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Vacation rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

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, 131 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

An expansive backyard features a private heated pool, surrounded by lounge seating and a well-maintained putting green. Softly glowing twilight casts a warm hue over the space, framed by lush greenery and a serene atmosphere.

Home in Sarasota

5 out of 5 average rating, 108 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from BOTH Lido Key and Siesta Key Beach, this incredible stay includes: ✔ Backyard Putt-Putt Course ✔ Private Heated Saltwater Pool w/ Lounge Chairs ✔ Covered Patio w/ String Lights ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included!

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, 109 reviews

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

Your "Beach Home" w/ heated pool is a private home 1 and 1/4 mile drive to Beach Access 12 on Siesta Key. 3bedroom/2bathroom. It's ideal for families/couples. Everything you need for a great vacation!Fully equip kitchen,towels/linen, laundry room . Large pool w/ gas bbq & patio area. Use our chairs, cooler,umbrella,beach cart.STRICT OCCUPANCY OF MAX 6 PEOPLE INCLUDING INFANTS/KIDS AT HOUSE. NO OUTSIDE GUESTS DAY/NIGHT. DO NOT BOOK IF YOUR GROUP IS LARGER. No Pets. Min Age 26 to book

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.

Condo in Longboat Key

4.91 out of 5 average rating, 181 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

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

4.94 out of 5 average rating, 125 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.

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, 150 reviews

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

FULLY RESTORED POST HURRICANE! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time and post hurricane updates! If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 331 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!

The image features a sparkling blue pool surrounded by a spacious patio area. Palm trees and lush greenery enhance the scenery, while the nearby Tiki Hut provides shaded seating. The backdrop includes a serene view of the water, with boats visible in the distance under a partly cloudy sky.

Condo in Siesta Key

4.84 out of 5 average rating, 244 reviews

Cozy 1BR Beach Condo on Siesta Key!

Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

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, 113 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, 333 reviews

NEW 4/NTS AUG 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!

Top guest favorite

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Sarasota

5 out of 5 average rating, 110 reviews

Tropical Luxury: Pool, Game Room, Near Beaches

Welcome to your luxury, pet-friendly retreat! Just 15 min to Siesta & Lido beaches and the airport, this 4-bed oasis packs resort vibes into one easy stay. Heated pool & covered game room Sun-filled lounge, fire-pit & fenced yard Plush luxury beds for dreamy sleep Chef-ready kitchen, washer & dryer Unwind, explore, repeat—your tropical getaway starts here.

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

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 Sarasota

5 out of 5 average rating, 66 reviews

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

Top guest favorite

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.

Home in Sarasota

4.97 out of 5 average rating, 248 reviews

Your private retreat near Siesta Key Beach.

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.

Home in Sarasota

4.93 out of 5 average rating, 101 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

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, 23 reviews

Siesta Key Retreat 1mi to Beach!

A private heated pool is featured in a landscaped outdoor area, surrounded by smooth stone tiles. Colorful plants add vibrancy to the space, while a flowing water feature enhances the serene atmosphere.

Home in Holmes Beach

4.94 out of 5 average rating, 113 reviews

The Peachy Beach House, steps to the gulf

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, Pool, Mins to Siesta Key Beach

Top guest favorite

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Sarasota

5 out of 5 average rating, 27 reviews

Sarasota Escape | Minutes to Beaches + Downtown

A private heated saltwater pool is framed by a spacious patio area, featuring lounge chairs and a shaded outdoor dining space. An outdoor kitchen is equipped with a grill, while the multi-level home above is illuminated, showcasing balconies with seating. Lush palm trees add a tropical touch.

Home in Siesta Key

5 out of 5 average rating, 8 reviews

Escape | Walking Distance to SK Beach!

Condo rentals with a pool

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

Condo in Siesta Key

4.85 out of 5 average rating, 181 reviews

Best Siesta Key Condo

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 tranquil pool area is surrounded by palm trees, with the beach visible in the background. Loungers with umbrellas are set up along the pool's edge, inviting relaxation. The American flag gently waves above, complementing the serene coastal atmosphere.

Condo in Siesta Key

4.83 out of 5 average rating, 115 reviews

Beach Retreat - Jamaica Royale Unit #52

A large heated pool is visible, surrounded by lounge chairs for relaxation. Tall palm trees frame the area, and the building's exterior provides a backdrop. The clear blue water reflects the sunny sky, inviting guests to enjoy a refreshing swim.

Condo in Sarasota

4.86 out of 5 average rating, 152 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

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, 324 reviews

[Beach Elements] pool view + private beach & bikes

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, 110 reviews

Sunset and beach view from your balcony Unit 403

The pool area features a heated pool surrounded by paved stone flooring. Several outdoor tables and chairs are positioned nearby, with shade provided by a thatched-roof gazebo. Palm trees and tropical plants create a relaxing atmosphere, while a view of the Intracoastal waterway is visible in the background.

Condo in Siesta Key

4.94 out of 5 average rating, 170 reviews

Sea Club 2 - Relaxing Siesta Beach Key Condo Renta

Condo in Siesta Key

4.94 out of 5 average rating, 127 reviews

2/1 bayside, deeded beach access, heated pool

Other vacation rentals with a pool

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, 51 reviews

Beach Haven on Siesta Key Beach

A spacious two-level retreat is viewed from above, showcasing a modern exterior with multiple balconies. Lush greenery surrounds the property, complementing the contemporary architectural lines. The pool area is nestled amidst palm trees, creating a serene atmosphere near the waterfront.

Home in Siesta Key

4.96 out of 5 average rating, 46 reviews

Private Pool & beach access, Garage, beach toys

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

4.89 out of 5 average rating, 62 reviews

Cozy Top-Floor Stay on Siesta Key

A crystal-clear swimming pool is framed by a brick patio, surrounded by lounge chairs. The pool area is bordered by a white fence, with palm trees and landscaping adding a tropical feel. The scene is set in a communal outdoor space, inviting relaxation.

Condo in Siesta Key

5 out of 5 average rating, 5 reviews

A New Listing - Siesta Key Beach Front!

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, 42 reviews

Amazing beach view! Entire unit renovated!

Top guest favorite

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

Home in Sarasota

4.98 out of 5 average rating, 93 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

A clear, inviting heated pool is surrounded by lounge chairs, offering a relaxing atmosphere. Lush palm trees and other greenery enhance the pool area, while a covered pavilion with a grilling area is visible in the background.

Condo in Sarasota

4.94 out of 5 average rating, 53 reviews

Top Floor Beautiful View Condo-Shore To Please

An aerial view captures the expansive property layout, featuring well-maintained grounds, a central pool area, and two tennis courts. Lush palm trees surround the space, framing concrete pathways and parking areas, with the Gulf of Mexico visible beyond the buildings.

Condo in Sarasota

5 out of 5 average rating, 29 reviews

Beachfront - 2BR - Spectacular Beach Setting

Quick stats about vacation rentals with a pool in Siesta Key

Total rentals
1.6K properties
Nightly prices starting at
R1,062 ZAR 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