House rentals near Siesta Beach

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

4.89 out of 5 average rating, 167 reviews

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.

5 out of 5 average rating, 110 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

4.98 out of 5 average rating, 107 reviews

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

A private heated pool is surrounded by a spacious stone patio, featuring comfortable lounge chairs. Lush greenery provides a tropical backdrop, while a charming cottage with turquoise siding is visible nearby. Soft sunlight reflects on the tranquil water, enhancing the peaceful ambiance of this outdoor area.

5 out of 5 average rating, 15 reviews

Toes In The Sand | Private Pool, Walk to Beach!

🦩Exclusive Amenities Include: • Private Heated Pool • 3 Minute Walk to Siesta Key Village • 1 Minute Walk to Siesta Key Beach • Outdoor Lounge Area • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Caddy • Gas Grill • Enhanced cleaning protocols by our CottageClean Team • Island Shuttle Transportation Available • Dog Friendly (1 dog up to 25 lbs with an additional fee)

4.97 out of 5 average rating, 258 reviews

Your private retreat near Siesta Key Beach.

Welcome to your Private Retreat! Nestled at the end of a quiet street. This distinguished property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. 3 bedroom, 2 bath, amazing heated pool home and private back yard is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes. Must be at least 25 years old

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 218 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.

4.96 out of 5 average rating, 100 reviews

2 BR House 1.6 miles from Siesta Key Beach

Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 109 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.

4.94 out of 5 average rating, 141 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want!

The exterior of the duplex presents a welcoming entrance with a covered front porch and seating. Lush greenery and small potted plants enhance the home's facade. The driveway is visible, leading to the well-maintained lawn and fenced backyard area.

4.94 out of 5 average rating, 105 reviews

1 Bed 1 bath 7 mins to the beach

This charming 1 bedroom 1 bath space has a calming coastal vibe with dedicated driveway parking, front porch, and fenced backyard. This unit is newly renovated and furnished, and is part of a duplex with a large shared backyard. It is within walking/biking distance or a short drive to grocery stores and restaurants, and 7 mins to Siesta Key - FL's #1 beach! Longboat Key, St. Armands, Turtle Beach, and Downtown are all a short drive away!

An inviting outdoor space features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned along the poolside, with lush greenery and tropical plants enhancing the landscape. A pergola provides shaded seating, creating a comfortable area for relaxation and entertainment.

4.93 out of 5 average rating, 105 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

BNB Breeze Presents: Sea Esta! Experience this stunning home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis, this home has it all! • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • E-Bikes (For Rent) • Resort-Like Back Yard w/ a Pergola, Turf + Putting Green • Pool + Beach Supplies • Fun Outdoor Swinging Dining Table

An open-concept living space features a leather sofa and a rustic coffee table. The kitchen, equipped with modern appliances, includes a gray countertop and wooden bar stools. Soft overhead lighting enhances the warm ambiance created by the wood-paneled ceiling.

5 out of 5 average rating, 355 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

Newly built and completed in 2019; this guest house is just a few minutes walk to one of the world's best beaches, Siesta Key. Your own private drive to this elegant secluded enclave is close to shopping, restaurants and all the fun Sarasota and Siesta Key offer. Tall ceilings, double pane windows, extraordinary insulation, beautiful finishes and furnishing details make this an unusually quiet and comfortable refuge.

Popular amenities for house rentals near Siesta Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene outdoor space features a sparkling pool surrounded by lush greenery. Comfortable seating is provided under a large umbrella, while decorative light fixtures enhance the ambiance. Tropical plants and well-maintained landscaping create a refreshing atmosphere for relaxation and enjoyment.

4.98 out of 5 average rating, 89 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

An outdoor dining area is presented next to a heated pool, featuring a table set with plates of food and drinks. A gas grill is nearby, and the pool is enclosed by a mesh screen. Lush greenery is visible through the enclosure, enhancing the serene environment.

5 out of 5 average rating, 7 reviews

Paradise on Prospect w/ Htd Saltwater Pool

An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.

4.99 out of 5 average rating, 93 reviews

Luxurious Private Retreat - Your Siesta Key Oasis!

A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.

5 out of 5 average rating, 12 reviews

The Palms Away

4.9 out of 5 average rating, 114 reviews

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool

A private heated pool is centered in the backyard, surrounded by palm trees and illuminated by soft outdoor lighting. A spacious lanai is visible on one side, featuring a shaded seating area. The sky shows a blend of warm sunset colors in the background.

4.9 out of 5 average rating, 29 reviews

Private Pool - Beach 100 steps, Village 5-min walk

Superhost

5 out of 5 average rating, 4 reviews

Heated Pool, Near Siesta Key Beach & Downtown

Superhost

An inviting living area features a spacious sectional sofa adorned with vibrant pillows and a cozy fireplace. Large glass doors provide natural light and views of the outdoor pool area, while a unique coffee table complements the mid-century modern design.

