Apartment holiday rentals in Leeward

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Top-rated apartment rentals in Leeward

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Guest favourite
Flat in Leeward Settlement
5 out of 5 average rating, 12 reviews

15 mins walk to restaurants and beach

Welcome to Peaceful Hideaway—your serene escape designed for rest and renewal. Step into a calming space equipped with air conditioning, Wi-Fi, a cozy bed, and kitchen to make you feel instantly at home. Just moments away, you’ll discover the breathtaking turquoise waters of Grace Bay Beach. With restaurants, grocery stores & nightlife all within easy reach, convenience meets tranquility here. I’m truly delighted to host you and hope your stay is as relaxing and memorable as the island itself.

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, 118 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.

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, 15 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.

Top guest favourite
A well-furnished room features a spacious bed and two comfortable seating chairs. A round table holds a bowl of fresh fruit. Vibrant artwork and colorful cushions accent the walls and seating area, creating a lively atmosphere. Light streams in from a nearby window.
Flat in Long Bay Hills
5 out of 5 average rating, 111 reviews

Jade@Long Bay Retreat-Luxury Stay near Grace Bay

LONGBAYRETREAT redefines luxury holiday rentals. Long Bay Retreat is developed and run by ex-hoteliers from luxury hotel chains like Four Seasons, Raffles, Six Senses, and Taj Hotels. Nestled near Long Bay and Grace Bay beaches, it offers the perfect blend of tranquility & vibrance. Upscale locality, stunning Infiniti pool, tastefully crafted spaces enhanced by Balinese Teak furniture, kitchenette, high-speed internet, and finest bed-bathroom linen sets this place apart from the ordinary.

Top guest favourite
A contemporary living area features a sleek white sectional sofa with plush cushions, positioned around a minimalist coffee table. Decorative pillows and a small vase with flowers add subtle color. Soft natural light brightens the space, enhancing the modern design.
Flat in Leeward Settlement
5 out of 5 average rating, 115 reviews

Luxury Spacious 1 Bed Condo close to the Beach

Just renovated: The perfect condo, and only 3 minutes from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. This 925 sqft luxury 1 bedroom, freshly renovated (Jan 2023), provides all necessary amenities for your home away from home.

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
4.9 out of 5 average rating, 209 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 panoramic view captures the ocean on the horizon, framed by swaying palm trees. The foreground features a spacious terrace with blue umbrellas providing shade. Below, a row of white-roofed buildings is nestled among lush greenery, enhancing the serene coastal atmosphere.
Flat in Providenciales and West Caicos
4.95 out of 5 average rating, 219 reviews

☀️🏖 Modern Luxury Ocean View Studio Suite 🏝☀️

☀️🏖 NEWLY RENOVATED, SPACIOUS STUDIO with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the studio is close to several excellent restaurants, cafes, bars, a casino, and a marina. Most notably, the studio is a 10 minute walks to Smith's Reef in the Princess Alexandra Park National beach. Smith’s Reef is located near Turtle Cove on the north coast of Providenciales, and about 3.5 miles (5.6 km) from Grace Bay ☀️🏖

Superhost
The property features a two-story structure with white walls and a sloping roof, surrounded by palm trees and lush green grass. The building is situated along a tranquil canal, reflecting the clear blue sky dotted with fluffy clouds.
Flat in Caicos Islands
4.84 out of 5 average rating, 158 reviews

Palm Point Loft-Waterfront Canal (NewlyRenovated)

Palm Point Loft is the perfect spot for your family to come and experience the peace and beauty of Providenciales. Located canal side, this newly renovated 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.

Guest favourite
A view from the property shows a sandy area beside a quiet road that leads to the beach. Green foliage and tall pine-like trees frame the scene, with the sparkling blue ocean visible in the distance under a clear sky.
Flat in Providenciales
4.94 out of 5 average rating, 109 reviews

Pelican View #1 ground floor beachfront apartment

Pelican View apartments offer unrivalled beach access and a truly unique and tranquil way to experience Providenciales. Located in the neighbourhood of Blue Hills you’ll quickly be lulled into the local rhythm of island life as you sit on your ground floor terrace enjoying the spectacular views, listening to the waves crashing on shore, and planning which amazing local restaurant to enjoy for dinner. Watch the pelicans flying low across the water and the Osprey surveying his beach.

Guest favourite
An aerial view captures the vibrant turquoise waters of Sapodilla Bay Beach, with calm waves gently lapping at the shore. Nearby, a wooden pier extends into the water, providing access to serene surroundings. The image includes markers indicating proximity to various local attractions.
Flat in Providenciales
4.86 out of 5 average rating, 250 reviews

Tatis Ferguson Villas 2

Our new Modern Studio Apartment awaits offering its warm and friendly hospitality to you. If your choice is comfort and service at a reasonable price, come and let us show you our care for your simple and most extravagant desire to enjoy a getaway with your significant other or a getaway for yourself. What are you waiting for ? The location is in South Dock Road, 5 mins from the airport, 10 from sapodilla bay beach, a few mins away from restaurants and right behind a supermarket.

Guest favourite
Flat in Leeward Settlement
4.96 out of 5 average rating, 28 reviews

Leeward Condo - Sleeps 4

Welcome to Palm Grove Villa! This beautifully decorated 1-bedroom, 1.5-bath condo in Leeward sleeps 4 and is a short stroll from Leeward and Grace Bay Beaches. Enjoy modern décor, a cozy king bedroom, and a queen pullout sofa in the open living area. The fully equipped kitchen and private patio/balcony make it ideal for relaxing. Amenities include a sparkling pool and grilling area. With nearby beaches, restaurants, and shops, this condo is the perfect island escape!

Top guest favourite
Flat in Providenciales
4.96 out of 5 average rating, 272 reviews

The Old Beach House 2 bedroom

We have two Garden apartments downstairs that we renovated. One two bedroom two bathroom, and one 1 bed 1 bathroom. Just a 3 minute walk from a white sandy beach. You can walk to Da Conch shack restaurant along the beach in 5-10 minutes. Off the beaten trail. We live upstairs with our our potcake Boxer. We are so sad to say we just lost our legend Buster who you would have read about in all of our reviews.

Popular amenities for Leeward apartment rentals

Quick stats about flat rentals in Leeward

  • Total holiday rentals

    Explore 40 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at $153 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,530 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

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Leeward holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Leeward rentals

  • 4.7 Average rating

    Leeward stays receive an average rating of 4.7 out of 5 from guests