Vacation rentals with a pool in Siesta Key

Apartment in Longboat Key

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

4.96 out of 5 average rating, 114 reviews

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

Home in Indian Beach-Sapphire Shores

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

4.97 out of 5 average rating, 162 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.85 out of 5 average rating, 100 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

Aerial view showcasing a sandy beach surrounded by vibrant turquoise waters. Lush greenery is visible along the shoreline, with boats floating in the clear water. The scene captures a serene coastline, inviting guests to explore the natural beauty.

4.93 out of 5 average rating, 207 reviews

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

The Little Sandy... Your secret hideaway Incredibly located Two bedrooms, one bath Sleeps 6 easily Bring the kids...or not Walk everywhere. 3-minutes to the beach, 8 to Siesta Village Super-fast Wi-fi! Icy A/C Lovely pool Play in the water, play on the sand, play in the village Rinse and repeat Comfy beds, soft towels A great night's sleep And the best hosts on Airbnb Tradewinds included free of charge. So book now and find your Siesta-self Just like you, only funner.

A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.

4.95 out of 5 average rating, 105 reviews

Seaside on Siesta Key Beach

Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street Siesta Key Beach. NEWLY RENOVATED in 2025. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village. First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

A charming cottage is depicted with light blue wooden siding and white accents. The front yard is gravelled, surrounded by landscaping featuring mature trees and shrubs. A welcoming porch with a railing leads to the main entrance, enhancing the property's inviting look.

5 out of 5 average rating, 154 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!

4.98 out of 5 average rating, 218 reviews

Condo in Longboat Key

Oceanfront on LBK: Open Tues & Wed $199/nt + Fees!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort!

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 348 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 well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.

4.96 out of 5 average rating, 113 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 living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

4.83 out of 5 average rating, 254 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.

4.92 out of 5 average rating, 149 reviews

Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

4.92 out of 5 average rating, 116 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.

Popular amenities for Siesta Key rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

5 out of 5 average rating, 4 reviews

Luxury Waterfront Home in Sarasota w/ Pool & Dock

4.97 out of 5 average rating, 258 reviews

Your private retreat near Siesta Key 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

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

4.98 out of 5 average rating, 63 reviews

Heated pool & Infrared Sauna, 2 min to beach

4.93 out of 5 average rating, 119 reviews

A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.

Home in Saint Armands

St Armand's Mid-Century Oasis

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.

4.97 out of 5 average rating, 108 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.

4.91 out of 5 average rating, 119 reviews

Siesta Key, FL - Casa Berano

Condo rentals with a pool

A landscaped pathway is flanked by vibrant flowering plants and palm trees. Neatly trimmed grass lines the walkway, leading to a serene courtyard. Soft lighting from a garden lantern adds to the peaceful ambiance of this tropical setting.

4.93 out of 5 average rating, 159 reviews

Siesta Key Serenity At The Palm Bay Club

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 141 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.

4.95 out of 5 average rating, 137 reviews

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

4.88 out of 5 average rating, 121 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

4.89 out of 5 average rating, 196 reviews

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

An aerial view captures a landscaped area featuring a spacious pool surrounded by palm trees. The expanse of Crescent Beach is visible beyond the manicured gardens, with the ocean stretching towards the horizon under a bright blue sky.

4.88 out of 5 average rating, 102 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

4.91 out of 5 average rating, 241 reviews

A heated swimming pool is centrally located, surrounded by colorful lounge chairs in red, yellow, and green. The turquoise water is inviting under clear blue skies, with palm trees bordering the area. Nearby, several outdoor chairs are positioned for relaxation.

Condo in Sarasota

Near beach. Daily rentals. Pool. king bed

4.95 out of 5 average rating, 131 reviews

Siesta Key condo, beach access, heated pool

Other vacation rentals with a pool

A panoramic view showcases a sandy beach stretching along the coastline, framed by swaying palm trees. The tranquil azure waters of the Gulf are visible, and a few sun loungers are scattered across the beach, enhancing the serene coastal atmosphere.

4.94 out of 5 average rating, 78 reviews

Beach & Pool Open! Beachfront View All Rooms. Chai

4.81 out of 5 average rating, 21 reviews

A heated community pool is surrounded by sun loungers, offering ample space for relaxation. Palm trees dot the background, and a white fence provides privacy. Bright sky and scattered clouds create a cheerful atmosphere, enhancing the overall sunny appeal of the area.

Townhouse in Siesta Key

Villa Marina (1 Block from beach with heated pool)

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

5 out of 5 average rating, 14 reviews

Home in Holmes Beach

NEW! Coconuts 106! Beach Front! Heat Pool!

4.88 out of 5 average rating, 85 reviews

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

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.

5 out of 5 average rating, 44 reviews

Amazing beach view! Entire unit renovated!

A bright living room features a large sectional sofa adorned with various cushions. A flat-screen TV is mounted on the wall, presenting a serene beach scene. Natural light enters through sliding glass doors, which lead to a balcony, while decorative wall baskets add visual interest.

4.79 out of 5 average rating, 14 reviews

2B/2BA Penthouse End-Unit Condo

A spacious family room is presented with a large sectional couch, accented by colorful pillows. A 60-inch smart TV is mounted on a blue accent wall, showcasing a tropical scene. The dining area is visible in the background, featuring a table with light-colored chairs under modern lighting.