
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 Honeymoon Villa
Luxurious Gated Villa near Grace Bay Beach– Private Pool & Jacuzzi♨️ Escape to this luxury villa, just 2 minutes by car or a 10-min walk from Grace Bay Beach. Relax in your private infinity pool or rooftop jacuzzi with ocean view. The villa features 2 outdoor balconies, a modern kitchen with new appliances, and fast fiber internet. Perfect for 2 guests, this private retreat offers comfort, style, and Super host service. Close to dining, shopping, and activities. Book your dream vacation today🌴

OCEAN ORCHID
This fabulous penthouse apartment is located within the exclusive Turtle Tail Marina and next to the late singer Prince's house. This newly built 3 large en suite bedroom apartment offers beautiful ocean and marina views from every room and balconies. The outdoor BBQ area has views of the ocean and Flamingo Lake where you can socialize, chill and spot the odd pink flamingo. There is a large pool with loungers and a hammock for relaxing, kayaks are available to explore the small cays and beach.

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.

Cozy Studio in TCI
My cozy studio is located in La Vista Azul Resort in Turtle Cove, Providenciales. It is perfect for a solo traveler and a tight squeeze for a couple. This is my home away from home, so please take good care of it :) Living in the Caribbean is great, but it does come with some downsides i.e. bugs/insects and expensive utilities. PLEASE keep the DOOR CLOSED at all times to keep the bugs and insects out of the unit, and PLEASE turn off the lights, TV, and AC when leaving the unit. Enjoy!

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.

Modern 4BR oasis on 1 acre, 1 min from the Beach
Legacy Palms Villa is an ideal oasis for visitors to Providenciales. Set on an acre of private land, this secluded location provides privacy and tranquility. Kick back and relax by the pool with tons of natural shade from the beautiful palm trees and natural island vegetation or take a 10 minute walk to the beach. The villa is also a short 5 minute drive to the popular Grace Bay strip where you can find many different restaurants, tourist attractions, shopping, and grocery stores.

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! 🏠🌴

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!!

Leeward Landing Villa
Escape to paradise at Beach Landing Villa nestled in the heart of Leeward TCI. This luxurious villa is just minutes away from the pristine award-winning Grace Bay Beach offering a perfect blend of relaxation and adventure. Conveniently cruise your community in your 6-seater Golf Cart or pedal along with the (2) provided pedal bikes. Or relax out by the pool in your private back yard! Book your villa now for an unforgettable experience in paradise!
Popular amenities for Leeward rentals with a pool
House rentals with a pool

Waterfront Turtle Tail Villa | Pool & Kayaks

Hopewell Villa East/Pool & walk to Gracebay Beach

Perroquet | Family Villa Leeward

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

NEW Water Access! Luxe Villa, Infinity Pool& Views

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

Sea More Getaway

Modern Caribbean - Amazing views & Private Pool
Apartment rentals with a pool

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

Amazing Ocean views -Modern Condo -Balcony - Pool

*Balcony View* Modern Studio C202

Grace Bay Luxury Gated 1400 sq ft 2 Bedroom Condo

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

Shore to Please - Large Studio Condo with Patio

La Vista Azul Condo steps from Grace Bay Beach
Other holiday rentals with a pool

Apt with private pool and direct beach access

Cocotini

Sea Villa - Cozy Family Villa Steps From the Beach

Hakuna Matata Villa + Golf Cart!

Lovely studio apartment, with pool

Luxury 4Bed/4.5Bath/Pool Townhome

Pristine Oceanfront 2-Bed Condo

Harmony Palm 3BDR Villa | Grace Bay Beach Chairs
Quick stats about holiday rentals with a pool in Leeward

Total holiday rentals
Explore 280 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at £81 per night before taxes and fees

Verified guest reviews
Over 5,920 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wifi availability
280 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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