Siesta Key, FL Homes for Rent with Private Pool

This is a short term rental. Listing reflects peak season rate. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults

Beth Dilley ASCENDIA REAL ESTATE

Beach or pool today? Or perhaps you'd rather stay in and enjoy a good book on the charming porch of Villa 53 at Aloha Kai. This beautifully remodeled retreat features an updated kitchen and bath, paired perfectly with coastal-inspired furnishings that create a relaxing home away from home. The spacious bedroom offers generous closet space, ensuring comfort and convenience during your stay.

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee at LeLu Coffee Lounge. 4 bedrooms and 2.5 baths brings you back inside with a

Joseph Meszaros M&M PROPERTY MANAGEMENT GROUP

Villa 45 at Aloha Kai is a light-filled coastal retreat featuring an updated kitchen that perfectly complements its bright, beachy furnishings. Whether you prefer a refreshing swim in the Gulf of Mexico or a relaxing afternoon by the pool, the choice is yours. With a king bed and two twin beds, this villa comfortably accommodates guests, making it ideal for a family visit. The front porch and

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

C6 is a lovely unit, has been remodeled and is awaiting your arrival. It can accommodate up to 6. The spacious living room/dining room has all new furniture, including a large couch, two recliners, coffee, and end tables. In the dining area you will find a new dining table and chairs and a ceiling fan. There is also a wall-mounted 55” UHD Smart TV. The very large Master Bedroom has a king-size

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

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

Villa 2 at Aloha Kai is beautifully situated on Siesta Key, a popular barrier island along Florida’s West Coast. This family-friendly, gated resort community is nestled in the heart of Crescent Beach, which is ranked as the number one beach in the continental United States. Known for its dazzling white quartz sand and vibrant emerald-green waters, Siesta Key is among Florida’s top vacation

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Charming 3 bed/2 bath waterfront estate located on the coveted north end of Siesta Key. This parcel is one of the last of its kind, featuring 1.3 acres of prime waterfront property overlooking Cocoanut Bayou. Completely private by its original growth of lush tropical landscaping, this property is captivating for all your senses. This 1,500 sqft home was built in 1946 and will wow you from the

Joleisy Machado-Gonzales RELAX PROPERTY GROUP, LLC

Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations. Step inside to find over-sized rooms that can be utilized for entertaining or simply

Colette Jay HORIZON REALTY INTERNATIONAL

Available as a monthly rental in May, August, September, October, November and December 2026 only!Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun.

Beth Dilley ASCENDIA REAL ESTATE

If you’re searching for the perfect location for your next vacation, your search ends here!This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid

Robert Bevington SHOWTIME REALTY

Enjoy a relaxing getaway in Villa 3 at Aloha Kai, a cozy beach villa beautifully decorated with casual coastal charm. The screened porch provides the perfect spot for morning coffee, unwinding with a good book, or entertaining guests in the evening with a meal or cocktail. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Welcome to your dream escape on Siesta Key—a completely reimagined coastal retreat designed to make every moment unforgettable.Tucked away on a quiet stretch of Avenida de Parasido, this stunning 3-bedroom, 2-bath home has been fully remodeled from top to bottom with brand-new, designer furnishings. Everything is fresh, pristine, and waiting, be among the very first to experience it.Step

Beth Dilley ASCENDIA REAL ESTATE

Villa 1 at Aloha Kai is ideally situated on Siesta Key, a popular barrier island along Florida’s West Coast. Nestled within the family-friendly, gated resort community of Aloha Kai, it lies in the heart of Crescent Beach—ranked the number one beach in the continental United States. Renowned for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Paradise awaits you at Siesta Key! Experience the beauty of the #1 Beach in the USA with this gorgeous 2 bedroom 2 bath stunning beach view condo overlooking the pool. This beautiful condo is just steps from the pool and Direct Beach Access. Amenities for the complex include: 2 fitness centers, 2 heated pools, a fishing pier, 2 clubhouses, pickle-ball and tennis courts. You will enjoy hopping on

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

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. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

Chrissie Cummings JENNETTE PROPERTIES INC

Listing reflects peak season rate. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a bright, coastal-styled haven designed for relaxation and comfort. The spacious primary

Beth Dilley ASCENDIA REAL ESTATE

This property is a 30 night minimum.This 2 bedroom, 2 bath is a first floor garden condo on the bay side of Midnight Pass.The master bedroom has a King bed, a ceiling fan, a 32 inch smart TV, and windows for natural light. The master bathroom has updated granite counters and a walk-in shower with a sliding glass door and a removable shower head.The guest bedroom has a king bed, a

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

AVAILABLE after June 1, 2026! Enjoy your own slice of paradise on World Famous Siesta Key! This beautifully renovated turnkey 3-bedroom, 2-bath heated pool home is just a short distance from the #1-rated beaches and the charming shops and restaurants of Siesta Key Village. Whether you're here for million-dollar sunsets, endless watersports, the famous Sunday Drum Circle, or simply peaceful days

Scott Nold TNG REAL ESTATE

We welcome you to stay in our updated oceanfront condo on Siesta Key Crescent Beach - the best beach in Florida! Our spacious 2 bed/2 bath oceanfront home is 1080 square feet with an ocean view that cannot be beat! Unit #206 is part of the Casa Blanca Vacation Beach Resort, and the crystal white sand is steps away! Remodeled in 2023, fully equipped kitchen with quiet dishwasher, spacious living

