
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.

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.

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.

"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.

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!

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

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

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.

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!

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

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.

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

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
House rentals with a pool

Cozy Stylish Home w/ Heated Pool & Big Parking

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront Townhome w/Game Room & Boat Slip! Walk

Piece of paradise in Indian Rocks Beach.

Stunning views! Spot dolphins from the pool!

Palm Paradise - Family Amenities+Central Location

Dolphin Dreamer-6-Seat Golf Cart!

Clearwater Gameroom- Pool/Mini golf/Home Theatre
Condo rentals with a pool

Blue Sea Renity -Steps to Beach| Heated Pool

Seaside Paradise at Clearwater - Resort Style

Modern and Cozy Condo 6 Minutes from the Beach !

Condo Conveniently located to Clearwater Beach

2 King Suites • Waterfront • Walk to Beach

Beach Days & Family Fun - Last Minute Openings

Royal Orleans and Redington Beach ( Studio 203 )

Five Star Beachfront Condo Newly Renovated
Other vacation rentals with a pool

Hgtv Style Pool Home, Across the Street from Beach

IRB Harbor House Semiprivate Waterfront Pool Villa

Modern 1 bedroom condo at Avalon

Pool | Patio | Kitchen | Gym | Self Checkin | WiFi

Awesome Condo in Clearwater, FL

Sonrisa 1 - | Beachfront Condo in Belleair Beach

Largo Paradise w/ King Bed - Pool - 3.9mi to Beach

Private Backyard Oasis* Heated Salt Pool - Hot Tub
When is the best time to visit Sand Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$47,075 GYD | G$49,167 GYD | G$49,167 GYD | G$48,330 GYD | G$46,029 GYD | G$44,774 GYD | G$44,564 GYD | G$40,380 GYD | G$41,844 GYD | G$44,564 GYD | G$41,008 GYD | G$44,355 GYD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
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!
Destinations to explore
- Condo rentals Sand Key
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- Rentals with a washer and dryer Sand Key
- Rentals with beach access Sand Key
- Rentals with a sauna Sand Key
- Family-friendly rentals Sand Key
- Beachfront rentals Sand Key
- Rentals with a hot tub Sand Key
- Waterfront rentals Sand Key
- Apartment rentals Sand Key
- Rentals with a patio Sand Key
- Beach condo rentals Sand Key
- Fitness-friendly rentals Sand Key
- Rentals with pools Clearwater
- Rentals with pools Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Busch Gardens Tampa Bay
- John's Pass
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park
- Busch Gardens
- North Beach At Fort DeSoto Park




