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

Apartment in Providenciales

4.93 out of 5 average rating, 104 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.

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Apartment in Long bay

4.94 out of 5 average rating, 86 reviews

Villa Kendara~50%~ 9/20-10/4~SeaFront~Private~View

Private~Gated~Seafront~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 Discounts for Car Rental, Water Sports/Eco-Tours, Cruise, Massages

Guest favorite

Apartment in Venetian Road Settlement

4.94 out of 5 average rating, 115 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 favorite

Villa in Leeward Settlement

4.98 out of 5 average rating, 45 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

Loft in Long Bay Hills

4.88 out of 5 average rating, 178 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!

Superhost

Apartment in Providenciales

4.9 out of 5 average rating, 187 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

Guest favorite

Villa in Providenciales

4.99 out of 5 average rating, 112 reviews

Villa DelEvan 4B / 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 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.

Superhost

Condo in Providenciales

4.89 out of 5 average rating, 129 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 where you will particularly appreciate the new Bosch appliances. The patio door opening spans 16 feet. The large bedroom has a king size bed, walk-in closet, another TV, & a beautiful ensuite bath w/ a roomy walk-in shower.

Top guest favorite

Guesthouse in Long Bay Hills

4.99 out of 5 average rating, 177 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.

Superhost

Apartment in Caicos Islands

4.84 out of 5 average rating, 148 reviews

Palm Point Loft - Waterfront Canal

Palm Point Loft is the perfect spot for your family to come and experience the peace and beauty of Providenciales. Located canal side, this private and spacious 2 bedroom second floor apartment is centrally located, 5 mins to Grace Bay Beach, restaurants and grocery stores. The unit is airy and bright offering a private sanctuary for guests to relax on their own balcony - the perfect place to unwind and enjoy the gentle breeze off the water while watching the sunset.

Superhost

Condo in Wheeland Settlement

4.92 out of 5 average rating, 128 reviews

Couple’s Retreat - ocean view, pool and hot tub!

Free cancellation! Oceanside oasis with pool, ocean and garden views. Escape to the pristine blue waters at Northwest Point. Pool, ocean and hot tub within steps of condominium. Free access to kayaks and SUPs, snorkel gear, owners beach chairs, loungers and miles of secluded beach for walking, exploring or beachcombing. Airport is appoximately a 15 minute drive from Northwest Point Condominiums (formerly Northwest Point Resort).

Top guest favorite

Home in TC

4.98 out of 5 average rating, 187 reviews

“The Lighthouse”, Private Pool, Ocean Views, Beach

The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!