5 out of 5 average rating, 8 reviews

Mid-Century Modern, Pool, Mins to Siesta Key Beach

Weekly house rentals

A bright and airy living area features a sleek white sectional sofa with decorative pillows. A dark coffee table is centered in front, adorned with two gold vases. Framed art pieces are arranged on the wall, adding a touch of elegance to the space.

4.95 out of 5 average rating, 79 reviews

Siesta Key Escape-8 min to the beach,Spa,Bikes,BBQ

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

4.93 out of 5 average rating, 27 reviews

Coastal Retreat near Siesta Key Beach and Downtown

5 out of 5 average rating, 12 reviews

Home in Holmes Beach

NEW! Coconuts 106! Beach Front! Heat Pool!

A wooden sign is illuminated in red light, displaying the words 'BEACH HOUSE' prominently above the number '669.' The sign rests on a rustic base, surrounded by a sandy area, creating a welcoming entry point to the property.

5 out of 5 average rating, 9 reviews

Walk to Siesta Key Beach 100 feet!

4.88 out of 5 average rating, 85 reviews

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!

A spacious living area features a comfortable light-colored sofa complemented by a vibrant blue accent chair. The floor showcases a bold black-and-white rug, while artwork adorns the walls. A side table with a lamp is visible, creating an inviting atmosphere for relaxation.

4.91 out of 5 average rating, 54 reviews

Ben's Bungalow | 8 min to Siesta Key | Giga Wifi

A serene outdoor area features a heated saltwater pool surrounded by a screened enclosure. Two lounge chairs are positioned under an umbrella, while lush greenery adorns the perimeter, creating a calming atmosphere at sunset.

5 out of 5 average rating, 42 reviews

Walk to Siesta Village, Heated Saltwater Pool

4.93 out of 5 average rating, 28 reviews

Sarasota Pool Home| Hot-tub| 2-miles to Siesta

Private house rentals

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5 out of 5 average rating, 77 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

5 out of 5 average rating, 52 reviews

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

Home in Holmes Beach

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

5 out of 5 average rating, 7 reviews

Home in Bradenton

New! Boat Dock + Dolphins + Beaches + Hot tub!

4.97 out of 5 average rating, 70 reviews

A serene bedroom featuring a spacious bed with light bedding. Natural light pours in through two windows, illuminating the room's wooden beams and soft green paneling. A small table with a lamp and decorative items completes the inviting space.

Home in Myakka City

"Little Siesta" - Farm home near Terra Nova

A screened lanai showcases a heated pool and spa, surrounded by twinkling string lights. Lounger chairs and outdoor dining furniture are positioned nearby. A grassy area is visible beyond the pool, while a pink inflatable floats in the water, enhancing the serene outdoor setting.

4.98 out of 5 average rating, 65 reviews

Coastal Home in Sarasota-8min from Siesta Key

5 out of 5 average rating, 10 reviews

Pool house with outdoor shower, 10 minutes from SK

5 out of 5 average rating, 41 reviews

A cozy outdoor seating area features two blue chairs positioned near a glass-top table with a glowing fire feature. The background showcases serene water views, surrounded by palm trees and residential homes, under a colorful sunset sky.

Home in Holmes Beach

Heated Pool, Elevator, Dock, Waterfront, Fire Pit

5 out of 5 average rating, 87 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

Pet-friendly house rentals

Superhost

A serene outdoor space encompasses a private pool, surrounded by paved decking and lush greenery. Lounge seating and a covered dining area offer comfort. An umbrella provides shade, while a playful pink float adds a splash of color, inviting relaxation on sunny days.

5 out of 5 average rating, 3 reviews

"The Nest" Luxury 3BR, Heated Pool, Near SK Beach!

The exterior of the villa is displayed, featuring a welcoming blue-green door and two large windows framed in white. A small potted plant accents the entrance, while a pathway leads to the door, surrounded by well-maintained grass and greenery.

4.87 out of 5 average rating, 115 reviews

Charming Villa 14 mins away from Siesta Key Beach

A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.

4.93 out of 5 average rating, 106 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

4.95 out of 5 average rating, 83 reviews

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

An aerial view of a single-story home with a blue exterior and a metal roof highlights a private pool surrounded by a spacious patio. Lush landscaping and palm trees create a tropical atmosphere, while a shaded seating area under the umbrella invites relaxation.

5 out of 5 average rating, 42 reviews

Waterfront Retreat | Heated Pool & Boat Dock

A well-appointed backyard features a heated saltwater pool surrounded by elegant stone decking. Lush green artificial grass lines the pool area, enhancing the design. Comfortable lounge chairs are positioned nearby, offering a relaxing space for enjoyment under the shade of sleek umbrellas.

4.94 out of 5 average rating, 88 reviews

Private Heated Saltwater Pool & Spa 1 mi to Beach

4.89 out of 5 average rating, 9 reviews

Siesta Sands 1 Mile to Beach

A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.