
Villa holiday rentals in Leeward Settlement
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Top-rated villa rentals in Leeward Settlement
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Popular amenities for villa rentals in Leeward Settlement
Private villa rentals

Sea Sun Relax - villa 5 min walk to Grace Bay
Great home on the island. We loved having the space and comforts to come back to after busy days of excursions. The pool, outdoor space and beach chairs were highlights. Would absolutely stay here again if we ever come back to Provo.

‘My Little Hideaway’ at Lucayan Cays
We really loved our two week stay here. The rental unit was impeccably clean and well equipped. The beautiful bright bedroom had plenty of closet space and a comfortable king sized bed. The bathroom was very nice too - a great shower with lots of hot water. Any questions we had were promptly dealt with by the friendly hosts.They even brought us a surprise Valentine's Day gift of wine and chocolate, demonstrating their attentiveness and kindness. Our favourite spot was up on the deck by the private pool, overlooking the spectacular coloured waters of Chalk Sound. There are also two quiet beaches fairly close by to walk and see the sunset. We were looking for a quiet and peaceful spot to unwind and celebrate our anniversary - we could not have chosen a better place. We would love to return here and highly recommend Tiajuana's property.

Modern two-bedroom Villa with pool!
Beautiful house! Met the needs of our party of 4. Hosts were great communicators and provided useful recommendations. Transportation is expensive. Essentially a $100 roundtrip most places. A few excursion hosts provide roundtrip transportation. They are pretty accommodating. I recommend having the airbnb location pinpointed on google maps when traveling from airport to airbnb. They did not know where villa was located so the gps was necessary. Most likely will be first stop as grace bay is located further out. Nonetheless, had an amazing stay!

WOW! Waterfront Chalk Sound Oasis w/ Infinity Pool
I can’t speak highly enough our stay at this villa. The pictures really don’t do it justice and I would’ve stayed longer if I could! The backyard is absolutely breathtaking and I would say that this was probably my favorite stay/trip of all time. Thank you so much.

Peaceful island getaway in Long Bay (New 2BR)
Everything about the property was described just like the picture..Host was amazing and we will for sure be staying again..Very peaceful location…I loved it!

Nirvana's Nest
I booked this for some colleagues that were going to Turks very last minute for a work trip and Jasmine was great! She was very quick and thorough to communicate and made it very easy.

Rockspray Villa | On Point in Ocean | Waterfront |
Rockspray villa is just as beautiful and just as remote as the pictures and descriptions represent. We had a phenomenal time and heavily used the amenities (paddleboards/kayaks). If there's any feedback I wish I would have read, it would have been on the wind this side of the island receives and the current the beautiful water carries. It made swimming/snorkeling outside of the shallow bay area pretty hard (but amazing to view). Out of the host's control, there was also safety issues on this side of the island caused by the unlucky timing of an illegal immigration boat coming ashore. Despite all the police and border presence, I don't think we expected such heavy security measures required to enjoy the vacation (including alarming the villa during away and home situations). As first time visitors traveling without friends, we would have stayed in the Grace Bay resort area instead to get a bit more community. However, I would absolutely stay here again if the price/value was right.

The Haven
We had an absolutely great stay at this Airbnb in Turks and Caicos! The property was clean, spacious, and the host was incredibly welcoming and quick to respond to any questions, making check-in and everything else very easy. The place had everything we needed to feel comfortable —comfy beds, a well-equipped kitchen, and even some beach gear to use. I’d highly recommend this place to anyone visiting the islands!
Luxury villa rentals

Grace Bay/ Luxurious Coconat Villa 3 Bed + Pool
Our family of 5 (three teens) had an amazing stay at Nathalie’s place. First of all, the location is perfect… a short drive, or walk, to the Cocovan for tacos, or to the Main Street for coffee and shopping. The house was very clean and comfortable and all of our needs were met and then some. There’s some construction in the surrounding area and on the island as a whole (at the time of this writing) as it’s a desirable location for vacation homes and residences, but the area around Nathalie’s house is already developed and was very quiet… an idyllic, peaceful retreat. Nathalie was extremely responsive and went above and beyond to provide great recommendations for restaurants and beach spots. Our favorite day was our boat excursion with Captain Andy (recommended by Nathalie). We were able to get a tour of the island from the ocean and he took us to some remote, practically untouched beaches to explore. Breathtaking, stunning beaches. We would undoubtedly stay here again!!