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

This is a short term rental. Listing reflects off season rate. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates throughout,

Beth Dilley ASCENDIA REAL ESTATE

Newly remodeled and furnished “Bougie beach bungalow” on Siesta Key Island. This Condo will “wow” you from the first moment you enter. Just say Alexa turn lights on and your command will be answered. This condo is on the first floor and it’s just a few minutes walk from the siesta key public beach access. The community is very welcoming to all guest and has a heated pool year-round and also many

Stephanie Fox EXP REALTY LLC

This is a short term rental. Listing reflects off season rate. New to the rental market! Whether you’re seeking a relaxing beach escape or an adventure-filled vacation, Island Retreat offers the perfect home base. Its prime location, luxurious amenities, and proximity to both the beach and Siesta Key Village make it an exceptional choice for creating unforgettable memories. Featuring 5

Beth Dilley ASCENDIA REAL ESTATE

Stunning 2BR/2BA Villa on Crescent Beach – Siesta Key's #1 Rated Beach in the USA Welcome to your luxurious beach home away from home! This newly renovated, state-of-the-art 2-bedroom, 2-bath villa is located on the pristine sands of Crescent Beach in beautiful Siesta Key—consistently ranked the #1 beach in the USA. Step inside to discover a fully updated interior featuring: Modern kitchen with

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Your cozy getaway awaits in Siesta Key at this terrific house. With three bedrooms featuring a king, queen, and full bed, guests find plenty of space to relax. The large heated pool gives you an amazing space for relaxing after a day at the beach which is just steps away. You also have a large gazebo adjacent to the pool to get out of the sun and showcase you BBQ skills. Whether you’re unwinding

Troy Jenkins REALTY EXECUTIVES GALLERY

Villa 61 at Aloha Kai warmly welcomes you with its cheerful coastal décor, designed to help you forget your worries and simply be happy. Its casual, comfortable style will make you feel right at home, while offering the luxury of both beach and pool access—you’ll just have to decide which you prefer. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Located on Siesta Key with just a 3 minute walk to Shell Beach, this 2-story home is available NOW & FURNISHED for an ANNUAL LEASE. The kitchen flows seamlessly with an OPEN LAYOUT into the expansive living and dining areas filled with NATURAL LIGHT from the large sliding glass doors opening to the SCREENED-IN LANAI. The POOL & HOT TUB/SPA, also screened-in, are framed by lush TROPICAL

Benjamin Schwab KEYRENTER SARASOTA PROPERTY MANAGEMENT

Welcome to your perfect island getaway at 301 Avenida Madera #B, ideally located in the heart of Siesta Key—this is truly THE location! Just steps from popular spots like Village Cafe and The Hub Baja Grill, and only a short walk to the world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of comfort and coastal charm. Inside, you’ll find a bright

Robert Bevington SHOWTIME REALTY

FULLY FURNISHED rental available in Siesta Key, close to the beach and walking distance to Siesta Key Village. RENTAL PRICE depends on total LENGTH OF STAY. Rent a Rare Piece of Sarasota's Architectural History on Siesta Key! Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Boasting

Daniel Petrilla PREFERRED SHORE LLC

This property is a 30 night minimum.This 2 bedroom, 1 bath is a second floor garden unit on the bay side of Midnight Pass, and is approximately 15 yards from the Intracoastal waterway.The master bedroom has a queen bed and a 40 inch TV. The master bathroom has a tub/shower combination with a sliding glass door.The guest bedroom has 2 twin beds, a ceiling fan, and window with natural

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

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

This property is a 30 night minimum. 6030 is a small garden unit, located on the Bayside of Midnight Pass Ground Floor unit. 2 bedroom, 2 bath unit . Approx. 1250 Sq. Ft. (1350 including the lanai). Bedding:Master bedroom: KingGuest Bedroom: Queen Electronics:Living room: 32 inch Flat PanelMaster Bedroom: 20 inchGuest Bedroom: 12 inch Bathrooms:Master: ShowerGuest:

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

Stunning Renovated Home for Long-Term Rent in Siesta Cove. Discover your dream coastal lifestyle in this beautifully renovated single-family home located in the exclusive neighborhood of Siesta Cove, just steps away from the acclaimed Siesta Key Beach—voted the number one beach in the United States! This elegant residence boasts 3 spacious bedrooms and 2 luxurious bathrooms, offering a high

Beth Dilley ASCENDIA REAL ESTATE

Feel the sun on your shoulders and sand between your toes when you choose the updated Villa 11 at Aloha Kai. With a spacious front porch and a back patio, this villa offers plenty of opportunities to make the most of your beach getaway. Just steps from the pool and private beach, it’s an ideal retreat for sun lovers. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha

Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

AVAILABLE for 2026... Jan., Feb and April Fantastic pool home located .4 mile from Siesta Beach access! Enjoy this completely renovated 3 bedroom / 2bath pool home in Palm Island on Siesta Key. With comfort in mind, vacation memories are waiting to be made here! All furnishings, appliances and flooring are new and decorated in coastal colors. Enjoy a morning walk to the powdery sand beach less

Brenda Cozy COLDWELL BANKER REALTY