE FOR LEASE! Enjoy incredible bay views across the water to Bird Key and downtown Sarasota from this 3 bedroom, 2 bath renovated h
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
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
Open April 2025 and 2024 off-season months July 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 de
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
MONTHLY VACATION RENTAL. Introducing our BEAUTIFUL NEW LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need
Off-season special August 1 to November 1 at $10,000 per month. Season Rent $20,000-$25,000 per month. OPEN WATER, FULL BAY VIEW. From the moment you pull into the circular drive and enter through the
NOW AVAILABLE FOR SEASON 2025 AND ALL OFF-SEASON MONTHS! Absolutely adorable key west style cottage located on Siesta Key and lies directly on Little Sarasota Bay. This 2 story "Beach Cottage" has 3 b
An Ascendia Property! Welcome to "The Dove" on Siesta Key! With 4 bedrooms and 3 bathrooms, this spacious property can comfortably accommodate up to 10 guests, making it an ideal choice for your next
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
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$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
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$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
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$9,500/mo
3 beds2 baths1,835 sq ft
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
Based on information submitted to the MLS GRID as of Sun Jun 09 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.