Villa Blu - A contemporary 3 BDR/BTH Villa minutes
Our stay at Villa Blu was perfection! Our trip was 5 girls for a birthday celebration and the accommodations were on point! The walk to the beach along with the beach accessories was a HUGE highlight. George our concierge was lovely, fast to answer texts and offered local recommendations. We also appreciate told the suggested taxi driver, made us feel safe knowing this person was recommended and he was there whenever we asked. The kitchen was fully stocked, we were able to have breakfast everyday at the villa and a few grilled dinners. If I ever get to return to Provo I would 100% stay here.

Luxury Modern villa with pool
Perfect villa!!! Was very clean and looked exactly like the pictures!! Loved the privacy of the villa will definitely stay here every time I come to the island!! Perfect way to spend a birthday trip!!

Hang Five Surf Villa in Long Bay
My family and I really enjoyed our time at Katie's place. The location was private but still close to great beaches and restaurants. The place itself was clean and organized with great amenities. Katie provided great instructions/recommendations and she was very responsive. The only downside was the ongoing construction around the property. Overall 10/10 would definitely recommend this place to anyone coming to beautiful Turks and Caicos!

Blanca: Taylor Bay Beach-Ocean View
This villa is nestled in paradise. We loved it so much! The views are breathtaking. The couple minute walk to Taylor Bay was the convenience we were looking for. Watching the sunsets from the balcony was the perfect end to the day. Our favorite meals came from nearby restaurants so we only went to Grace Bay a few times. Perfect vacation.

Luxury 3B Ocean View Villa/Pvt Pool, Walk to Beach
We had a wonderful stay at Blue lotus villa! The location is great where Grace Bay is 10 min away, there’s a walkable beach near the house. The house itself is very nice and neat - the pictures are accurate. On top of that, Raymond and his property manager were very responsive and accommodative. I would stay here again!

Live style villa
We had a very pleasant stay at Geraldine’s. We were a party of 8, including my parents who are 70, and having a one level house without stairs was very helpful. Geraldine and her husband Reinaldo were super responsive to our needs and made the check in process easy. The house looks just like the photos. Super clean and tidy. The espresso machine was a nice surprise and well stocked with coffee beans. The backyard with the pool, seating and play area, is beautiful and was a hit with our teenage kids and 10 year old. The pool is not heated but warm from the sunny temps. There is a golf cart available for guests to use which was helpful getting to the beach area (5 mins away) and the closest marketplace (also just 5 mins away). The downtown area is less than a 10 minute drive by car which takes you to different restaurants and shopping areas. Great house, close to everything, private and in a safe gated community.

100 Steps to Beautiful Grace Bay Beach!
This villa was a perfect getaway for our large group of 11 (9 adults and 2 children). We loved the outdoor dining area, beautiful pool, privacy, and the nearby beach! There was plenty of space for our group to spread out. The walk to the beach took about 3-5 minutes. When we experienced an issue with the plumbing on our first day, the hosts were very responsive and made sure it got repaired the next day. The care they have placed in the property is evident and we enjoyed our stay! We hope to return some day.
Villa rentals with a pool

Unique, Modern Cozy & Private | 2 minutes to Beach
The villa was very comfortable and clean. I appreciated the yoga mat and weights for daily exercise routine. There are Smart TV’s in bedrooms to catch up on your Netflix programs and a regular TV with cable stations in the main room. The pool was wonderful, clean, refreshing. Lots of white, plush bath towels and beach towels in lovely bathroom areas in both bedrooms. We love the Leeward location because it is quiet and off the beaten path yet easy to access downtown and Grace Bay Beach. A rental car is necessary. Pelican Beach is a quick drive away or an easy walk. The beach is absolutely beautiful with awesome sunsets … My husband and I had a wonderful, restful vacation in this well appointed villa. Rochelle was easily reachable to answer questions and responded promptly.

