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 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, 88 reviews

Villa Kendara~BK 1/10-17~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

Guest favorite
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

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 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, 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.

Guest favorite
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, 35 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!

Top guest favorite
A beach bag with striped patterns and the word 'beach' is hung on a wooden structure. In the background, a sandy shoreline meets calm waters under a partly cloudy sky, with sun umbrellas visible along the beach.
Apartment in Wheeland Settlement
5 out of 5 average rating, 8 reviews

Caicos Dreams - 1 king bedroom, Large TV+ more

Caicos Dreams -100% renovated . Amazing!!. 1 Bedroom King Suite A 565sq perfectly formed condo is ideal for a couple looking to enjoy some peace and quiet whilst enjoying the delights of a recently renovated unit. Our Patio offers pool and ocean views that are simply amazing - plus we have a high-top comfortable outside table - perfect for watching the world go by and the sunsets - 1 min 34 seconds from door to sand - where you will find chairs, loungers, and shades for all.

Top guest favorite
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.

Superhost
Villa in Providenciales and West Caicos
4.85 out of 5 average rating, 144 reviews

Secluded 3 BR Villa on Taylor Bay -Place De La Sol

The luxury of privacy is what this villa is all about. A few steps through a private tropical path takes you to the pristine waters and powder sand beach that is Taylor Bay. This Villa is split between the main villa which hosts 2 bedrooms, living room, bathroom and kitchen/dining. The primary suite is located across the patio with it's private bathroom and outdoor/indoor shower. Sunsets on Taylor Bay are the best on the island! **12% TCI Tax Included

Luxe
An infinity pool surrounded by a stone deck is depicted, with a sunbed positioned nearby. Lush greenery frames the area, and wooden seating can be seen under a pergola. A view of the tranquil ocean and sky filled with clouds is visible in the background.
Villa in Grace Bay
4.89 out of 5 average rating, 9 reviews

Beach Shack

Follow the wood-deck down to your own slice of Grace Bay Beach at this Bohemian-beach house in Turks and Caicos. Celebrate your honeymoon in a minimalistic setting, only decorated with high-end furnishings and original works of art. Spend your afternoons lounging by the pool or splashing around in the sea. Later, walk over to Turtle Cove Marina and have dinner at one of their seafront restaurants. Copyright © Luxury Retreats. All rights reserved.

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 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.
Condo 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 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 $270 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!

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