
Vacation rentals in Leeward
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Top-rated vacation rentals in Leeward
Guests agree: these stays are highly rated for location, cleanliness, and more.

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🌴

Grace Bay villa | Pool | 3min walk to Beach & Reef
A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

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.

Tropical Guest House
This stylish studio sits within a lush tropical garden behind a semi-detached villa. Enjoy cold AC, a well-equipped space, and your own private grill. Grace Bay Beach is just a 15-minute walk—or less than a minute by car—making it easy to enjoy one of the world’s most beautiful shorelines. Coco Bistro, a renowned island restaurant, and Coco Van are close by, with shops and a grocery store also within easy reach. A fantastic location, great value, and close to everything! 🏠🌴

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.

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!!

"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.

Luxury Private Villa Near GB Beach Pool & Garden
Villa Cocuyo offers complete privacy, comfort, and consistent 5-star hospitality. Couples love the safe and secure , peaceful setting, private solar heated pool, modern interior, and garden oasis. Enjoy fast WIFI, premium amenities, and a spotless space designed for true relaxation. Our 5-star reviews reflect our dedication to exceptional hosting, attention to detail, and a worry-free, private island getaway close to everything including beach

★★★★★ 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

Cheers 🥂 Villa 🌴
Beautiful private Villa in a superb location. Just 2 minutes by car, or 10 minute walk to Grace Bay Beach & Shopping! Cheers Villa is filled with love ❤️ where you can relax in peace during your holiday. We have all the essentials to enjoy the climate of Turks & Caicos. You can relax by the private pool after a day at the beach! 2 bedrooms (King & Queen) 2.5 bathroom. Each room has its own AC as well as the downstairs living space.

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.

Pelican Cottage -Mins. to the Beach!! Car 4 Rent!
Nestled in the tranquil gated community of Leeward, on the heels of the Grace Bay area and the Grace Bay Beach, most recently ranked as the “The Best Beach in the World!”. The upscale Leeward community is within a 5-8 minute drive to the Grace Bay shopping and restaurant district, with about two dozen businesses, including a large grocery store, banks, liquor store, café, phone company, and bookstore.
Popular amenities for Leeward Settlement vacation rentals
Other great vacation rentals in Leeward

1 BR Starfish Stay in the Heart of Grace Bay

Lil Chill -A cozy 1-Bedroom Unit near the beach

1BR Beach Suite w Pool Jacuzzi Kiteboarding K3

Hopewell Villa East/Pool & walk to Gracebay Beach

Cottonflower Villa | Private Beach Chairs GraceBay

NEW *2 BR Villa Maya- BBQ- Golf- Pool in Grace Bay

“Sail Loft Port”, Duplex with a Pool, Beach Access

Sea Villa - Cozy Family Villa Steps From the Beach
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 vacation rentals in Leeward

Total vacation rentals
Explore 310 vacation rentals in Leeward

Nightly prices starting at
Leeward vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 6,530 verified reviews to help you choose

Family-friendly vacation rentals
230 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
260 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wi-Fi availability
310 of Leeward vacation 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!
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