
Holiday rentals in Leeward
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Top-rated holiday 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.

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.

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.

"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.

Modern Villa with Pool Minutes to Grace Bay Beach
Villa Cocuyo offers complete privacy, comfort, and consistent 5⭐️ 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

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!
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.

#10 The Enclave
Conveniently situated within the Royal Turks & Caicos Golf Course, voted the #1 best Caribbean golf course, our location offers easy access to the heart of Grace Bay. Just a short walk away, you’ll find prestigious hotels, world-class restaurants, and shopping. We're also close to Graceway Gourmet supermarket, with the stunning Grace Bay Beach just across the road!

Crescent 6 - 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 place because of the neighbourhoods and quiet area. Place is good for couples, solo adventurers, families and business travellers.

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
Other great holiday rentals in Leeward

SunSeaSand 1Bdrm Seaside Unit B- Long Bay Hills

Aqua Del Rose 1 Bedroom Beach Cottage

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

Blue Tang Villa (2 Bedroom)

Guest Apartment near Grace Bay Beach

Leeward Condo - Sleeps 4

PERIWINKLE | Charming Island Home|Near to Beach

Palms Hideaway II....7 mins to Grace Bay 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 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!
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