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Holiday rentals in Leeward

Find and book unique accommodation on Airbnb

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
4.97 out of 5 average rating, 58 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
Home in Leeward Settlement
5 out of 5 average rating, 34 reviews

Upper East Side Estates Gated Community Leeward

Escape to paradise at Waves of Blue 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 (4) provided pedal bikes. Relax indoors with the brilliant large screened TVs equipped with all the latest streaming services. Book your villa now for an unforgettable experience in paradise!

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, 101 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 modern kitchen area features a central island with seating for four. Stainless steel appliances complement white cabinetry and light countertops. A cozy living space is arranged with a gray sofa and a coffee table, providing a welcoming environment. Steps lead to the upper level.
Flat in Leeward Settlement
4.93 out of 5 average rating, 41 reviews

Beautiful Loft newly renovated

Experience the vacation of a lifetime in our stunning loft in Providenciales, Turks and Caicos. Boasting a proximity location where all celebrities stay in Leeward, this newly renovated modern apartment features sleek design, a fully equipped kitchen, and a large private balcony. Immerse yourself in tranquility, steps away from pristine beaches and exquisite dining. Ideal for a romantic escape or a peaceful island adventure! The best restaurants on island are a 5 minute drive away!

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.
Apartment in The Bight Settlement
4.95 out of 5 average rating, 119 reviews

Oasis | 1 BR Condo | Vista Azul | 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
An outdoor area features a swimming pool bordered by sun loungers and a shaded seating area. Umbrellas provide shade, while lush greenery and ocean views create a serene environment. The clear water of the pool reflects the blue sky, enhancing the inviting space.
Villa in Providenciales
4.99 out of 5 average rating, 115 reviews

Villa DelEvan 4B / 1-bedroom 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.

Top guest favourite
Guest house in Leeward Settlement
4.97 out of 5 average rating, 118 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 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.
Apartment in Providenciales
4.92 out of 5 average rating, 256 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

Superhost
Cottage in Leeward Settlement
4.91 out of 5 average rating, 128 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.

Superhost
A modern living area is shown, featuring a gray couch with green decorative pillows. A light-colored coffee table is positioned in front of the couch. Two framed pieces of wall art enhance the space. A chair is also visible, contributing to the open layout.
Flat in Grace Bay
4.8 out of 5 average rating, 184 reviews

Crescent 4 - Grace Bay beach 2 min walk

My place is just a two minute walk to one of the most beautiful beaches in the world, Grace Bay beach. Absolutely great spot to walk to many restaurants, bars, casino, grocery store and shopping centre at Salt Mills. You’ll love my studio because of the neighbourhoods and quiet area. Studio apartment has open concept, only door for the bathroom. Place is good for couples, solo adventurers and business travellers.

Superhost
An inviting interior space combines a comfortable green sofa with a vibrant orange wall. A queen bed is visible in the background, surrounded by natural light from glass doors. Decorative pillows add color, while a ceiling fan and art piece enhance the cozy atmosphere.
Guest house in Leeward Settlement
4.91 out of 5 average rating, 151 reviews

Pelican Cottage -Mins. to the Beach!

Nestled in the tranquil, gated community of Leeward, just minutes from the Grace Bay area and Grace Bay Beach, frequently ranked “The Best Beach in the World”. This exclusive enclave offers both privacy and convenience. Leeward is only a 5–8 minute drive from the Grace Bay shopping and restaurant district, which includes a large grocery store and many other amenities.

Guest favourite
A tranquil pool area is surrounded by lush tropical foliage, with palm trees and flowering plants presenting a vibrant backdrop. A pair of yellow lounge chairs is positioned near the water's edge, inviting relaxation under a bright blue sky dotted with clouds.
Flat in Leeward Settlement
4.95 out of 5 average rating, 281 reviews

Leisure in Paradise - steps from Beach, with pool

Wake up on a Mocking bird singing in the garden, sun rays sparkling through the lush green while you drink your cup of tea or coffee on your private screened patio. Take a walk in the topical garden and have a refreshing swim in crystal clear pool or take a short walk (3 minute) to the turquoise ocean and white sandy beach.

Popular amenities for Leeward holiday rentals

Frequently Asked Questions

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

    Experience the best of Leeward Settlement with our condo rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Yes! Dive into the perfect getaway at one of over 30 apartment rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

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

    Yes! Work meets play with ease at over 20 house rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Absolutely! We offer over 60 villa rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

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

    Leeward Settlement has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Leeward Settlement have a gym?

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

  • Do villa rentals in Leeward Settlement have air conditioning?

    Absolutely! We offer over 130 villa rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

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

    Four-legged friends are welcome in Leeward Settlement. Choose from more than 10 house rentals for guests traveling with pets.

  • 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 80 homes with wifi, over 80 homes with air conditioning, over 100 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Leeward

  • Total holiday rentals

    Explore 320 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at £66 per night before taxes and fees

  • Verified guest reviews

    Over 7,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    230 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    270 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    310 of Leeward holiday rentals include wifi 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!