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Holiday houses in Leeward

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Top-rated holiday rentals in Leeward

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Guest favourite
The image showcases a modern villa with a private pool in the foreground. Lounge chairs are arranged around the pool, while an outdoor dining area and BBQ are visible under a shaded structure. Large glass doors lead into the bright interior space.
Home in Leeward Settlement
4.94 out of 5 average rating, 18 reviews

Leeward Landing Villa

Escape to paradise at Beach Landing Villa nestled in the heart of Leeward TCI. This luxurious villa is just minutes away from the pristine award-winning Grace Bay Beach offering a perfect blend of relaxation and adventure. Conveniently cruise your community with the provided pedal bikes. Lounge in the backyard in your private pool or relax indoors with the brilliant large screened TV equipped with all the latest streaming services. Book your villa now for an unforgettable experience in paradise!

Guest favourite
An outdoor area features a private pool surrounded by lush indigenous foliage. Comfortable lounge chairs are positioned nearby, with colorful towels neatly arranged. The scene overlooks a serene landscape, enhancing the inviting atmosphere for relaxation and enjoyment.
Cottage in Long Bay Hills
4.94 out of 5 average rating, 109 reviews

Flame Tree Cottage|Ocean view&pool.Walk to beach

Built in 2013. 1 bedroom 2 bathroom cottage with PRIVATE POOL. Sunrise & ocean view from the front deck and only 1/4 mile to the beach. Perfect for 2, but can sleep up to 6. Full kitchen, 2 bathrooms + outdoor shower. No bathtub. Propane Grill. AC in master bedroom. WIFI throughout & local cell provided. This quaint clutter-free 1200 square foot home is surrounded by indigenous foliage, cactus', succulents and native stonework. A rental car is recommended to explore all the island has to offer!

Guest favourite
A bright and airy room features large windows allowing natural light to fill the space. A spacious bed adorned with floral accents is complemented by a cozy seating area. A television is mounted on a white cabinet, and a small plant adds green to the decor.
Apartment in Venetian Road Settlement
4.9 out of 5 average rating, 113 reviews

Cozy Studio Near Beaches w/ Gym & Pool Access

Welcome to your idyllic island retreat! Our centrally located unit offers the perfect blend of convenience and tranquility. Nestled at the heart of the island, you're just minutes away from pristine beaches, supermarkets, cultural hotspots and the airport. Unwind in our thoughtfully designed space, boasting island-inspired decor. Whether you seek adventure or relaxation, this rental is your gateway to a memorable island experience. Book now and make our home yours during your island getaway!

Guest favourite
The expansive resort pool area features multiple sections, including a large main pool with a central gazebo. Vibrant palm trees surround the space, enhancing the tropical atmosphere, while sun loungers and umbrellas are positioned nearby for guest relaxation.
Condo in Providenciales
4.92 out of 5 average rating, 248 reviews

★★★★★ Modern Condo | Amazing Pool | On Site Spa

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub (under consrtuction until mid-Nov) • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Guest favourite
A modern living area is presented with a spacious white sectional sofa, accented by decorative cushions. A sleek coffee table sits in the center, featuring a playful design. Wall art and a small plant add subtle touches to the minimalist decor.
Condo in Leeward Settlement
4.93 out of 5 average rating, 92 reviews

Luxury 1Bed Large ModernCondo, close to Grace Bay

The perfect large 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 sq. ft. luxury one bedroom, freshly renovated in Feb 2023, provides all necessary amenities for your home away from home.

Top Guest favourite
A rooftop terrace features multiple sun loungers and circular seating areas, complemented by blue umbrellas providing shade. The water of the pool reflects the sky above, creating a calming atmosphere. Lush greenery and distant rooftops are visible in the background, adding to the serene setting.
Condo in The Bight Settlement
4.95 out of 5 average rating, 112 reviews

Oasis | 1 BR Condo | Blue View | Pool & Wifi

Peaceful Palm Trees with a peek of Ocean View! 10 min walk to the beach or 10 min drive to Grace Bay. Located on 2nd floor of the higher buildings, this condo is a spacious studio with Queen Bed, full kitchen, living room, bathroom, washer and dryer, Wifi and free parking. The large balcony has a pretty view over soothing palm trees dancing in the breeze, with a peek at the ocean in the distance. A great place for morning coffee or relax after long day at the beach or by the pool.

