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Waterfront vacation 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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Top guest favorite
A small weathered boat is anchored gently in shallow water, positioned along a sandy beach. The clear turquoise sea stretches towards a blue sky with a few wispy clouds, creating a serene coastal scene.
Apartment in Providenciales
4.94 out of 5 average rating, 115 reviews

Pelican View #3 unrivalled beach views

Pelican View apartments offers unrivalled beach access and a truly unique and tranquil way to experience Providenciales. Located in Blue Hills you’ll quickly be lulled into the local rhythm of island life as you sit on your 2nd floor terrace enjoying the spectacular views and listening to the waves crashing on shore. This 2-bed, 1-ba apartment is comfortably appointed with true up-cycled charm. Peppered throughout are some treasured vintage pieces to make it feel like your home away from home.

Guest favorite
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.
Apartment in Long bay
4.93 out of 5 average rating, 89 reviews

VillaKendara ~ BK3/28-4/4 ~ SeaFront ~ Private ~ 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 favorite
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.
Apartment in Venetian Road Settlement
4.94 out of 5 average rating, 117 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 favorite
An inviting outdoor area showcases a natural-shaped pool with a heated spa, surrounded by tropical landscaping. The open design features ample seating areas, dining spaces, and large sliding doors that provide a view of the main house and patio.
Villa in Leeward Settlement
4.98 out of 5 average rating, 50 reviews

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

*Great for couples and families - Pool - Heated SPA - On the canal - Sups - 5 min to the beach* Piccolo Ponte is an elegant 3 bedroom canal front Caribbean property that sits on an acre of private tropical garden where friends and family gather together to relax and enjoy a laid-back vacation island-style. Located directly on the clear and turquoise canals of the prestigious Leeward Settlement, just a few minutes away from Blue Haven Marina and many beach accesses and watersports operators.

Guest favorite
A thatched-roof gazebo is positioned near the water, surrounded by sandy ground and lush vegetation. Palm trees sway gently, and a calm body of water is visible in the background, reflecting the bright blue sky with fluffy clouds.
Loft in Long Bay Hills
4.88 out of 5 average rating, 189 reviews

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!

Guest favorite
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.
Apartment in Providenciales
4.91 out of 5 average rating, 198 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 favorite
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.
Condo in Providenciales
4.95 out of 5 average rating, 104 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.

Top guest favorite
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales
4.99 out of 5 average rating, 122 reviews

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.

Top guest favorite
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.
Guesthouse in Long Bay Hills
4.99 out of 5 average rating, 188 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.

Guest favorite
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.
Condo in Providenciales
4.89 out of 5 average rating, 138 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. Please note, elevator is currently under repair.

Top guest favorite
Guest suite in Providenciales
5 out of 5 average rating, 101 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 favorite
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, 265 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.

Popular amenities for Leeward waterfront rentals

Quick stats about waterfront rentals in Leeward

  • Total vacation rentals

    Explore 70 vacation rentals in Leeward

  • Nightly prices starting at

    Leeward vacation rentals start at G$43,937 GYD per night before taxes and fees

  • Verified guest reviews

    Over 990 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Leeward vacation rentals include wi-fi 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!