Siesta Key, FL Homes for Rent with Private Pool

Experience Siesta Key living at 5585 Contento Dr; a furnished 4 bedroom 3 bath pool home that is available immediately for rent. This home sits at the end of a quiet cult de sac in the front and offers beautiful canal views, a wooden boat dock, and heated pool in the back. This split floor plan home boasts 1,921 square feet under air and a two car garage that includes a full sized washer and

Joe Failla PREMIER SOTHEBYS INTL REALTY

Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel

Robert Bevington SHOWTIME REALTY

Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated, this home

Robert Bevington SHOWTIME REALTY

SIESTA KEY, Sarasota, Single Family Pool Home….Well-positioned for convenience and natural attractions . . . and dinners are breezy on your patio! The advantages of this appealing home in the Siesta area of Siesta Key become apparent while you are still walking the perimeter. The clear blue pool and the patio are a perfect pairing of amenities, supporting a variety of social activities and

Jane Hunter JENNETTE PROPERTIES INC

Availability June 1st for Annual Lease. Welcome to your tropical escape on Siesta Key! This serene 3-bedroom, 2-bath annual rental offers a wide open floor plan with vaulted ceilings, split bedrooms, and a spacious 2-car garage. The stone-accented great room flows effortlessly into the kitchen with a unique breakfast bar, all overlooking the screened-in pool and lush tropical landscaping. Recent

Anthony Dalesandro BRIGHT REALTY

Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street, this home has so much to offer. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with

Chrissie Cummings JENNETTE PROPERTIES INC

AVAILABLE October, November 2025! Currently booked through September 2025. Also booked December - March 2026. 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 quaint shops and restaurants in the downtown village. Whether it’s our million-dollar

Scott Nold TNG PROPERTY MANAGEMENT

You will Never Want to Leave this 4-bedroom house on Siesta Key! Mid-Century Modern, 4 bedroom home with saltwater, heated Pool with canal views. Located within a 6 minute bike ride to Siesta Key's Beach Access #5 and walking distance to everything that Siesta Key Village has to offer. This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, "Sarasota School of Architecture style"

Kelly Anderson RE/MAX ALLIANCE GROUP

scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort.??? Just a 3-Min Drive to Siesta Beach??? 10 Minutes to Crescent Beach????? 13-Min Walk to a Local BeachDiscover the best of Sarasota with us!

Valerie McInerney LPT REALTY, LLC

It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

Beth Dilley ASCENDIA REAL ESTATE

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 grill your fresh catch poolside while your family splashes in the crystal clear waters of the oversized pool. Watch colorful sunsets while sipping your favorite beverage in the bubbling outdoor spa. This expansive

Beth Dilley ASCENDIA REAL ESTATE

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 to reflect a modern beach-style home! Enjoy the master bedroom with BEAUTIFUL VIEWS of the canal and your very own access to the refreshing POOL and SPACIOUS PATIO! The additional two bedrooms are roomy and private with

Beth Dilley ASCENDIA REAL ESTATE

Check out this COMPLETELY REMODELED canal-front pool home on Siesta Key! Picture this: you roll out of bed and grab your coffee, take two steps out of the sliding glass doors, and enjoy it by the saltwater pool. After your coffee, take your morning swim. Then take another 10 steps, or so, and catch some significant fish in the canal which happens to be in your backyard. Chances are that an

Beth Dilley ASCENDIA REAL ESTATE

Welcome to Surf’s Up, a modern coastal beach inspired home, where you will enjoy and marvel at the crystal-clear waters of the Gulf of Mexico. This home was purchased, designed, equipped, and furnished for families to experience the ultimate vacation home. Located just 10 homes from the most beautiful beach in the United States, Siesta Key! This newly remodeled home with brand new furnishings

Beth Dilley ASCENDIA REAL ESTATE

AVAILABLE MAY-JUNE-JULY and August 2025Beautiful house on Siesta Key with private pool (not heated) and generous space. 15 min walk to the beach!This charming 3-bedroom, 2-bathroom private home is located in discreet residential neighborhood, on the beautiful Siesta Key island.It offers a private pool, plenty of parking and can accommodate up to 6 guests!This is a well maintained

Sandrine Maquet LPT REALTY, LLC

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 yard this adorable 3 bedroom 2 bathroom POOL home is the perfect place to spend time relaxing on Siesta Key. Enjoy an ideal location on a quiet street near Siesta Village, with numerous beach access points, shopping, dining, and

Beth Dilley ASCENDIA REAL ESTATE

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 counter tops and stainless appliances. This property is PERFECT for your next family gathering and easily accommodates up to 6 guests in one king, one queen, one full and one twin bed. One of the master bedrooms is on the

Beth Dilley ASCENDIA REAL ESTATE

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!!!TROPICAL PARADISE. SIESTA KEY'S "OUTDOOR ACADEMY"!!! ONLY 1/2 MILE AWAY! One-of-a-kind enclave of Sandy Hook at USA's No 1 BEACH. A private road takes you to Elevated living area with entry

Joseph Russo COURTYARD MODERN

Booked the rest of 2024 and 2025. Only available April 5th through April30th 2025 Extraordinary Key West style single family pool home is a 3 Bedroom 3.5 Bath positioned on the Grand Canal with 1 bridge to Roberts Bay. The modern, symplystic, and uncluttered interior complement the relaxed tropical setting. In the gourmet kitchen you will find a charming cast iron Elmira stove and the

Jennifer LeBlanc PRECISE REALTY CORP

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 large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car! A brand new beautiful granite topped Kitchen space opens to a family room all

Catherine Foley JENNETTE PROPERTIES, INC.