
Vacation 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.

Flame Tree Cottage|Ocean view&pool.Walk to beach
Built in 2013. 1 bedroom 2 bathroom cottage with PRIVATE POOL. Sunrise & ocean view from the front deck and only 1/4 mile to the beach. Perfect for 2, but can sleep up to 6. Full kitchen, 2 bathrooms + outdoor shower. No bathtub. Propane Grill. AC in master bedroom. WIFI throughout & local cell provided. This quaint clutter-free 1200 square foot home is surrounded by indigenous foliage, cactus', succulents and native stonework. A rental car is recommended to explore all the island has to offer!

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.

Luxury Spacious 1 Bed Condo close to the Beach
Just renovated: The perfect condo, and only 3 minutes from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. This 925 sqft luxury 1 bedroom, freshly renovated (Jan 2023), provides all necessary amenities for your home away from home.

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.

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.

Tropical Guest House
This stylish studio sits within a lush tropical garden behind a semi-detached villa. Enjoy cold AC, a well-equipped space, and your own private grill. Grace Bay Beach is just a 15-minute walk—or less than a minute by car—making it easy to enjoy one of the world’s most beautiful shorelines. Coco Bistro, a renowned island restaurant, and Coco Van are close by, with shops and a grocery store also within easy reach. A fantastic location, great value, and close to everything! 🏠🌴

*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.

Villa DelEvan 4D / 1-bedroom 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.

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

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.

Island Vibes Condo at The Plaza
This unit is a two Bedroom 2.5 Bathroom condo centrally located in the Ocean Club Plaza on Grace Bay Road... This impeccably maintained condo sits in the right location for you to enjoy the best of what the island has to offer, with a short strut to the world famous Grace Bay Beach through the lush pathways within the Ocean Club West Resort. This unit is perfect for a couple’s getaway or a family of 4.

Charming Gecko House with porch & pool - Grace Bay
Affordable and charming house situated in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the world famous Grace Bay Beach. Very popular with solo travelers and couples. Close to the beach and steps away from the very popular Coco Bistro Restaurant and Coco Van.
Popular amenities for Leeward rentals with a pool
House rentals with a pool

Calme at Oceanside PrivatePool OceanView SunSet

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

Hopewell Villa East/Pool & walk to Gracebay Beach

2 Bedroom Spectacular Views

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

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

The Sapphire Villa. Tropical Oasis. Make memories

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views
Condo rentals with a pool

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

Grace Bay Luxury Gated 1400 sq ft 2 Bedroom Condo

Stylish Grace Bay Condo | Top Floor w/ Den + Pool

Crystal Vista Suite

**Premium Grace Bay Beach condo**

Amazing GraceBay Views, Pools,Location PH Studio

★★★★★ Modern Condo | Amazing Pool | On Site Spa

NEW! Romantic Getaway, 3 Mins to the Beach !
Other vacation rentals with a pool

Perfect for 1 Couple - Pool & Beach access

TC Villas | Nutmeg | Cozy Retreat & Poolside Bliss

SunSeaSand Seaside Studio Unit A - Long Bay Hills

Unwind, Swim & Dine Nearby

Pristine beach 5 min away | Pools | Jacuzzi | Gym

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

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

Discounted Rates Luxury Private Full 1BR Suite 2
Quick stats about vacation rentals with a pool in Leeward

Total vacation rentals
Explore 270 vacation rentals in Leeward

Nightly prices starting at
Leeward vacation rentals start at G$29,291 GYD per night before taxes and fees

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

Family-friendly vacation rentals
210 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
270 of Leeward vacation rentals include wi-fi 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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