
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 Condo | Amazing Pool | On Site Spa
• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub (under consrtuction until mid-Nov) • Highest Rated Spa on Island • 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 • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

🏖🏝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 🏝

Romantic Apartment few steps from beach
Wake up to the soothing melody of a mockingbird in the garden, as gentle sunlight filters through the lush greenery. Sip your morning coffee on the balcony, overlooking the tropical garden and sparkling crystal-clear pool, where the peaceful ambiance sets the tone for a romantic escape. Afterward, take a leisurely stroll through the vibrant garden or wander just a few minutes to the nearest beach with turquoise waters and soft white sands, perfect for a tranquil start to your day.

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.

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

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.

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.

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.

Modern Micro Villa / Pool 5 Minutes to Beach
Villa Cocuyo offers complete privacy, comfort, and consistent 5-star 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.

Villa Jayla
Villa Jayla is located on the south side of Providenciales approximately 1 mile from the famous sapadilla and Taylor bay beaches. the Beautiful Villa sits on the south side of the Island over looking the sound where you can go kayaking or chill and look at the beautiful sunset. We now have a paddle board!

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞
Welcome to this immaculate 'piece of paradise' at the exclusive 'Yacht Club' Turks and Caicos..Enjoy the beautiful Caribbean sun setting over Turtle cove marina any day of the year from the comfort of your own terrace. Please note this is a strictly - NO SMOKING apartment even on the terrace . Thank you
Popular amenities for Leeward rentals with a pool
House rentals with a pool

Leeward Landing Villa

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

Gated Villa + Private Pool• Walk to GraceBay Beach

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

The Sapphire Villa. Tropical Oasis. Make memories

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views

2 Bedroom Stunning Views

Sea More Getaway
Apartment rentals with a pool

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

*Balcony View* Modern Studio C202

Couple’s Retreat - ocean view, pool and hot tub!

**Premium Grace Bay Beach condo**

NEW! Romantic Getaway, 3 Mins to the Beach !

Shore to Please - Large Studio Condo with Patio

Gated Condo in Grace Bay/ Short Walk to Everything

Darcy's place at Golf Course
Other holiday rentals with a pool

SunSeaSand 1Bdrm Seaside Unit B- Long Bay Hills

Grace Bay modern 2 bedroom poolside condo

1 BR Villa | Island Escape | December DEAL!

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

NEW *2 BR Villa Kiwi- BBQ- Pool in Grace Bay Beach

Davijon Villa

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 260 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at $143 SGD per night before taxes and fees

Verified guest reviews
Over 4,930 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
260 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!
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