
Vacation rentals with a pool in Leeward
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Top-rated rentals with a pool in Leeward
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Grace Bay villa | Pool | 3min walk to Beach & Reef
A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

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!

The Sapphire Villa. Tropical Oasis. Make memories
This is where an unscripted holiday begins. At our Villa, we provide the canvas for luxury and privacy for the perfect getaway. Where dreams are fulfilled, and precious memories are made to live forever. Whatever you desire is within reach. Our Villa combines with the extraordinary tranquility of Turks and Caicos Islands for sophisticated, low-key luxury. Here is where to create your story within the privacy of your own home away from home in an exceptional place that becomes uniquely yours.

★★★★★ 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

Best deal on island! On the water w/pool!
♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders. You will need to rent a car for better convenience and freedom!

🏖🏝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 Cocuyo Micro Villa with pool
"Discover a truly unique escape at our one-of-a-kind villa in the picturesque Blue Mountain. Crafted by a local architect, this exceptional residence is nestled on a half-acre of beautifully landscaped grounds, offering an exclusive retreat in a private and secure community. Admire the lush garden in the comfort of your own oasis. The villa boasts a distinctive design that is often imitated but never duplicated, showcasing the perfect blend of style, modern layout and local charm

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!!

Villa DelEvan 4B / 1-bedrm 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.

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.

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.
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

Hopewell Villa East/Pool & walk to Gracebay Beach

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

2 Bedroom Stunning Views

Sea More Getaway

Harbour House - 2 Bed Waterfront; 7 Min to Beach
Condo rentals with a pool

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

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

**Premium Grace Bay Beach condo**

Coral Condo on Grace Bay Beach

Gated Condo in Grace Bay/ Short Walk to Everything

Amazing Grace Bay Views, Terraces Pools & Location

Cozy Studio in TCI
Other vacation rentals with a pool

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NEW Water Access! Luxe Villa, Infinity Pool& Views

Hakuna Matata Villa + Golf Cart!

Discounted Rates Luxury Private Full 1BR Suite

Darcy's place at Golf Course

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

Total vacation rentals
Explore 260 vacation rentals in Leeward

Nightly prices starting at
Leeward vacation rentals start at G$23,009 GYD per night before taxes and fees

Verified guest reviews
Over 4,930 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
260 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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