Beachfront vacation rentals in Leeward

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Top-rated beachfront rentals in Leeward

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

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Guest favorite
A scenic oceanfront view showcases a sandy beach lined with sun loungers and umbrellas. Lush greenery borders the beach, while the clear sky and gentle waves complete the tranquil setting. In the distance, beachside buildings can be seen against the horizon.
Condo in The Bight Settlement
4.96 out of 5 average rating, 114 reviews

Coral Condo on Grace Bay Beach

• Gorgeous 1 bedroom oceanfront condo on the top floor of Coral Gardens on Grace Bay Beach • Stunning ocean view • Relaxed, modern coastal decor • Newly renovated, fully appointed kitchen & stainless steel appliances • Centrally located with world-renowned snorkeling & water sport activities • 2 pools • Complimentary Beach chairs & towels • High Speed Internet/Cable, SmartTV • Direct Beach access, close walk to Wymara Resort, West Bay Club, Beach House, & Windsong • Somewhere Cafe Restaurant.

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.
Apartment in Long bay
4.94 out of 5 average rating, 87 reviews

Villa Kendara~SALE NOV-DEC~BeachFront~Private~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

Top guest favorite
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.
Apartment in Long Bay Hills
5 out of 5 average rating, 5 reviews

Discounted Rates Luxury Private Full 1BR Suite

- 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
A bright living space displays a dining table with dark wood and plush seating. In the background, expansive glass doors frame a stunning view of turquoise waters and lush landscapes. A potted floral arrangement adds a touch of color to the serene setting.
Home in Providenciales
4.96 out of 5 average rating, 48 reviews

Coastal Vibes Villa Near Sapodilla Beach

Coastal Vibes Villa offers a unique vacation experience for families and couples. The sprawling two dwelling villa is located on Chalk Sound National Park with stunning views of the water. A private pool with expansive decking and patio provides many areas to "chill". Watercraft provided allows for everyone to explore Chalk Sound. Renowned Sapodilla Bay beach is conveniently located across the street. 2 min walk! Secluded and quiet Taylor Bay beach is located up the street. 2 min drive!

Top guest favorite
A shimmering pool with a clear blue surface reflects the sky, surrounded by green tropical plants and potted decorations. A wooden path leads toward a beach area, with lounge chairs and umbrellas visible in the distance, framed by palm trees under a bright sky.
Condo in Grace Bay
5 out of 5 average rating, 34 reviews

Luxury Grace Bay Beachfront - Perfection!

Located beachfront and wonderfully situated on 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 located at the pool and beach for your convenience, and placed out for you each day. Close to amenities and restaurants!

Guest favorite
A private balcony is furnished with two woven lounge chairs facing a scenic view of the ocean and resort pool area. The surrounding landscape features green foliage and white buildings, creating a tranquil atmosphere for relaxation outdoors.
Condo in The Bight Settlement
4.87 out of 5 average rating, 67 reviews

Ocean view paradise

Welcome to paradise! Imagine waking up every morning to this incredible ocean view at La Vista Azul! Our studio unit has a queen size bed, full kitchen, and walk-in shower in the bathroom.Enjoy a 5 minute walk to the beach or hang out at the pools or hot tub down stairs. Covered parking below the building has an elevator that conveniently takes you right to our door. Check-in is a breeze with our keyless lock system. Best for 1-2 adults but the sleeper sofa allows for up to 2 children.

Superhost
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.
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). New refrigerator and new TV added October 2025!

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
4.95 out of 5 average rating, 124 reviews

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 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 favorite
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 favorite
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.
Condo 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 favorite
A comfortable living area features plush seating arranged around a coffee table. A television is mounted on a stand, and light flows in through large glass doors, which open to a patio area. A ceiling fan enhances the open atmosphere.
Condo in Grace Bay
4.94 out of 5 average rating, 66 reviews

Splendid condo walks out to Grace Bay Beach

Well appointed two bedroom condo with direct access to the most beautiful beach in the world. Quiet 18 unit condominium complex without hustle and bustle of a resort. Close to restaurants, groceries, and shopping. My place is good for couples, solo adventurers, business travelers, and families (with kids). Local taxes are included in the rental rates.

Guest favorite
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.
Apartment in Providenciales
4.92 out of 5 average rating, 85 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!

Popular amenities for Leeward beachfront rentals

Quick stats about beachfront rentals in Leeward

  • Total vacation rentals

    Explore 20 vacation rentals in Leeward

  • Nightly prices starting at

    Leeward vacation rentals start at ﺩ.ﺇ992 per night before taxes and fees

  • Verified guest reviews

    Over 200 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    20 properties feature pools

  • Wi-Fi availability

    20 of Leeward vacation rentals include wi-fi 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!