
Leeward Settlement vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Leeward Settlement
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Leeward Settlement vacation rentals
Other great vacation rentals in Leeward Settlement

Villa Cocuyo Micro Villa with pool
This place was exactly what we were looking for. Beautifully situated in a quiet area but close to restaurants and beaches. It was clean and looked just like the pictures. Jeff was very responsive to our questions and his recommendations were spot on. Would absolutely stay again.

BeachHaus Villa with ocean view and private pool
Dallas’ house was gorgeous and had a beautiful view of the ocean on the main floor and in the master bedroom. The kitchen was well appointed. The outdoor kitchen and grill worked out great for us as well on a couple of nights we stayed in. We loved the outdoor shower, too and used it daily as soon as we discovered it. It truly was a 3 minute walk to the beach. The pool at the house was great and provided a lot of late afternoon/evening entertainment when we needed a break from full sun. Dallas provided excellent restaurant and snorkeling recommendations. When we had a short power outage she was incredibly responsive and got an electrician to the house right away. If you’re looking for a relaxing vacation with a beautiful view and plenty of space for a family or a larger group, look no further.

Colibri Gardens Villa - Great value in Grace Bay
We had 2 families at Erin’s place for the week. 4 adults and 4 kids (11-13year olds). The place accommodated everyone super comfortably. The location was incredible! Walking distance to beach, shops, grocery, restaurants etc.. I feel the need to mention that we all felt safe the whole time, even walking at night. We rented a car and explored other beaches around the island with short day trips, but the Grace Bay beach (probably 5-10 min walk) was awesome. The kitchen amenities were perfect as we cooked a lot. Grill was clean and worked great too. The huge outdoor screen porch was a favorite for hanging in the morning and night time too. If you are thinking about Erin’s place, DO IT! Fantastic vacation all around!

Vista Blue Rental-Grace Bay Beach just 4 mins away
Candice's place was just what we would have hoped for. Candice was responsive to our every communication. One of the AC units wasn't operating as it should, and she immediately had an AC repairman there (arranged within minutes). The place was very clean and orderly. The inside of the unit is better than pictured. Though, the outside isn't anything to look at (which may be why there aren't any exterior pictures). It's located right next to Royal Turks and Caicos Golf Club, and very convenient to downtown, beaches, and stores. A great experience. Thanks Candice!

Spectacular view 2 bedroom condo Grandview 205
This place is a dream. The views were spectacular, the beach was RIGHT THERE! The pool was nice and never crowded. The set up on the beach was amazing - so many lounge chairs and beautiful white umbrellas. And you could walk to anywhere in grace bay ON THE BEACH. The walk to the Ritz was no more than 15 min for example. I just can't say enough about this place. Also Matthew was fantastic. gave us great recommendations, always attentive. Will definitely be back !

Oceanfront two bedroom condo with stunning views
Thank you so much, Jasmine! We really enjoyed staying in your place and appreciate the amenities offered at your property! I would recommend prospective guests to the Turks and Caicos to consider residing at Jasmine’s place because the description in the advertisement matches the experience. Thank you, again, Jasmine for such a pleasant, lovely, and unforgettable place to experience the joys and beauty of TCI! We will definitely look you up next time we come back! Thanks!

Sun Villa-Family friendly Villa Close to the Beach
Everything was so close to our Airbnb and it was plenty of room for the whole crew. We were able to ride the golf cart as well. Airbnb was roomy and also had cold water inside for use which was needed as it’s so hot plus the pool which was nice

Pelican 12 Villa Longbay Kiteboarding beach
Excellent stay. Communication was great. Unit was very clean and was as described. Hosts are very friendly and helpful. Will definitely look at this place first next time we go to Turks and Caicos
Quick stats about vacation rentals in Leeward Settlement
Total rentals
330 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
6.4K reviews
Family-friendly rentals
260 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
280 properties have a pool
Frequently Asked Questions
Are there Leeward Settlement condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 condo rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!
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 $190 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there apartment rentals with a dedicated workspace in Leeward Settlement?
Yes! Work meets play with ease at over 10 apartment 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 70 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 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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 villa rentals in Leeward Settlement have a gym?
Absolutely! We offer over 30 villa rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Leeward Settlement have air conditioning?
Absolutely! We offer over 30 apartment 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 10 homes with a gym, over 90 homes with air conditioning, over 90 homes with wifi, over 110 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Grace Bay Vacation rentals
- Grand Turk Vacation rentals
- Long Bay Hills Vacation rentals
- North Caicos Vacation rentals
- Long Bay Beach Vacation rentals
- The Bight Settlement Vacation rentals
- Chalk Sound Vacation rentals
- Turtle Cove Vacation rentals
- Sapodilla Bay Vacation rentals
- Cooper Jack Bay Settlement Vacation rentals
- Santo Domingo Vacation rentals
- Las Terrenas Vacation rentals
- Family-friendly rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Apartment rentals Leeward Settlement
- Pet-friendly rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Villa rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- House rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Rentals with a patio Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a fireplace Leeward Settlement
- Beachfront rentals Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Rentals with pools Leeward Settlement
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom