Holiday rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Siesta Key

  • Total holiday rentals

    Explore 1,820 holiday rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key holiday rentals start at $86 AUD per night before taxes and fees

  • Verified guest reviews

    Over 29,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,530 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 310 rentals that welcome pets

  • Rentals with dedicated workspaces

    890 properties have a dedicated workspace

  • Wi-Fi availability

    1,790 of Siesta Key holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Siesta Key rentals

  • 4.8 Average rating

    Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!

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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Guest favourite
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.
Condo in Siesta Key
4.86 out of 5 average rating, 106 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.

LocationFamilyAccess

Top Guest favourite
Condo in Longboat Key
4.98 out of 5 average rating, 241 reviews

Island Time: Open July 7 - 10!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! 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 secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

ValueLocationAccuracy

Guest favourite
Home in Sarasota
4.93 out of 5 average rating, 397 reviews

Heated&Renovated Pool•Beach Retreat•15m to Siesta

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

LocationFamilyKitchen

Top Guest favourite
A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.
Home in Sarasota
4.95 out of 5 average rating, 242 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

LocationFamilyQuiet

Guest favourite
A mid-century modern home is framed by a large tree, with white walls reflecting the surrounding greenery. Potted plants add color to the entrance, while two decorative faces are positioned on a stone ledge. The area is bordered by white gravel, enhancing the peaceful ambiance.
Home in Siesta Key
5 out of 5 average rating, 13 reviews

Siesta Key | Heated Pool | Sauna | Family & Pets

☞ Sauna, Fire-pit, BBQ (gas) ☞ Giant Outdoor Chess♟️ ☞ King & 2 Queen Beds ☞ Ample Parking (RV, Boat, etc) ☞ Fast WiFi 🛜 ☞ 4 Smart TVs (largest 85 inches) ☞ Gourmet Kitchen Main side ☞ Kitchenette on Guest side ☞ 2 Onsite washer + dryers ☞ 2 Outdoor Showers 》30 mins to airport 》2 mins to Siesta Key Beach Bike to America’s #1 beach, morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.

LocationFamilyHospitality

Top Guest favourite
Home in Siesta Key
4.97 out of 5 average rating, 33 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.

FamilyLocationBeach

Guest favourite
A spacious bedroom features a large king-size bed dressed in neutral linens. A flat-screen television is mounted on the wall, while natural light enters through sliding glass doors. A small table and a decorative plant add a touch of elegance to the minimalist decor.
Condo in Siesta Key
4.83 out of 5 average rating, 343 reviews

[Beach Elements] pool view + private beach & bikes

Relax & Recharge at Siesta Beach in a poolside one-story villa. +2 beach cruiser bikes ( $40 each per stay) NEWLY REMODELED!! King size bed + queen sofa bed This modern studio is fully equipped with a kitchen, granite countertops & stainless steel appliances.  King size bed and full-size sleeper sofa. Recently updated kitchen, bathroom, and a complete living area. It overlooks 1 of 3 pools Enjoy the morning sun, with your coffee on the patio.

ValueFamilyAir conditioning

Guest favourite
Home in Siesta Key
4.85 out of 5 average rating, 117 reviews

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

Escape to this colorful 2BR beachfront duplex in the heart of Siesta Key, just steps from the beach, restaurants, and local attractions. Enjoy modern comforts, a private cabana with a hot tub, and access to a shared pool—perfect for couples, families, and beach lovers. ☀ Shared pool ☀ Steps to the beach ☀ Pet-friendly ☀ BBQ area ☀ Private hot tub ☀ Pets allowed ☀ Wifi & Free parking Your perfect seaside escape awaits!

FamilyValueAmenities

Superhost
Home in Siesta Key
5 out of 5 average rating, 3 reviews

Bahama Mama | Tropical Retreat on Siesta Key

Bahama Mama is a five-bedroom, five-bath island retreat just a five-minute walk to Siesta Key Beach 🌊. Enjoy a private tropical backyard with a pool, spa, covered patio, BBQ, and outdoor dining. Inside features coastal décor, a fully equipped kitchen, and ensuite baths for every bedroom. Steps from Siesta Key Village shops and restaurants, this home is perfect for families or groups seeking the ultimate beach getaway! 🏖️✨

LocationBeachHot tub

Top Guest favourite
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.
Condo in Siesta Key
4.97 out of 5 average rating, 382 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.

FamilyLocationCleanliness

Top Guest favourite
Home in Arlington Park
4.97 out of 5 average rating, 33 reviews

Modern Home Heated Pool near Siesta & Downtown

Escape to our brand-new, modern Sarasota home, perfect for families! Enjoy a private heated saltwater pool just steps from the master suite. Located minutes from the world-famous Siesta Key Beach and vibrant downtown Sarasota. This stylish oasis comfortably accommodates up to 10 guests, offering the ultimate Florida retreat with all-new furnishings and a fully equipped kitchen. Your private getaway awaits!

FamilyLocationIndoor spaces

Top Guest favourite
Home in Sarasota
4.98 out of 5 average rating, 116 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

LocationValueSleep quality

Popular amenities for Siesta Key rentals with a pool

When is the best time to visit Siesta Key?

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Avg. price$402 AUD$526 AUD$586 AUD$447 AUD$350 AUD$352 AUD$352 AUD$321 AUD$288 AUD$297 AUD$331 AUD$389 AUD
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