Waterfront vacation rentals in Leeward

Find and book unique waterfront rentals on Airbnb

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$43,933 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,220 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 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!

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 serene beachfront scene showcases two yellow lounge chairs positioned under white umbrellas. The calm turquoise waters are framed by a clear blue sky, with fluffy white clouds dotting the horizon. Native greenery and sandy pathways lead to the water's edge.
Villa in Providenciales

Villa DelEvan 4D / 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 distance to 4 restaurants. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated beachfront property, with a garden view, private parking, 24hr security. Beach is less than a 60sec walk. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

ViewBeachLaundry

4.96 out of 5 average rating, 155 reviews
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.
Guesthouse in Long bay

Villa Kendara~50% 9/26-10/3 ~Beach~Privt~Gate~View

Private~Gated~Beachfront~Convenient~Panoramic Water Views~Beautiful by Nature~A+ Sunrises/Sunsets~Pool~Snorkeling~5 min to Grace Bay Hub & Beaches, Dining, Stores, Marina~Exclusive "Johnson Guide to Provo"~Fully Equipped Gourmet Kitchen~Lots of Amenities/Supplies~AC, Fans, Wi-Fi, TV, DVD, Phone, Safe~LOFT FOR KIDS~CoralStone Deck (3 Seating Areas, Pergola for Shade)~BBQ~ Snorkel Gear~Portable Beach Chairs & Umbrella~Island Partner Discount for Car Rental, Water Sports/Eco-Tours, Cruise, Massages

ViewBeachValue

4.94 out of 5 average rating, 97 reviews
Top guest favorite
A covered balcony is furnished with two dark wicker chairs and a glass-top table. The panoramic view showcases the pool area with blue lounge chairs and the ocean beyond, framed by a clear sky with scattered clouds.
Apartment in The Bight Settlement

Stunnig Oceanview Studio w/ Balcony +Pools

This beautifully designed studio offers stunning views of the turquoise waters of Grace Bay, just a short walk away. Whether you're here to relax, or enjoy the island lifestyle, this space gives you the perfect balance of comfort and location. 🏝 The Space Private balcony with ocean views Queen bed + sofa bed Fully equipped kitchen Fast WiFi + Smart TV 🌴 Resort Amenities 2 swimming pools Lounge areas & sunbeds Free parking 📍 Location Grace Bay Beach:~10-minute walk Grace Bay area 7 min drive

ViewBeachDecor

4.99 out of 5 average rating, 104 reviews
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

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.

ViewRiverBackyard

4.94 out of 5 average rating, 121 reviews
Top guest favorite
An outdoor deck features a private pool surrounded by tropical foliage. Lounge chairs are positioned near a table shaded by a large umbrella. A view of beachside structures and palm trees can be seen in the background under a clear blue sky.
Apartment in Long Bay Hills

Apt with private pool and direct beach access

Discover an intimate oasis perched just steps from the turquoise waters of Long Bay. Our newly added Oceanfront One-Bedroom Apartment at Swaying Palms offers the perfect blend of privacy, luxury, and resort-style amenities—ideal for couples, solo travelers, or anyone craving a secluded tropical retreat. This space features a full kitchen, private pool & spacious outdoor deck overlooking the turquoise sea. Your very own private umbrella/lounge chairs will be placed daily at the water's edge.

BeachViewCleanliness

5.0 out of 5 average rating, 24 reviews
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

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.

ViewBeachCondition

4.98 out of 5 average rating, 54 reviews
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

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.

BeachViewAir conditioning

4.96 out of 5 average rating, 118 reviews
Superhost
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

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

ViewBeachTV

4.89 out of 5 average rating, 215 reviews
Top guest favorite
A tranquil beach scene shows soft, sandy shores meeting clear turquoise waters under a partly cloudy sky. Gentle waves lap at the shoreline, while palm trees and distant structures provide a glimpse of the local environment. A wooden pier is visible in the background.
Apartment in Providenciales

Pelican View #4 amazing beach views

Pelican View apartments offers 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. From Blue Hills it’s an easy 15 minute drive east to the heart of the tourist mecca of Grace Bay; if you travel west you’ll find the best national parks and nature reserves that Turks & Caicos has to offer, often overlooked gems in this island paradise.

ViewBeachCondition

4.98 out of 5 average rating, 138 reviews
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

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.

ViewRiverCheckout

5.0 out of 5 average rating, 200 reviews
Guest favorite
Home in Leeward

Channel Villa - Elegant Canal-Front Retreat

Welcome to Channel Villa, a beautifully refurbished four-bedroom canal-front retreat in the sought-after Leeward area, just moments from Blue Haven Marina & Resort. Designed for relaxed luxury and effortless island living, with a large covered patio, private swimming pool, and tropical landscaping that enhances privacy and tranquility. Channel Villa offers a serene waterfront atmosphere while remaining close to world-class beaches, dining and boating.

BeachFamilyPool

4.88 out of 5 average rating, 8 reviews
Top guest favorite
A central pool surrounded by lounge chairs reflects the bright blue sky above. Lush palm trees frame the area, creating a serene atmosphere. Modern white buildings with large windows stand on either side, providing a contemporary backdrop to this inviting space.
Condo in Grace Bay

Luxe Home / 2 bedroom (5 - 7 min walk to beach)

Large 1200 sq ft top‑floor oversized end unit condo with a modern / sophisticated design in the heart of Grace Bay. 2 large bedrooms with queen size beds and 2 full bathrooms. Short walk to Grace Bay Beach. Pool and secure parking onsite. We provide 4 beach chairs, 1 umbrella, beach towels, and beach cooler. Onsite gym equipped with a bike machine, elliptical, and treadmill (no free weights). Two yoga mats in condo

BeachViewTV

4.97 out of 5 average rating, 107 reviews

Popular amenities for Leeward waterfront rentals