Pelican Beach Villas 2
This Airbnb was incredible. The host was amazing - responsive, friendly and so helpful! One of the guests in our groups had been to North so had a really good idea of what we’d be getting into - but exceeded all expectations! We were the only people on the beach and it was so peaceful and relaxing!! A few helpful tidbits for north newbies - grab groceries on Provo before coming over (we brought cooler bags and bought ice for transport) and got all of our water from the local store and filled up throughout the week, went out on captain D’s boat (excellent)! Try to bring an umbrella (zero shade by the pool) and bug spray when lounging by the pool (which is expected). AC worked great and we were up with the sun (curtains were thin) but that’s was fine by us, we just made sure to go to bed early. Can’t say enough great things about this place! But if you are looking for fancy touristy resort, stay on Provo (please), if you want relaxing paradise - come to North but keep it a secret 🌴

Sapodilla Bay - Walk to the Beach!
Ari’s villa is exactly as described and is on the southern, quieter, and more private side of the island. Rental car is a must for dinner/groceries/shopping, but there is a beach within 5 minutes walking distance and he provided a cooler, umbrella, and beach towels. The rooftop terrace is a great place to catch the views and the sunrise. Thanks so much, Ari!! Highly recommended!!

The White House TCI Guests house
This surpassed my expectations. It was perfect for the entire family including the kids. I will definitely be rebooking in the future.

New Listing! Modern Comfort! Private Pool!
It was our first time in Turks and Caicos. We are a family of four, and my two kids love having their own room. The house is in a fantastic location, very clean, and Wendy and Bianca were wonderful, always eager to help. We definitely look forward to returning.

Canal Front Luxury Villa!
We had the pleasure of staying at this breathtaking Villa nestled right on the water, and it was nothing short of amazing. From the moment we arrived, we were captivated by the serene beauty of the surroundings and the impeccable design of the property. The location was perfect for us as we were seeking tranquility and natural beauty. It sat right on the edge of the canal, offering panoramic views that truly took our breath away. The accommodations themselves were equally impressive. The interior was elegantly furnished with a blend of modern amenities and cozy touches that made us feel right at home. The bedrooms were spacious and comfortable, with large glass doors in the master bed that allowed for stunning views of the water from the comfort of my bed. Lori's hospitality was exceptional. She paid attention to detail and was ensured that all our needs were met. A beautiful home away from home that we can't wait to book again! Thanks for everything Lori, you made our stay memorable!

NEW *2 BR Villa Maya- BBQ- Golf- Pool in Grace Bay
We really enjoyed our 5days stay at Maya Villa. Very modern, clean and well organized with everything you need. Felt very much at home. Location was peaceful, yet close enough to get round to the main part of town. Very responsive host with clear guidance and support. Highly recommend this beautiful home for your vacation!

Ocean Dream Studio Blue
This is a nice, fairly secluded location. Note that nothing is really walkable but you’re a short car trip to Grace Bay. I would say the pool is small (we ended up not really using it) and if the weather is good the ocean is much nicer anyway. The complex provides ice, some drink coolers and some beach chairs (these were on their last legs.) The mgmt co was very helpful and responsive. The kitchen had all the tools to make breakfast and grill a few meals - helpful due to the high costs in TCI. The bathroom was pretty nice and outdoor shower facilities helpful. The couch inside isn’t really comfortable - the space is so small that this is relevant if you’re at home, since there’s no where else to sit inside. All said this is a nice spot if you’re happy with seclusion and don’t want resort life.
Quick stats about villa rentals in Leeward Settlement
Total rentals
140 properties
Nightly prices starting at
£139 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
140 properties are a good fit for families
Rentals with a pool
140 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
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