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Waterfront holiday rentals in Leeward

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Leeward

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Guest favourite
A serene infinity pool overlooks the vibrant turquoise waters of the Caribbean. Surrounding the pool area, various coastal plants and rocks add to the natural ambience, while distant horizons and fluffy clouds create a peaceful setting.
Guest house in Long bay
4.93 out of 5 average rating, 92 reviews

VillaKendara~10%Off 5/23-30~Beach~Privat~Gate~View

Private~Gated~Beachfront~Convenient~Panoramic Water Views~Beautiful by Nature~A+ Sunrises/Sunsets~Swim in Pool or Sea, Snorkel~5 min to Grace Bay Hub & Beaches, Restaurants, Stores, Marina~Exclusive "Johnson Guide to Provo"~Fully Equipped with GMT Kitchen, Amenities, Supplies, AC, Fans, Wi-Fi, TV, DVD, Phone, Safe & LOFT FOR KIDS~CoralStone Deck, Pergola for Shade, BBQ~Snorkel Gear, Portable Beach Chairs & Umbrella~Island Partner Discount for Car Rental, Water Sports/Eco-Tours, Cruise, Massages

Guest favourite
A bright dining area overlooks the marina, featuring a table with chairs positioned for scenic views. Lush greenery frames the outdoor space, while the tranquil blue water reflects the clear sky. The room is designed with floor-to-ceiling glass doors that enhance the open layout.
Flat in Venetian Road Settlement
4.94 out of 5 average rating, 118 reviews

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.

Guest favourite
A serene view of the private Infiniti pool reflects the surrounding turquoise waters. Two lounge chairs are positioned on a textured surface, framed by a draped canopy that offers shade and relaxation. The tranquil landscape of Chalk Sound completes the peaceful atmosphere.
Flat in Providenciales
4.9 out of 5 average rating, 207 reviews

Beautiful Sunset Villa with Infiniti Pool

Beautiful Sunset Villa is nestled in the heart of Chalk Sound, Providenciales where guests are guaranteed a home away from home experience. It enjoys unique trade winds in a private and safe community close to restaurants and the beach. Beautiful Sunset Villa provides views of the famous Chalk Sound turquoise waters, featuring a private Infiniti pool, extensive pool deck, a dedicate kitchen and dining area with full air conditioning. View the video below! https://youtu.be/13YyhYECZQA

Top guest favourite
A spacious living area is seen with comfortable seating arrangements, including a large sofa and armchairs. Natural light floods in through sliding glass doors that lead to a patio. A flat-screen TV is positioned on the wall, complemented by a welcoming décor.
Apartment in Providenciales
4.95 out of 5 average rating, 108 reviews

The Yacht Club-Relaxed Vibe-1 BR-Pool-Beach

This spacious, comfortable, well-designed one-bedroom poolside apartment is in a private gated community—The Yacht Club. Couples and small families will appreciate the gorgeous grounds, stunning multi-level saltwater pool, relaxed vibe, and local restaurants. A five-minute walk will take you to one of the best beaches on the island, which features a snorkeling reef. The property is next to one of the largest marinas on the island with boat cruises, fishing & a variety of water sports.

Guest favourite
A view from the property shows a sandy area beside a quiet road that leads to the beach. Green foliage and tall pine-like trees frame the scene, with the sparkling blue ocean visible in the distance under a clear sky.
Flat in Providenciales
4.93 out of 5 average rating, 106 reviews

Pelican View #1 ground floor beachfront apartment

Pelican View apartments offer unrivalled beach access and a truly unique and tranquil way to experience Providenciales. Located in the neighbourhood of Blue Hills you’ll quickly be lulled into the local rhythm of island life as you sit on your ground floor terrace enjoying the spectacular views, listening to the waves crashing on shore, and planning which amazing local restaurant to enjoy for dinner. Watch the pelicans flying low across the water and the Osprey surveying his beach.

