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Waterfront holiday rentals in Leeward

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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 favourite
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.
Flat 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 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, 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.

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, 103 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.

Guest favourite
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.
Flat in Long Bay Hills
5 out of 5 average rating, 5 reviews

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.

Guest favourite
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 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
4.91 out of 5 average rating, 199 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, 105 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 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, 117 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, 191 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
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.
Apartment in Grace Bay
4.97 out of 5 average rating, 88 reviews

Luxe Home / 2 bedroom (5 minute walk to beach)

Large 1200 square feet / top floor oversized END UNIT condo sophisticated elegance in Grace Bay - 2 large bedrooms/ queen size beds, 2 full bathrooms. Thoughtful design - makes all the difference. Short walk to beach. Pool and parking onsite. 4 Beach chairs and beach umbrella included along with beach towels. Fitness room in development with bike machine, elliptical and treadmill - no free weights. 2 yoga mats in our condo. We do not provide bath soap and shampoo.

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, 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.

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, 267 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 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 $269 SGD per night before taxes and fees

  • Verified guest reviews

    Over 990 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 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!