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! Welcome to Just Breathe. This ultimate Siesta Key beach house getaway has all you need and more. Situated on a peaceful canal with a private pool and dock that offers plenty of s
An Ascendia Property! This spacious, fully-updated 3 bedroom/bathroom pool house is big enough for you, your friends, and your family...and it is ON A CANAL- you might be able to see dolphins and mana
UNFURNISHED, SMALL PET FRIENDLY HOME. 3 bedrooms, 2 baths, 2 car garage, inside laundry, NO CARPET, spacious split floor plan with a family room and screened in lanai. Quite Cul-de-Sac neighborhood, g
WOW! Enjoy a little slice of heaven on the World Famous Siesta Key! This beautifully renovated turnkey 3 bedroom 2 bath, heated pool home, is just a short distance to the #1 rated beaches and the quai
Adorable home for rent on Siesta Key. Less than one mile walk to the beach! Open floorplan with tasteful modern furnishings and huge back porch with no rear neighbors all on a quiet little circle neig
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
1/65
$16,000/mo
3 beds3 baths1,620 sq ft
5238 Winding Way, Sarasota, FL 34242
Parking • A/C • Dishwasher
See new homes first
Save your filters and get updated when new homes hit the market.
Welcome to this stunning, turnkey furnished home located in the highly sought-after area just off University Parkway. This modern and stylish home is only two years old and offers all the comforts and
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
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
Large end-unit townhouse located in Promenade East at Palmer Ranch is now available. The 1758 sq. ft. home features 3 bedrooms and 2.5 bathrooms. In this two-story, larger than the inside units, all c
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
SIESTA KEY, Adorable 2/2 SFH with a private saltwater pool for the wonderful beach getaway. This house is located near by the award winning Siesta Key Beach(5 minutes away) and Siesta Village((two min
An Ascendia Group Property! **Listing reflects off season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $8,600/month), (MAY - DEC - off season: $4,500/month). Available beginn
Welcome to your luxurious retreat in the highly coveted Village Walk community. Nestled within the confines of a gated enclave, this meticulously maintained three-bedroom, three-bathroom townhome offe
An Ascendia Property! **Listing reflects peak season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $8,500/month), (MAY - DEC - off season: $5,500/month). The rental rate in th
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
Available with a start date of January 1 - 2025 perfect for your winter escape 2025....Exceptional 3 bedroom, 2 bath home with office full of vibrant colors offering a cheerful coastal decor located i
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
An Ascendia Property! Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing! Picture this: you roll out of bed and grab your coffee, take two s
Amazing POOL Home near Siesta Key Beach - available for MONTH-TO-MONTH Rentals, SEASONAL RENTALS, or ANNUAL RENTAL!Looking for the absolute PERFECT turnkey beach vacation location WITH YOUR OWN PRIVAT
Welcome to Three Palms Bungalow! Located in the heartof downtown Sarasota in Historic Laurel Park, this perfectly restored 2 bedroom, 1 bath vintage cottage has all the charm. The stained glasswindows
A RARE & EXPANSIVE WATERFRONT SARASOTA PROPERTY ~ ANNUAL RESIDENTIAL RENTAL ~ UNFURNISHED ~ 1.6 ACRES ~ CENTRAL LOCATION ~ PRIVATE ~ RV & BOAT PARKING ~ NO HOA ~ SEE PHOTOS & VIRTUAL TOUR FOR A DETAI
Available now! Rented for the 2025 winter season. This 3 bedroom + den pool home with high ceilings and open concept floor plan lends itself to family gatherings and entertaining. You will love the mo
Designer furnished, cozy, stylish Vintage Florida home on Phillippi Creek. See an abundance of wildlife, including birds, dolphins and manatees right at your waterfront deck! Kayak and Paddleboard to
Move in Ready! Fully furnished home(turn-key), This beautiful home available for rent in a highly desired community in a friendly neighborhood! 3 bedrooms with 1 bonus/den, 3 full bathrooms, and scree
Enjoy Life at this SARASOTA for POOL HOME FOR LEASE ready for you to move-in and RELAX. This Lovely FURNISHED HOME is located in a residential neighborhood on Philippi Creek that includes the use of a
This is a two bedroom one bath home located near Siesta Beach in the Phillippi Crest neighborhood. The home features a large carport and ceramic tile through the open floor plan. The home is located i
Come visit this quiet OASIS in Phillippi Gardens. This home has been beautifully updated and is nestled back into a private neighborhood that is minutes from the world famous SIESTA KEY BEACHES. This
**BEAUTIFUL PROPERTY, FULLY FURNISHED available APRIL 2024 UNTIL THE END OF SEPTEMBER 2024.** Open floor plan with volume ceilings plus outdoor screened in lanai with retractable awning. Your outdoor
Welcome to Edgewater Bungalow! This stunning 3-bedroom, 2-bathroom single-level home is just 4 miles from the world-renowned Siesta Key Beach and 5 miles from Downtown Sarasota! Siesta Key, in gorgeou
Looking for the perfect rental property? Look no further than this remodeled Waterfront canal front 3 bed 3 1/2 bathhome with bay access! Situated in a large fenced lot, this stunning luxurious home b
Experience the best of Sarasota living in our fully renovated 3-bedroom, 2-bathroom home, just 10 minutes from the stunning Siesta Key beach. This annual rental offers modern comforts and easy access
Over 55 community;Great Little Oasis with all the benefits Florida has to offer. 15 minutes from Beaches, downtown, restaurants, shopping and much more. This two bedroom 1 bath with a sizable living r
Beautifully updated 3 bedroom, 2 bath Sarasota home - 4 miles from award winning Siesta Key Beach and close to active downtown Sarasota. Enjoy the spacious living space, multiple sitting areas with pa
Lovely 3 bed 2 bath home with pool available now. It is currently furnished as it had previously been used for short term rental. Now can be rented long term. Tenant has the option to rent the home fu
Fully furnished short-term rental, turnkey. Quiet paradise with private backyard and pool, close to everything, beaches, restaurants, bars, museums, everything! Embrace the quintessential Florida life
Welcome to your next home in vibrant Sarasota, FL! This spacious and beautifully updated 4-bedroom, 3-bathroom residence is designed for comfort and modern living. With a generous open floor plan and
Based on information submitted to the MLS GRID as of Sun Jun 02 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.