Holiday houses in Leeward

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Leeward

  • Total holiday rentals

    Explore 330 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at $159 NZD per night before taxes and fees

  • Verified guest reviews

    Over 7,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    240 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    280 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    330 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!

Top-rated holiday rentals in Leeward

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

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Top Guest favourite
Villa in Grace Bay
4.96 out of 5 average rating, 77 reviews

Ideal Honeymoon Villa

Luxurious Gated Villa near Grace Bay Beach– Private Pool & Jacuzzi♨️ Escape to this luxury villa, just 2 minutes by car or a 10-min walk from Grace Bay Beach. Relax in your private infinity pool or rooftop jacuzzi with ocean view. The villa features 2 outdoor balconies, a modern kitchen with new appliances, and fast fiber internet. Perfect for 2 guests, this private retreat offers comfort, style, and Super host service. Close to dining, shopping, and activities. Book your dream vacation today🌴

Top Guest favourite
A charming home is surrounded by lush palm trees and vibrant tropical landscaping. The exterior features a combination of stucco walls and a tiled roof under a clear blue sky. A gravel path leads to the entrance, adding to the welcoming ambiance.
Home in Grace Bay
4.91 out of 5 average rating, 123 reviews

Tropical Carabas Villa!

Peaceful Villa Near Grace Bay Beach 🌴 Escape to this serene villa just minutes from Grace Bay Beach and steps from Coco Bistro. Enjoy a private pool, air-conditioned bedrooms, a fully equipped kitchen, and an outdoor grill for relaxing meals. Lounge with beach towels and chairs, stay connected with strong Wi-Fi, and soak in the lush tropical surroundings. The perfect mix of comfort, convenience, and tranquility for your getaway! 🌴 12% government tax is included in the listed price.

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
4.96 out of 5 average rating, 263 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.

Top Guest favourite
A picturesque entrance leads to a light blue house surrounded by lush tropical vegetation. A smooth driveway, lined with palm trees and native plants, leads up to the home, providing a sense of privacy and tranquility. The clear sky enhances the inviting atmosphere.
Home in Leeward Settlement
4.96 out of 5 average rating, 97 reviews

PERIWINKLE | Charming Island Home|Near to Beach

Nestled in the Gated Upscale community of Leeward at the end of a quiet cul-de-sac is Periwinkle. Experience the true flavor of the Islands with us. Be cradled and relax in the lush native vegetation and enjoy the view from the many windows which decorate the home. Periwinkle is a short stroll away from the magnificent soul quenching Leeward Beach and a five minute drive to the heart of Grace Bay for great shopping and dining experiences. Escape to the quieter side of 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
4.9 out of 5 average rating, 146 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
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.
Apartment in Leeward Settlement
5 out of 5 average rating, 119 reviews

Luxury Spacious 1 Bed Condo close to the Beach

This 925 sqft luxury 1 bedroom, recently renovated condo provides all necessary amenities for your home away from home. 3 minutes drive 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. We recommend renting a car.

Top Guest favourite
Guesthouse in Leeward Settlement
4.98 out of 5 average rating, 130 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.

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
4.97 out of 5 average rating, 29 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 in your 6-seater Golf Cart or pedal along with the (2) provided pedal bikes. Or relax out by the pool in your private back yard! Book your villa now for an unforgettable experience in paradise!

Top 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, 269 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 • Highest Rated Spa on Island onsite • 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 • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Guest favourite
Cottage in Leeward Settlement
4.9 out of 5 average rating, 147 reviews

Sandpiper Cottage, minutes from the beach

Kick back and relax in this delightful modern one bedroom cottage in the high end residential gated community of Leeward. Grace Bay Beach, most recently voted “The best in the world” is only a 4 minute walk away! This cozy cottage is perfect for a couple, wanting to relax and have some downtime. Complete with full kitchen, washer/dryer/ BBQ, high speed internet with cable TV and all amenities needed for the perfect getaway.

Guest favourite
The villa's exterior is highlighted by a contemporary design, featuring large glass windows and doors. The private pool is surrounded by lounge chairs, with a backdrop of lush greenery and a clear sky. The setting offers a sense of elegance and tranquility.
Villa in Long Bay Hills
4.87 out of 5 average rating, 141 reviews

Gated Long Bay Villa Near Grace Bay with Pool

Gated two-story villa in Long Bay Hills with Caribbean sea views, private pool, and BBQ. Optional private chef, in-house massage, and yacht experiences are available through the host. Long Bay Beach is a 5-minute drive; Grace Bay Beach is 10 minutes away. Complimentary airport transfers for stays of 5+ nights. Designed for groups and families seeking a fully exclusive property with concierge-level service in Turks and Caicos.

Guest favourite
An inviting outdoor space features a modern swimming pool surrounded by tropical landscaping. Lounge chairs provide a comfortable spot for relaxation. Large glass doors open to the villa, enhancing the connection between indoor and outdoor areas. Shade is offered by a large umbrella.
Villa in Leeward Settlement
5 out of 5 average rating, 17 reviews

Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ

Our Lotus Villa is an Oasis in the heart of the Caribbean and escape to a tropical haven in our stunning 3-bed room, perfectly nestled in the heart of Turks and Caicos. This Luxurious retreat promises an unforgettable Island experience, with its pool and garden views, and lavish amenities. The villa is newly built and thoughtfully designed to make your visit unique, comfortable and unforgettable!

Popular amenities for Leeward holiday rentals

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Leeward Settlement?

    Experience the best of Leeward Settlement with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Leeward Settlement?

    Yes! Work meets play with ease at over 120 vacation rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Leeward Settlement vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 280 vacation homes with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Leeward Settlement?

    Leeward Settlement has more than 240 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Leeward Settlement?

    Four-legged friends are welcome in Leeward Settlement. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Leeward Settlement have air conditioning?

    Absolutely! We offer over 40 apartment rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 140 villa rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Leeward Settlement have a bbq area?

    Absolutely! We offer over 100 house rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Leeward Settlement have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Leeward Settlement?

    Enhance your stay in our House Rentals with the most popular amenities: over 100 homes with a bbq area, over 90 homes with air conditioning, over 90 homes with wifi, over 20 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.