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Vacation rentals with a pool in Siesta Key

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Top-rated rentals with a pool in Siesta Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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An inviting pool area is surrounded by landscaped greenery and palm trees. Bright blue lounge chairs are arranged around the swimming pool on a paved deck. The building's modern architecture is visible in the background against a clear blue sky.

Condo in Siesta Key

4.95 out of 5 average rating, 130 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

Top guest favorite

A spacious kitchen showcases a large island with seating for four, surrounded by light-colored cabinetry and modern appliances. Natural light illuminates the area through large windows, providing a view of the outdoor pool. Decorative tiles and subtle backsplash add texture to the design.

Home in Siesta Key

5 out of 5 average rating, 21 reviews

Siesta Key Retreat 1mi to Beach!

Plan your SW Florida retreat to this spacious 3-bedroom, 2-bath oasis, w/ private caged pool, nestled on a quiet, peaceful street, a perfect vacation getaway for families/groups seeking relaxation and fun! Ideally located in the heart of Siesta Key a little over a mile from the #1 Beach in America! With the prime location near shops, entertainment, & 4 minutes to Siesta Beach. This charming coastal home offers smart TV in every room & a suite of variety teas/coffee pods & fully stocked kitchen!

A private pool area is framed by lush tropical landscaping, featuring palm trees and vibrant plants. Comfortable lounge chairs are positioned beside the inviting blue water. A boat dock can be seen in the background, offering scenic views of the bay.

Home in Sarasota

4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

Charming Bayfront Home in heart of Siesta Key. 3 bdrm/3.5 bath, full water views, spectacular sun rises, private, gas heated pool, boat dock/ lift, outdoor sitting area /lush tropical landscape. Open floor plan, contemporary decor, gas fireplace, hardwood floors throughout, updated kitchen, stainless steel appliances, granite counters and a full walk-in pantry. 2 Master Suites upstairs and one guest bdrm on main floor. Washer and dryer inside, 3 TV’s. Outdoor shower. Fishing. Parking for 2 cars.

A modern living space is showcased with a comfortable dark sofa and a round coffee table on a textured area rug. A dining table with four chairs is positioned nearby, while a large window offers a view of the ocean and natural light fills the room.

Condo in Siesta Key

5 out of 5 average rating, 41 reviews

Amazing beach view! Entire unit renovated!

The entire unit is completely renovated! Brand new furniture, appliances, and 2 55-inch smart TVs, etc. It comfortably sleeps 4 people. This 1 bedroom/1 bath unit include a California king bedroom set in the bedroom, queen and full sleeper sofas in the living room, and pack-n-play for infants. Big lanai area, enjoy amazing views of the ocean. This 3rd-floor unit steps away from #1 Siesta Key beach. This unit is a short distance to siesta key village for restaurants, shops, & entertainment.

A two-story blue duplex is depicted, featuring multiple windows and a welcoming porch area. The pool is surrounded by lounge chairs, while palm trees and umbrellas add a tropical touch to the outdoor space. A private patio area is visible behind the property.

Cottage in Siesta Key

4.93 out of 5 average rating, 118 reviews

The Mermaid: Heated Pool, 4 Houses to Beach

This apartment is a first-floor unit with an open floor plan that sleeps 2 with a maximum of 4 people. The bed makeup in this rental is a king bed in the master and a queen size sofa sleeper. This rental is great for longer stays or guests who like to cook since you have a full kitchen and all the items to cook any meal. There is a washer/dryer in the apartment. Beach chairs and umbrellas are supplied to you at no charge. This is a duplex and has another 1 bedroom 1 bath apartment above you.

The property features a two-story home with a light-colored exterior and a welcoming set of stairs. Tropical palm trees and green foliage frame the entrance, which is accented by vibrant blue planters. A concrete driveway leads to the house, providing ample space.

Home in Siesta Key

4.98 out of 5 average rating, 58 reviews

Quiet luxury on Siesta Key!

Enjoy a tranquil vacation at this Siesta Key paradise 3 bedroom 3.5 bath private home with an oversized heated pool. Pulling up to the lush tropical landscaped property, you will be greeted by its Key West style exterior. The outdoor section features a Grill and BBQ setup which will allow you to enjoy the view of the pristine pool area while you prepare your outdoor feast. The house is located on the north end of Siesta Key with easy access on and off the island.

