Holiday rentals with a pool in Sarasota Beach

4.94 out of 5 average rating, 101 reviews

A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.

Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

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, 126 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 from Siesta Key Beach. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village, Stickney Point, or Turtle Beach 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.

4.79 out of 5 average rating, 110 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

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, 110 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.

4.96 out of 5 average rating, 153 reviews

A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.

Home in Sarasota

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

Welcome to your home away from home! This renovated, spacious, and bright pool home will immerse you in a luxurious experience the minute you arrive. Located on a lush, quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in the USA), 10 minutes to downtown (with fantastic restaurants and shopping), and within walking distance of the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake Park, and the new UTC mall!

Superhost

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

Home in Sarasota

4.8 out of 5 average rating, 188 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

4.94 out of 5 average rating, 142 reviews

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

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!

4.92 out of 5 average rating, 171 reviews

Apartment 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 modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.

4.88 out of 5 average rating, 177 reviews

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

A spacious and quiet 2-floor, 2 bedroom, 2.5 bathroom condo that lives like home and is close to everything Siesta Key offers. Spread out and enjoy YOUR vacation! Your condo features large rooms, comfy and modern surroundings, (2) Master Bedrooms upstairs, and you are steps away from a gorgeous heated pool that you can view from your lanai. This is the perfect condo for you and your family to relax in and simply enjoy your time in Siesta Key!

Home in Gulf Gate Estates

A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.

4.8 out of 5 average rating, 137 reviews

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

4.86 out of 5 average rating, 173 reviews

Townhouse in Siesta Key

Luxury Siesta Key Compound | Pool | Walk to Beach

Luxury Beachside Retreat ✨🌊 Just steps from Siesta Key’s Public Beach, this 1,850 sqft 3BR/2.5BA townhouse offers 2 king bedrooms and a romantic loft with queen bed, private balcony + stunning Gulf views. Max. 6 guests. All 3 balconies overlook the beach. Enjoy a heated lagoon pool (shared by only 2 duplexes), free Wi-Fi, beach chairs, umbrellas & parking for 2–3 cars. The best location for your Siesta Key escape!

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.