Guest favourite
Villa in Caicos Islands
5 out of 5 average rating, 8 reviews

Waterfront Villa &Pool - Cotton House-Sups -Kayak

Classic Caribbean 4 Bedroom canal front villa in Leeward. Cotton House has been designed in the timeless, traditional Caribbean aesthetic and is solar powered. Located in the prestigious gated Leeward community, this canal front home exudes an easy living elegance. Each of the four bedrooms opens to a central courtyard, the serene heart of the home featuring fountain, ferns, climbing vines, and tropical trees. *Ask us about our 3 Bedroom or 5 Bedroom options with this villa.

Top guest favourite
An outdoor area features a swimming pool bordered by sun loungers and a shaded seating area. Umbrellas provide shade, while lush greenery and ocean views create a serene environment. The clear water of the pool reflects the blue sky, enhancing the inviting space.
Villa in Providenciales
4.99 out of 5 average rating, 123 reviews

Villa DelEvan 4B / 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.

Top guest favourite
An infinity edge pool is visible on a spacious deck, overlooking stunning views of Juba Sound. The sunset casts warm hues across the sky, reflecting on the calm waters below. Lush greenery surrounds the area, enhancing the natural beauty of the landscape.
Guest house in Long Bay Hills
4.99 out of 5 average rating, 196 reviews

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.

Top guest favourite
Guest suite in Providenciales
5 out of 5 average rating, 106 reviews

"Captain's Quarters" Suite with a View!, King Bed

Captain’s Quarters is a newly renovated guest suite attached to our home, overlooking the Thompson Cove canal and within a 3 minute walk to the beach. You will enjoy your own private entrance, private terrace and private deck overlooking the canal. You are welcome to use our SUPs and kayaks, which are located on our guest dock. Book today for an ideal tropical escape to a tranquil area in Provo, TCI!

Guest favourite
The image captures a serene pool area surrounded by vibrant palm trees and blooming flowers. The tranquil water of the pool reflects the bright blue sky, while a view of the marina and boats is visible in the background, enhancing the relaxing atmosphere of the space.
Apartment in Providenciales
4.89 out of 5 average rating, 142 reviews

Romantic Escape with Stunning Pools & Sunset Views

Welcome to our private island paradise. This is a light, charming, one bedroom unit in a quiet setting with a view over the terraced pools & into Turtle Cove & the marina. Its 1091 square feet bring a spacious open plan living/dining/kitchen/balcony. The patio door opening spans 16 ft. The large bedroom has a king bed, walk-in closet, another TV & beautiful ensuite bath w/ large shower.

Guest favourite
A two-story house is framed by lush palm trees, showcasing a mix of wooden slats and open spaces. The expansive balcony extends over the entrance, while large glass doors invite natural light into the living area. Vibrant plants add a touch of greenery to the surroundings.
Villa in Providenciales
4.93 out of 5 average rating, 270 reviews

Spacious contemporary private villa

This beautiful and well appointed property was constructed in 2011. It has contemporary appliances, over 1400sq/ft of internal space with high '"loft" ceilings along with two large external deck areas and a private garden / yard. Located in walking distance to the main supermarket and gracebay west beaches (Bight Park), it makes the perfect island getaway.

Guest favourite
A dining area is set on a wooden deck, featuring a white table surrounded by light blue cushioned chairs. A large blue umbrella provides shade while the scenic view of the turquoise water and lush greenery is visible in the background.
Villa in Providenciales
4.95 out of 5 average rating, 122 reviews

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!

Popular amenities for waterfront rentals in Leeward

Quick stats about waterfront rentals in Leeward

  • Total holiday rentals

    Explore 70 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at £155 per night before taxes and fees

  • Verified guest reviews

    Over 1,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Leeward holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Leeward rentals

  • 4.9 Average rating

    Leeward stays are highly rated by guests – averaging 4.9 out of 5!