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!

An inviting fire pit is surrounded by a circular stone seating area, featuring two Adirondack chairs. Decorative cushions add color to the seating. A spacious, fenced backyard is complemented by a serene evening sky with pastel hues.

4.97 out of 5 average rating, 101 reviews

Cottage w/Fire Pit Near Siesta!

Welcome to "Polka Dotted Pelican" located just a stone’s throw from world famous SIESTA KEY! This charming cottage is completely remodeled & nestled in a quiet neighborhood. Enjoy roasting s'mores around the INCREDIBLE backyard fire pit!! The living area opens to a large covered lanai for outdoor dining & relaxation. Comfortable, clean, & fully equipped! Amenities include high speed Wi-Fi, dedicated workspace, free indoor laundry, & bikes/games/beach chairs. Walk or bike to nearby Gulf Gate.

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, 108 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, 106 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 courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 126 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.96 out of 5 average rating, 149 reviews

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

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, 108 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!

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, 104 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, 102 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, 353 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.

A living area is depicted with a neutral color palette and light hardwood flooring. A blue sofa and a wooden coffee table sit in front of a television on a console. A dining area with a table and chairs is visible in the background, alongside large sliding doors leading to an outdoor space.

4.96 out of 5 average rating, 117 reviews

Siesta Beach home w/ private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.

5 out of 5 average rating, 12 reviews

Sarasota Waterfront Pool Home with Dock

Welcome to coastal elegance on Palm Island, Sarasota. - 4 bedrooms, 4 baths with modern, open layout - Gourmet kitchen with Italian Fulgor cooktop - Ground-floor master suite for privacy - Sun-filled flex room for work or relaxation - Private dock on a boating-friendly lot - Steps from Siesta Key Beach and Siesta Village - Newly renovated pool and outdoor space - Enjoy waterfront living and island tranquility

Popular amenities for house rentals near Siesta Beach

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The backyard features a newly constructed pool accompanied by a hot tub, both surrounded by vibrant greenery and tropical landscaping. A sun shelf is present in the pool, while a patio area with seating is visible in the background under the shade of trees.

4.98 out of 5 average rating, 84 reviews

Sun-filled cottage with pool, walk to beach

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, 86 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

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!

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, 92 reviews

Luxurious Private Retreat - Your Siesta Key Oasis!

A heated pool with a curved shape is surrounded by a screened patio, featuring lounge chairs positioned for relaxation. A spacious covered area showcases seating and dining options, with views of lush greenery and wooden fencing providing privacy.

4.97 out of 5 average rating, 255 reviews

Your private retreat near Siesta Key Beach.

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, 11 reviews

The Palms Away

5 out of 5 average rating, 8 reviews

Pool house with outdoor shower, 10 minutes from SK

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.

4.89 out of 5 average rating, 28 reviews

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

Weekly house rentals

5 out of 5 average rating, 9 reviews

Chic happens 3/2pool 5min from Siesta

A modern, one-story villa is showcased with a light-colored exterior. The front door is flanked by tropical palm trees and vibrant landscaping. A paved driveway leads to an attached garage, enhancing accessibility in this coastal retreat.

5 out of 5 average rating, 28 reviews

Ground floor home 2BD2BA garage Pool Private beach

An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.

4.77 out of 5 average rating, 528 reviews

Beachfront Getaway in Siesta Key

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

Superhost

New place to stay

Gulf Gate Getaway – 2BR/2BA w/ Heated Pool

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, 53 reviews

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

5 out of 5 average rating, 23 reviews

Luxe Palm Paradise • King Suite • Heated Pool/Spa

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, 39 reviews

Walk to Siesta Village, Heated Saltwater Pool

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, 75 reviews

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

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, 77 reviews

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

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

5 out of 5 average rating, 87 reviews

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

A curved swimming pool is set against a backdrop of lush tropical foliage and palm trees, with water views extending to a nearby dock. Brightly colored pots with plants are placed around the pool area, enhancing the serene outdoor setting.

4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

A bright dining area is highlighted by a wooden table surrounded by pink chairs, with a vase of tulips at the center. Large sliding doors provide views of the lush backyard, while natural light brightens the space, enhancing the inviting atmosphere.

5 out of 5 average rating, 24 reviews

Large Beach Home w/ Pool & Games on Siesta Key

Superhost

Home in Bradenton Beach

5 out of 5 average rating, 3 reviews

Walk 2 blocks to Beach + Private Pool + King Beds!

5 out of 5 average rating, 52 reviews

A serene outdoor space showcases a sparkling pool framed by lush tropical landscaping. Palms and vibrant plants surround the area, with a flamingo statue in the foreground. Soft lighting from string lights enhances the tranquil atmosphere as the sky transitions to dusk.

Home in Bradenton

Flamingo Royale — Beach Luxury Resort

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

Luxury 3BR Pool Near Beach | The Nest Siesta Key

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, 99 reviews

2 BR House 1.6 miles from Siesta Key Beach

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.

4.93 out of 5 average rating, 138 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

The modern kitchen features a large island with a marble countertop, topped with an arrangement of fresh fruits and drinks. A light fixture adds a soft glow above the island, while a cozy seating area with a dark sofa and brick wall can be seen in the background.

4.86 out of 5 average rating, 108 reviews

Sarasota Getaway “Have some fun under the sun.”

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 111 reviews

Pool house by the bay

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!

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

A private outdoor space is presented, featuring a heated saltwater pool illuminated by soft lighting. A hammock is hung nearby under a stylish frame, surrounded by lush greenery and a fenced area, enhancing the serene ambiance for relaxation.