Top Guest favourite
A serene outdoor space features a sparkling pool surrounded by lush tropical plants and palm trees. Soft lighting illuminates the area, enhancing the inviting atmosphere. A shaded lounge chair rests nearby, offering a comfortable spot to relax and enjoy the peaceful surroundings.
Apartment in Leeward Settlement
4.95 out of 5 average rating, 241 reviews

Romantic Apartment few steps from beach

Wake up to the soothing melody of a mockingbird in the garden, as gentle sunlight filters through the lush greenery. Sip your morning coffee on the balcony, overlooking the tropical garden and sparkling crystal-clear pool, where the peaceful ambiance sets the tone for a romantic escape. Afterward, take a leisurely stroll through the vibrant garden or wander just a few minutes to the nearest beach with turquoise waters and soft white sands, perfect for a tranquil start to your day.

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.
Apartment in Providenciales
4.88 out of 5 average rating, 218 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.

Top Guest favourite
A tranquil beach scene shows soft, sandy shores meeting clear turquoise waters under a partly cloudy sky. Gentle waves lap at the shoreline, while palm trees and distant structures provide a glimpse of the local environment. A wooden pier is visible in the background.
Apartment in Providenciales
4.99 out of 5 average rating, 102 reviews

Pelican View #4 amazing beach views

Pelican View apartments offers 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. From Blue Hills it’s an easy 15 minute drive east to the heart of the tourist mecca of Grace Bay; if you travel west you’ll find the best national parks and nature reserves that Turks & Caicos has to offer, often overlooked gems in this island paradise.

Superhost
A modern villa is showcased, with its sleek design complemented by lush tropical landscaping. A private plunge pool is visible, surrounded by wooden decking and lounge chairs. A small outdoor dining area and a barbecue grill are also present, creating a relaxing outdoor living space.
Villa in Long Bay Hills
4.92 out of 5 average rating, 129 reviews

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY

Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

Top Guest favourite
An airy studio features a king size bed adorned with a patterned comforter, complemented by hardwood flooring. A compact kitchen area with a small fridge, microwave, and stove is visible in the background. A flat-screen TV is mounted on the wall opposite a small dining table with blue chairs.
Guest suite in Leeward Settlement
4.95 out of 5 average rating, 82 reviews

Erisa Studio - cozy studio close to GraceBay Beach

Erisa Studio is a bright, comfortable studio with a king bed, high ceilings, AC, ceiling fan, 32" TV, and a large 3-door patio slider. It includes a small kitchen and a spacious bathroom. Just a 15-min walk or 3-min drive to Grace Bay Beach, shops, and restaurants. Next to Provo Golf Club and a short drive to Long Bay Beach. Beach towels, beach chairs, sunbrella and cooler provided. Bike rental available for $10/day, but we highly recommend a car. Private entrance.

Top Guest favourite
Guesthouse in Leeward Settlement
4.97 out of 5 average rating, 114 reviews

"The Nest Cozy Cottage"

“The Nest” Spacious and modern 1 bedroom cottage sits amongst a well-manicured garden with majestic swaying palms. Less than 150 steps away from the famous Grace Bay Beach. This cozy sanctuary is quiet and bears the true beauty of itself, it’s perfect for honeymooners or if you’re just seeking for some quiet and down time. Complete with high-speed internet, cable TV and all amenities one need for the perfect vacation, The Nest is where you want to be.

Popular amenities for Leeward holiday rentals

Quick stats about holiday rentals in Leeward

  • Total holiday rentals

    Explore 310 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at $156 NZD per night before taxes and fees

  • Verified guest reviews

    Over 6,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    230 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    260 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    310 of Leeward holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Leeward rentals

  • 4.8 Average rating

    Leeward stays are highly rated by guests—averaging 4.8 out of 5!