Top guest favorite

Home in Siesta Key

5 out of 5 average rating, 9 reviews

Designer Home| Sleeps 10| Walk to Beach & Village|

Steps from Siesta Key Beach, this beautifully renovated 3-bedroom, 3.5-bath home offers sophisticated coastal-inspired decor. The master suite has a private screened balcony overlooking the pool with an egg chair swing. A screened patio includes bar seating, a dining area, and a cozy lounge. The first-floor mudroom has a shower for easy beach cleanup. With its classic beach cottage feel and modern amenities, this home is the perfect coastal retreat. Book now!

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 327 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

A large swimming pool is flanked by multiple lounge chairs arranged in a row. Palm trees provide shade against a clear blue sky, while tennis courts are visible in the background. The pool area is surrounded by a subtle brick patio, enhancing the outdoor setting.

Condo in Siesta Key

4.96 out of 5 average rating, 105 reviews

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

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.

Home in Sarasota

4.93 out of 5 average rating, 134 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

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 ask for!

A large heated outdoor pool is surrounded by lounge chairs, offering ample space for relaxation. The pool area is framed by palm trees, with a view of the condominium building and parked cars in the background, creating a welcoming environment.

Condo in Siesta Key

4.94 out of 5 average rating, 111 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

A freeform pool is framed by lush tropical landscaping, featuring multiple waterfalls that flow into the water. The elevated home overlooks the pool area, complemented by large windows and a wraparound balcony.

Island in Sarasota

4.97 out of 5 average rating, 330 reviews

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

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Popular amenities for Siesta Key rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

Home in Holmes Beach

4.97 out of 5 average rating, 92 reviews

Incredible BEACH HOME! Location! Heated Pool/Spa!

Top guest favorite

Home in Sarasota

5 out of 5 average rating, 66 reviews

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

Top guest favorite

A screened-in pool area features a sparkling pool surrounded by a spacious patio. Lounge chairs provide seating options, while colorful floaties rest on the water's surface. The backyard is lined with lush greenery, offering a sense of privacy and relaxation.

Home in Sarasota

4.98 out of 5 average rating, 145 reviews

Gorgeous Home / Heated Pool and Spa

Top guest favorite

A serene private pool area is framed by lush greenery and palm plants, with a view of a white fence. Two blue Adirondack chairs sit on the grass beside the pool, inviting relaxation under the sun.

Home in Siesta Key

5 out of 5 average rating, 148 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

Top guest favorite

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.

Home in Indian Beach-Sapphire Shores

4.93 out of 5 average rating, 123 reviews

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

A spacious backyard reveals a heated saltwater pool surrounded by a stone patio. Lounge chairs are positioned beside the pool, complemented by a large umbrella. An outdoor dining set is visible, along with additional seating, all nestled within a fenced environment and lush landscape.

Home in Sarasota

4.95 out of 5 average rating, 65 reviews

Stunning New 3 bed 3 bath pool home by Siesta Key!

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.

Home in Siesta Key

5 out of 5 average rating, 5 reviews

Mid-Century Modern with Pool, Canal, Mins to Beach

Top guest favorite

A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.

Home in Sarasota

4.98 out of 5 average rating, 107 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Condo rentals with a pool

A tranquil pool area is surrounded by lush greenery, with gentle palm trees swaying in the breeze. Lounge chairs are positioned alongside the clear blue water, while bright red umbrellas provide shade. Sunny skies add a bright atmosphere to the inviting scene.

Condo in Siesta Key

4.93 out of 5 average rating, 207 reviews

Steps away from beach and village! #1 in Siesta!

A spacious pool area is shown, framed with palm trees and lounge chairs under bright blue umbrellas. The inviting water reflects the sky, while a building with large windows is visible in the background, offering a comfortable area for relaxation.

Condo in Siesta Key

4.92 out of 5 average rating, 131 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

A spacious swimming pool is surrounded by palm trees and lounge chairs, reflecting clear blue skies. The pool area is well-maintained, and the building's balcony overlooks the pool, providing a serene atmosphere for relaxation.

