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.

1 of 1 pages1 / 1
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
4.94 out of 5 average rating, 95 reviews

VillaKendara~8/8-Sep@20%OFF~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, 119 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
Villa in The Bight Settlement
5 out of 5 average rating, 11 reviews

Townhome Villa – Steps to Grace Bay (Sleeps 4)

Escape to your own luxurious villa in Grace Bay! This spacious 2-bedroom, 2.5-bath retreat sleeps 4 and features a full kitchen, large living area, washer/dryer, SMART TVs, and private patios and balconies. Enjoy resort-style amenities including hotel check-in, concierge service, on-site gym, saltwater pool, complimentary bikes, and beach shuttle. Just steps from Grace Bay Beach, shops, cafés, and restaurants—perfect for families, friends, or groups seeking privacy and comfort in paradise.

Top guest favourite
The spacious bedroom features a king-size bed with striped bedding and a decorative pillow. A wall-mounted Smart TV is positioned across from a wooden desk and chair. Large sliding doors lead to a balcony, allowing natural light to illuminate the room, which has a vibrant blue floor design.
Guest house in Providenciales
5 out of 5 average rating, 116 reviews

“Sail Loft Port”, Duplex with a Pool, Beach Access

Sail Loft Port is the left side of our purpose-built guest duplex. Our Sail Loft duplex features two separate but identical efficiency suites, each one equipped with a King Sized bed, bath and kitchenette. The pool is shared with guests who may be staying in the other side. Wander down to the dock and use our SUPs and kayaks in the canal where you are guaranteed to see turtles. Fast WiFi lets you work from home if you must. Smart TVs with Netflix help you wind down after a day of fun.

Superhost
Villa in Leeward Settlement
5 out of 5 average rating, 3 reviews

Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks

Classic Caribbean 3 Bedroom canal front villa in Leeward. Cotton House has been designed in the timeless, traditional Caribbean aesthetic and is solar powered. Located in the gated Leeward community (25 min from PLS airport - 8 min to Grace Bay), this canal front home exudes an easy living elegance. Each bedroom opens to a central courtyard, the serene heart of the home featuring fountain, ferns, climbing vines, and tropical trees. *Ask us about our 4 and 5 Bedroom options for this villa.

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, 211 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
4.96 out of 5 average rating, 113 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
4.94 out of 5 average rating, 110 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.

Top guest favourite
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, 132 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 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, 198 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 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, 273 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 wooden staircase is visible, leading down towards a calm lagoon. Lush greenery surrounds the steps, providing a serene backdrop. The water reflects a light turquoise hue, hinting at the scenic beauty of Chalk Sound. Clear skies with a few clouds create a bright atmosphere.
Flat in Providenciales
4.77 out of 5 average rating, 154 reviews

Serene Lagoonfront Stay Near Sapodilla Bay

- Enjoy serene views of Chalk Sound and the beautiful Atlantic horizon. - Minutes from pristine beaches, perfect for sunbathing and swimming. - Easy access to vibrant eateries and adventurous water sports. - Comfortable and well-equipped space ready for your arrival. - Secure your peaceful getaway and book your stay with us today!

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 £158 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!