
Leeward Settlement vacation rentals
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Top-rated vacation rentals in Leeward Settlement
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Other great vacation rentals in Leeward Settlement

Beach Landing Villa
Colton and Mallory were gracious hosts. We appreciated the welcome snacks and beverages when we arrived. The beach chairs were super helpful and we loved having the bikes to ride into town for dinner a few nights. While the home is nice, one of the bedroom AC units seemed to have issues the entire time we were there…leaking down the wall and all over the floor. We followed all of the guidelines with not leaving doors or windows open when running it, but I think it needs to be replaced possibly as the other two worked beautifully. And again, nice house and having the pool was a hit with our kids but we paid more than my husband and I think it was likely worth. So much so, I had a hard time enjoying our vacation as I was a bit sick to my stomach we had spent so much for a home on a busy street with construction next door. Again, great hosts but I’m not sure we’d pay that much to stay there again.

Water’s Edge Studio
We had a wonderful stay! Alison’s studio is perfect. Cute little kitchen and bathroom. Comfy bed and amazing views to wake up to. The location is great to explore North Caicos and easy to get to Middle Caicos. We thoroughly enjoyed our few days in this private oasis.

2 Bedroom Spectacular Views
This villa was even better than the photos depicted. Absolutely perfect in every way. Chalk Sound is a truly special place as are the nearby beaches (Sapodilla Bay, and a particular favorite was the very unique Taylor Bay Beach). A rental car for this location is a must, and the short trip to Grace Bay is very worth it (both the town and the beach). You can bring the beach chairs Terri provides or easily rent chairs and umbrellas there. Felt like a luxury hideaway, but with easy access to all of the hot spots around the island. Would give 6 stars if we could!

Sea Villa - Cozy Family Villa Steps From the Beach
beautiful property, close to beaches/restaurants, responsive host!

1 BR Apt w/pool - Long Bay Hills #2
Do yourself a favor & book this place!! Spotless home with perfect AC units (I'm usually VERY picky with cleanliness), very WFH friendly (desk, chair, very good wifi, etc), and very safe location! I stayed here as a solo female traveler & never felt the need to even lock my door! Perfect place to stay long term, too - comes with everything you need, it's away from all of the resorts/noise (& fratty people). Incredible price, too! I will only come back to TCI if this home is available! I stargazed in the pool every single night. Jim & Maria are incredible hosts who were so helpful in every way. For example, I'm pretty sure Maria took the batteries out of her fire alarm to put into mine, so she suffered all night, but I didn't have to. They also lent me their paddleboard, gave me endless tips/tricks, & were so kind! Really made the island feel special. Thank you SO much for everything!

Cocodemer, a short walk to secluded Pelican Beach.
COCODEMER, THE PLACE YOU WANT TO BE! WE FELT WE WERE LIVING IN A TROPICAL VILLA AS YOU SEE IN MOVIES! David and Amanda’s home is truly fantastic- a hidden gem. We greatly enjoyed our stay! – Steady cross breeze , vaulted ceilings! Furnishings & Decorations are VERY impressive ! Huge screened in covered porch overlooking a beautiful pool. Comfy seating on the porch & a large dining table for outdoor meals, we greatly enjoyed. The kitchen is well stocked – it had everything we needed and more. Bedrooms are excellent – each with their own bathroom. Very comfortable beds. The pool is beautiful, surrounded with Palms Trees , concrete deck & chairs for lounging . Marvelous property within a short walk to the amazing Grace Bay and Leeward beaches. An oasis in the middle of paradise! Quiet location! David and Amanda are the quintessential hosts! David is always reachable with an excellent response time! We will be back for several years to come! thank you David & Amanda !

Island Hideaway for Two
I found getting to the place completely easier by taking the road all the way up using the third entrance to the beach side . After you. Pass the big beach chair , pass the second road to the beach and take the third , it’ll literally take to the place it’ll be on your left

Grace’s Condo In Leeward Settlement
This place was incredible. Walkable to the beach, having the bikes was so helpful, and the fact that the host provided sunscreen, aloe, and bug spray was so helpful. I had to reach out to the host a few times and she was very responsive and helpful. I would 100% recommend this place to anyone.
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 villa rentals with a dedicated workspace in Leeward Settlement?
Yes! Work meets play with ease at over 50 villa rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Leeward Settlement have a bbq area?
Absolutely! We offer over 110 house 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 house rentals in Leeward Settlement have wifi?
Absolutely! We offer over 90 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 30 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 140 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 Villa Rentals in Leeward Settlement?
Enhance your stay in our Villa Rentals with the most popular amenities: over 30 homes with a gym, over 140 homes with air conditioning, over 140 homes with wifi, over 70 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Grace Bay Vacation rentals
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