Condo in Siesta Key

4.9 out of 5 average rating, 124 reviews

Crystal House on Siesta Key Beach

A modern living area features a comfortable sectional sofa, accented by textured cushions. A flat-screen TV is mounted on the wall above a wood panel, while large sliding doors invite natural light and provide access to the patio. Indoor plants add a touch of greenery.

Condo in Siesta Key

4.87 out of 5 average rating, 103 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

A clear heated pool is seen with shimmering blue water, accompanied by several lounge chairs positioned around the poolside. The area is landscaped with greenery, and a shaded pavilion is observable in the background.

Condo in Longboat Key

4.87 out of 5 average rating, 107 reviews

Sunset and beach view from your balcony Unit 403

A clear view of one of the community heated pools is presented, featuring a spacious area surrounded by palm trees. The pool's depth is marked as 3 feet 7 inches, with lounge chairs placed around its perimeter for relaxation.

Condo in Siesta Key

4.81 out of 5 average rating, 323 reviews

[Beach Elements] pool view + private beach & bikes

Condo in Longboat Key

4.92 out of 5 average rating, 179 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Top guest favorite

An oceanfront view is captured from the private lanai, showcasing the serene blue waters of the Gulf of Mexico and a heated pool below. Palm trees frame the scene, and beachgoers can be seen in the distance enjoying the sandy shore.

Condo in Longboat Key

4.98 out of 5 average rating, 194 reviews

Condo with a View 1: Oceanfront!

Other vacation rentals with a pool

The open-concept kitchen and dining area feature modern furnishings, with a spacious table for six and bar seating along the kitchen island. Floor-to-ceiling windows provide unobstructed views of the beach, allowing natural light to brighten the room.

Condo in Sarasota

5 out of 5 average rating, 8 reviews

Stunning Siesta Vistas Direct Beach Access & Pool

Condo in Siesta Key

4.98 out of 5 average rating, 58 reviews

Amazing SK beach views... Newly renovated condo!!!

A bright living area features large floor-to-ceiling windows that allow natural light to fill the space. A light-colored sectional sofa and a modern coffee table are present, along with a floor lamp. A balcony is visible in the background, showcasing views of greenery.

Condo in Siesta Key

4.9 out of 5 average rating, 48 reviews

Beach Haven on Siesta Key Beach

Top guest favorite

A sheltered dining area is seen under a striped umbrella, featuring a large table surrounded by white chairs. A small heated pool is located nearby, complemented by lush greenery and colorful tropical plants lining the perimeter.

Townhouse in Siesta Key

4.98 out of 5 average rating, 50 reviews

Siesta Sunrise-Just steps to the beach and village

A central pool area is surrounded by lush palm trees and greenery, offering a spacious swimming pool with sun loungers arranged around its edge. The buildings on either side provide shaded balconies, contributing to a relaxed atmosphere within the community.

Condo in Siesta Key

4.88 out of 5 average rating, 59 reviews

Cozy Top-Floor Stay on Siesta Key

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.

Home in Sarasota

5 out of 5 average rating, 34 reviews

Stunning Home, Heated Pool and Boat Dock

A clear blue swimming pool is surrounded by palm trees, with lounge chairs and shaded areas positioned nearby. A low fence borders the pool, and the backdrop features a single-story building set among well-maintained greenery under a bright blue sky.

Condo in Siesta Key

4.95 out of 5 average rating, 81 reviews

Casa Mar Steps 2 Siesta Key, Pool, Tennis, & More!

An aerial view of the Gulf and Bay Club Bayside community showcases a cluster of two-story buildings surrounded by lush greenery. A central pool area is visible, along with scenic waterways and palm trees, emphasizing the tranquil atmosphere of the neighborhood.

Condo in Siesta Key

5 out of 5 average rating, 7 reviews

Spacious 2BR 2nd floor Siesta Key condo - GBB 1274

Quick stats about vacation rentals with a pool in Siesta Key

Total rentals
1.6K properties
Nightly prices starting at
G$12,555 GYD before taxes and fees
Total number of reviews
25K reviews
Family-friendly rentals
1.3K properties are a good fit for families
Pet-friendly rentals
240 properties allow pets
Rentals with dedicated workspaces
800 properties have a dedicated workspace

Destinations to explore