Beachfront holiday rentals in Leeward

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Leeward

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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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.
Flat in Long bay
4.94 out of 5 average rating, 88 reviews

VillaKendara~SeaFront~Gated~Private~Panoramic 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 serene beach scene features soft white sand leading to calm waters, with lounge chairs placed under umbrellas. The tranquil sky displays a gradient of pastel colors as the sun sets, illuminating the nearby condominium and surrounding palm trees.
Apartment in Wheeland Settlement
4.92 out of 5 average rating, 128 reviews

Holiday discount- 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). New refrigerator, sofa, tables, and new TV added October 2025!

Top guest favourite
An outdoor pool area is surrounded by a modern villa, featuring multiple lounge chairs positioned by the pool. At sunset, soft lighting enhances the ambience, while large glass doors lead to the interior living and dining areas. Lush greenery borders the space, providing an inviting atmosphere.
Flat in Long Bay Hills
5 out of 5 average rating, 6 reviews

Discounted Rates Luxury Private Full 1BR Suite 2

- Stay in one of our Private Newly Built Modern Suite on Long Bay Beach. -Your Private suite includes a fully equipped Kitchen, amazing living area with queen sofa bed and Smart TV, A king bed room, Fully equipped Bathroom and laundry with washer & dryer, central air conditioning & complimentary WIFI. - Fully gated in a safe high-end beach community. - Special promo discounts on local tours and activities. - Enjoy our large shared pool. hammock, Chess & Corn hole games & outdoor rain shower.

Superhost
Apartment in Wheeland Settlement
4.93 out of 5 average rating, 28 reviews

Ocean and Pool Front 2 king beds 2 Bath Condo

2nd floor , 2 bed, 2 bath, sleeper sofa, fully stocked kitchen, with a washer and dryer in the unit. 6 beach towels, beach chairs , & a cooler for your convenience. It has unimpeded views of both the ocean and the pool area from the comfort of your patio. Everything that TCI has to offer including restaurants, Grace Bay, shopping, water sport such as scuba diving, jet skiing and much more are with in a 10-20 minute drive from Northwest Point Resort. We do highly recommend that you rent a car.

Top guest favourite
Several beach chairs are positioned along the white sandy shore, each with a large umbrella providing shade. The turquoise waters of Grace Bay are visible in the background, scattered with people enjoying the beach and water activities.
Apartment in Providenciales
5 out of 5 average rating, 67 reviews

Beachy Chic / Grace Bay / Grandview on Grace Bay

Voted #1 Beach Destination in the World! We are located directly in the Heart of Grace Bay Beach...Location, Location, Location! With only 18 Beach Front units , you have privacy, location, and convenience. The "Grandview on Grace Bay" is an all Beach Front resort located directly on Grace Bay Beach, and included as one of the most beautifully placed properties on the island. Beach chairs are located at the pool and beach for your convenience, and placed out for you each day! Enjoy!

Top guest favourite
A bright and airy living space features a white sofa adorned with patterned pillows. Natural light filters in through large sliding glass doors that open to a private outdoor area, where a dining set awaits amid lush greenery.
Holiday home in Long Bay Hills
5 out of 5 average rating, 11 reviews

1BR Beach Suite w Pool Jacuzzi Kiteboarding K3

Esencia sits directly on Long Bay. This quiet and rural area has three miles of open white sand beach and sparkling clear turquoise water. It is ideal for the person who wants to be close to nature and seeks peace, quiet and natural beauty. This is the ‘wild’ side of Provo - natural, undeveloped, and simply close to nature and the sea. Here the beach is wide and flat with pure white sand. Our many palm trees provide shade and beauty and add to the feeling of privacy and naturalness.

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, 118 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.

Guest favourite
The image captures a luxury resort featuring a long, rectangular pool surrounded by lush greenery and palm trees. Sun loungers with umbrellas are positioned along the pool's edge, offering a relaxing space. The backdrop showcases the azure sea under a clear blue sky.
Apartment in Providenciales
5 out of 5 average rating, 24 reviews

Luxury Condo Somerset on Grace Bay!

Ocean Aria Residence-luxury condo at the exclusive Somerset Resort on Grace Bay. Open concept style living/dining area, spacious master bedroom with king bed, walk in closet and en suite bath.The second bedroom is located on the lower level with two twin beds and cozy sitting area. Condo's 2nd bathroom is located on the upper level. Queen size sofa bed in the living room can easily accommodate an extra guest.This is a ground floor unit and it has a view of a croquet lawn.

Guest favourite
An aerial view of the villa is presented, showcasing its modern structure alongside a clear turquoise sea. Lush greenery borders the property, and a pool is visible, framed by the vibrant landscape. The beach access is situated nearby, emphasizing the property's serene surroundings.
Villa in Providenciales
4.92 out of 5 average rating, 64 reviews

‘My Little Hideaway’ at Lucayan Cays

My Little Hideaway at Lucayan Cays offers exactly what you come to the beautiful islands of the Turks and Caicos for; Relaxation and Beauty. You are greeted every morning with a lovely sea view and a spectacular water access. If a stylish, modern but tropical getaway is what you are looking for ‘My Little Hideaway’ offers just that and so much more! So come and book at this beautiful hidden treasure and you’ll sure to come back again!

Guest favourite
A spacious balcony offers views of palm trees and vibrant blue umbrellas, surrounding two swimming pools. Lush gardens add greenery to the scene, while a comfortable chair is positioned nearby for relaxing moments.
Apartment in Turtle Cove
4.95 out of 5 average rating, 86 reviews

Queen Angel Condo with Pool and Ocean View

Our condo which is peaceful and centrally located offers breathtaking ocean views and splendid sunsets over the Turtle Cove Marina. The resort consists of luxurious gardens, two pristine swimming pools, private outdoor spaces, balconies and free shared parking. A short five minute walk brings you to unbeatable snorkeling at the beautiful Smith's Reef on Gracebay, frequently rated as the best beach in the world.

Guest favourite
An outdoor patio area features a circular table surrounded by four chairs, providing a space for relaxation. Colorful potted plants and shells decorate the surrounding walls, enhanced by the backdrop of vibrant blue accents on the building. A shaded roof offers protection from the sun.
Flat in Providenciales
4.92 out of 5 average rating, 86 reviews

Beachfront Rental Beach Hut Unit 1

Welcome to the Beach in Beautiful Blue Hills! Imagine yourself on 400 ft. of pristine beach located beside the world famous Conch Shack. You are close to grocery stores, restaurants and you are on the Ocean. The Beach Hut offers great snorkeling, and a beautiful clean and quiet beach to relax and unwind!

Guest favourite
A balcony is furnished with a glass-top table and dark wicker chairs, offering views of gently swaying palm trees and the ocean in the background. The serene landscape includes a grassy area leading to the beach, illuminated by natural sunlight.
Apartment in Wheeland Settlement
4.74 out of 5 average rating, 34 reviews

Stunning one bdrm ocean front views-pool, hot tub

This newly upgraded ocean front condo is located at northwest point resort, with new italian marble floors and countertops offers guests stunning views of the ocean and pool, spacious, large bedroom kitchen and bathroom will provide lot's of space with a balcony.

Popular amenities for beachfront rentals in Leeward

Quick stats about beachfront rentals in Leeward

  • Total holiday rentals

    Explore 20 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at $349 SGD per night before taxes and fees

  • Verified guest reviews

    Over 200 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    20 properties feature pools

  • Wifi availability

    20 of Leeward holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Leeward rentals

  • 5 Average rating

    Leeward stays are highly rated by guests – averaging 5 out of 5!