
Holiday rentals with a pool in Leeward
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Leeward
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Ideal private getaway villa | 250 yds to the beach
The perfect getaway villa, just 250 yards from Grace Bay beach, Gracehaven Getaway is tucked away from passing traffic in a little garden oasis of its own. It is an ideal venue to celebrate anniversaries, birthdays, or honeymoons, or just for a couple seeking a romantic, private setting. Enjoy your own private pool hidden away from main roads and just a 2-minute walk to the Grace Bay beach and Coral Gardens Reef. Easily walk to local restaurants or visit the nearby supermarket for groceries.

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝
🏖 NEWLY RENOVATED, SPACIOUS one bedroom condo with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the unit is close to several excellent restaurants, cafes, bars, a casino, and a marina. Most notably, the studio is a 10 minute walks to Smith's Reef in the Princess Alexandra Park National beach. Smith’s Reef is located near Turtle Cove on the north coast of Providenciales, and about 3.5 miles (5.6 km) from Grace Bay 🏝

Gated Condo in Grace Bay/ Short Walk to Everything
This studio in Grace Bay offers comfort and convenience. It's a few minutes walk to the beach, grocery stores, restaurants, activities, and a medical center. The Caicos Key condo is new and includes a 55-inch smart TV with Fire Stick, fast Wi-Fi, a dishwasher, and a washer/dryer combo. For your security, the property has a smart lock and is gated. Guests can also use the swimming pool and BBQ area. We aim to make your stay comfortable and can provide anything you need on demand.

Villa DelEvan 4A / 1-bedrm Beach front villa
Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

*Balcony View* Modern Studio C202
Welcome to our little piece of paradise in Providenciales, Turks and Caicos. We hope that you will enjoy our modern style condo as much as we do. Our condominium is situated at Queen Angel Resort, walking distance to the #1 beach in the world, Turtle Cove Marina, and Smith’s Reef the best snorkelling spot on the island. Turtle Cove is a tourist hot spot with many restaurants, excursions and attractions available. The condo has recently been fully renovated and remodelled.

Juba Sunset
Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Modern Villa with Private Pool Near Long Bay Beach
- Immerse yourself in tranquil luxury at a gated two-story villa just minutes from Long Bay Beach. - Enjoy bright, spacious interiors, a modern kitchen, and a private, secure setting throughout. - Relax by the private pool, fire up the BBQ, and unwind in peaceful outdoor lounge areas. - Stay connected with fast WiFi and explore Grace Bay’s beaches, shops, and dining nearby. - Reserve your stay for a refined tropical retreat designed for comfort and relaxation.

1 Bedroom Luxury Grace Bay Condo in Best Location
The perfect location, and only a 5 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 5 minute walk to the beach. 2 minute walk to the best grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.

Modern Villa with Pool Minutes to Grace Bay Beach
Villa Cocuyo offers complete privacy, comfort, and consistent 5⭐️ hospitality. Couples love the safe and secure , peaceful setting, private solar heated pool, modern interior, and garden oasis. Enjoy fast WIFI, premium amenities, and a spotless space designed for true relaxation. Our 5-star reviews reflect our dedication to exceptional hosting, attention to detail, and a worry-free, private island getaway close to everything including beach

★★★★★ Modern Condo | Amazing Pool | On Site Spa
• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island onsite • Fully equipped kitchen • Private front patio • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Cheers 🥂 Villa 🌴
Beautiful private Villa in a superb location. Just 2 minutes by car, or 10 minute walk to Grace Bay Beach & Shopping! Cheers Villa is filled with love ❤️ where you can relax in peace during your holiday. We have all the essentials to enjoy the climate of Turks & Caicos. You can relax by the private pool after a day at the beach! 2 bedrooms (King & Queen) 2.5 bathroom. Each room has its own AC as well as the downstairs living space.

Leisure in Paradise - steps from Beach, with pool
Wake up on a Mocking bird singing in the garden, sun rays sparkling through the lush green while you drink your cup of tea or coffee on your private screened patio. Take a walk in the topical garden and have a refreshing swim in crystal clear pool or take a short walk (3 minute) to the turquoise ocean and white sandy beach.
Popular amenities for Leeward rentals with a pool
House rentals with a pool

Leeward Landing Villa

Tropical Carabas Villa!

Calme at Oceanside PrivatePool OceanView SunSet

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

Hopewell Villa East/Pool & walk to Gracebay Beach

“The Lighthouse”, Private Pool, Ocean Views, Beach

1 BR Apt w/pool - Long Bay Hills #2

The Sapphire Villa. Tropical Oasis. Make memories
Apartment rentals with a pool

🌴 YOUR STUNNING BEACH HOME IN PARADISE 🌞

Grace Bay Hideaway. 1 bedroom, central Grace Bay.

Crystal Vista Suite

1BR Sand Dollar Stay in Grace Bay, Turks & Caicos

NEW! Romantic Getaway, 3 Mins to the Beach !

Shore to Please - Large Studio Condo with Patio

The Queen Conch of Queen Angel

Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!
Other holiday rentals with a pool

Perfect for 1 Couple - Villa w/Pool & Beach access

SunSeaSand Seaside Studio Unit A - Long Bay Hills

Oceanview Studio: Steps away to Grace Bay Beach

NEW *2 BR Villa Maya- BBQ- Golf- Pool in Grace Bay

Grace Bay Studio

OCEAN PEARL-getaway retreat nearby sunset beach

Discounted Rates Luxury Private Full 1BR Suite 2

Caicos Retreat Apt#3
Quick stats about holiday rentals with a pool in Leeward

Total holiday rentals
Explore 270 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at $178 SGD per night before taxes and fees

Verified guest reviews
Over 5,420 verified reviews to help you choose

Family-friendly holiday rentals
210 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
270 of Leeward holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Leeward rentals

4.8 Average rating
Leeward stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Santiago De Los Caballeros Holiday rentals
- Santo Domingo Este Holiday rentals
- Puerto Plata Holiday rentals
- Sosúa Holiday rentals
- Cabarete Holiday rentals
- Juan Dolio Holiday rentals
- Jarabacoa Holiday rentals
- Boca Chica Holiday rentals
- Bonao Holiday rentals
- Río San Juan Holiday rentals
- Villa rentals Leeward
- Rentals with a patio Leeward
- Fitness-friendly rentals Leeward
- Waterfront rentals Leeward
- Rentals with a hot tub Leeward
- Family-friendly rentals Leeward
- Pet-friendly rentals Leeward
- Rentals with a kayak Leeward
- Rentals with a washing machine and dryer Leeward
- Beachfront rentals Leeward
- Luxury rentals Leeward
- Flat rentals Leeward
- Rentals with beach access Leeward
- House rentals Leeward
- Rentals with a firepit Leeward
- Rentals with outdoor seating Leeward
- Rentals with pools Providenciales
- Rentals with pools Caicos Islands
- Rentals with pools Turks and Caicos Islands




