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Vacation rentals with a pool in Sand Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sand Key

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

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Top guest favorite
The backyard features an inground pool surrounded by a smooth deck, with lounge chairs positioned beside it. Lush greenery and palm trees are seen throughout the space, enhancing the outdoor living area. A covered pergola provides shade, and a grassy area is included for relaxation.
Home in Largo
4.91 out of 5 average rating, 104 reviews

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach

Welcome to BELLEAIR BEACH OASIS! This luxuriously updated 2BR/1BA POOL HOME is minutes away from beaches and golf courses! Walking distance to Belleair grocery, coffee shops, restaurants and more. Enjoy the private and fully fenced resort-style outdoor living featuring: inground pool, modern pergola w/lounge chairs, grill, covered dining and relaxing hammock! You’ll love this quiet Belleair Bluffs neighborhood offering easy commute to St. Pete Clearwater and Tampa Airports, local hospitals, etc.

Top guest favorite
Condo in Clearwater
4.97 out of 5 average rating, 134 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Guest favorite
A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.
Guest suite in Largo
4.91 out of 5 average rating, 324 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

Guest favorite
A heated pool area features a curved blue swimming pool surrounded by a stone deck. Several lounge chairs are positioned around the pool, and umbrellas provide shade. Lush palm trees are visible in the background, contributing to the relaxed atmosphere.
Apartment in Indian Rocks Beach
4.94 out of 5 average rating, 142 reviews

Coral Reef~90° Heated Pool~Remodeled~2 min 2 beach

LOCATION! LOCATION! LOCATION! Completely renovated vacation rental located 1.5 blocks to the beautiful beach & across the street from Brown Park. This unit is located on the 2nd floor of a small two story building w/ 4 units. Out back is a large HEATED pool, lounge chairs, a dining table, grill, surfboard shower, fire pit and more. Walk two minutes down a beautiful palm tree lined path to the beach! We provide you w/ all your beach needs, towels, umbrella, beach chairs, floats and much more!

Top guest favorite
Bungalow in Indian Rocks Beach
4.96 out of 5 average rating, 198 reviews

Your private Waterfront Pool home!

See photos for City holiday event dates! Boat parade ! Street parade! Tree lighting! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

Top guest favorite
A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.
Bungalow in Indian Shores
4.96 out of 5 average rating, 174 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows + heated pool

Superhost
A peaceful heated pool area is framed by a tranquil beachfront. Loungers are arranged around the pool, with the ocean and a warm sunset visible in the background. The building's facade features balconies, offering a glimpse of the inviting coastal scenery.
Condo in Belleair Beach
4.82 out of 5 average rating, 105 reviews

Courtyard View - Steps From The Sand - Pool

We’re happy to announce that our property is open, fully operational, and in excellent condition after the recent hurricane. Book with confidence and enjoy your Florida getaway! No hidden fees or complicated check-out instructions. ☞ Free parking ☞ Pool ☞ AC ☞ Self check-in ☞ Full Kitchen Essentials (linen, towels, toiletries) are provided at the start of your stay. We recommend getting more supplies for extended stays. We are located on the beach at 3200 Gulf Blvd, Belleair Beach.

Top guest favorite
An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 167 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Top guest favorite
A heated pool is surrounded by palm trees, with two blue sunshelf loungers partially submerged in the water. Spacious chaise loungers are positioned around the pool area, featuring a light-colored stone deck and privacy provided by a wooden fence in the background.
Apartment in Indian Rocks Beach
4.97 out of 5 average rating, 151 reviews

Triplex- heated pool, bikes, walk to beach,

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared heated pool with sun shelf and chaise loungers ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior

Top guest favorite
The image captures a spacious townhouse community, featuring white architectural designs. A clear view of the intercoastal waterway is presented, with boats visible in the distance. A community pool is seen among vibrant greenery, inviting leisure and relaxation.
Townhouse in Clearwater Beach
4.99 out of 5 average rating, 117 reviews

3 Bedroom Waterfront Paradise Sleeps 8

Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

Top guest favorite
A private tiki hut features a thatched roof, ambient lighting, and a large television. Seating is provided by several lounge chairs and a unique wicker chair, arranged around a stone floor. Lush greenery surrounds the area, enhancing the outdoor experience.
Bungalow in Indian Rocks Beach
4.9 out of 5 average rating, 144 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479

Top guest favorite
Condo in Clearwater
4.99 out of 5 average rating, 115 reviews

Literally: 15 steps to the Pool, GroundFloor Condo

Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

Popular amenities for Sand Key rentals with a pool

When is the best time to visit Sand Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$47,075 GYDG$49,167 GYDG$49,167 GYDG$48,330 GYDG$46,029 GYDG$44,774 GYDG$44,564 GYDG$40,380 GYDG$41,844 GYDG$44,564 GYDG$41,008 GYDG$44,355 GYD
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Quick stats about vacation rentals with a pool in Sand Key

  • Total vacation rentals

    Explore 130 vacation rentals in Sand Key

  • Nightly prices starting at

    Sand Key vacation rentals start at G$10,461 GYD per night before taxes and fees

  • Verified guest reviews

    Over 500 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Sand Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Sand Key rentals

  • 4.8 Average rating

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

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