
Holiday rentals with a kayak in Leeward Settlement
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Top-rated Accommodation with a Kayak in Leeward Settlement
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Holiday House Rentals with a Kayak

Brighter Days Villa
My mom and I booked extremely last minute and were welcomed right away. The instructions were very clear and the house was easy to find. Beds were very comfortable and we had everything we needed. The only downside was that we could not get the stove/ oven to turn on and weren’t able to cook the food we bought.

Casa de Isle, Taylor Bay, Chalk Sound area
Debbie and Dan were exceptional hosts! They clearly care about their villa and maintain it very well. The villa was stocked with a full usable kitchen with all the tools one would need to cook in. The beds were comfortable, the house was very clean and can’t beat the location just a short walk to the beach. We enjoyed the quick walk to Taylor Bay and the villa was equipped with lots of extras like pool/beach toys, towels, etc, and even had a washer and dryer! Debbie and Dan are a wealth of knowledge and had lots of useful recommendations. Thank you for a wonderful stay at Casa De Isle, we will return!

Tropical Retreat: 360° Views, Pool, Beaches Nearby
Patrice was very quickly responsive to every inquiry and request. The location was beautiful.

Luxury 4 BR Ocean View Villa
We recently had the absolute pleasure of staying at this stunning villa in Turks and Caicos, and it completely exceeded our expectations in every way. From the moment we arrived, we were blown away by the breathtaking ocean views, immaculate design, and thoughtful touches throughout the property. The villa itself is pure luxury. What truly made the experience exceptional was the level of service. The host was incredibly welcoming, responsive, and made sure every detail was taken care of from personalized recommendations to seamless check-in. We will definitely be back again

Turtle Cove - North TCI - Bonefish
It was just absolutely the most perfect trip for our family. We like quiet, want to experience local culture, a little adventure but want to feel safe, etc. From the moment we booked, John was a wealth of information, helpful, accommodating, available, etc. We flew into Provo and stayed 1 night there. He gave us suggestions, got us in touch with a driver who was so accommodating (even with multiple travel plan changes), suggested grocery/liquor options. We ferried to North, picked up our rental car & headed to the house. The house is very spacious, bathrooms for each bedroom, beautiful view, well stocked kitchen, laundry, kayaks available, etc. My husband fly fished the flats out front each morning. We visited a different, amazing beach daily - not a soul on any of them. Spent a day with Captain D fishing - made many memories. Ate out a few times, cooked the rest. Truly - an amazing vacation. Love the area and would love to come back to John's place & visit North Caicos!

Blue Chill Your Tropical Escape in Chalk Sound
This house is perfect; truly a home away from home. It is situated right on Chalk Sound with kayaks and paddle boards for guest use. It is near Taylor Bay & Sapodilla beaches which we frequented and close to Las Brisas restaurant. The house was new, clean, well-maintained and had everything one would need for a comfortable stay. There was plenty of room to relax outside by the pool, as well as beach chairs, beach towels coolers for guest use. All the appliances were clean and functioning well; plenty of towels, kitchen gadgets, plates/silverware for up to 8 people . The hosts, Daphny and Nat were amazing; responsive, attentive and kind! They were great to work with and we are grateful for their kindness. Don’t hesitate to book this home!

Coastal Vibes Villa Near Sapodilla Beach
The house was exactly as described and super clean when we arrived! Good amenities.

Aventine Villa
Perfect spot for our two families (4 adults, 4 kids). The views were absolutely stunning. Short drive to food Las Brisas and Chalkies. Away from the crowded Grace Bay Area but still a short drive there. We kayaked out to the little islands and snorkeled around them. Some highlights: sunrises on the deck, sunsets at Taylor Bay, diving with Dive Provo, 7:00am turtle snorkeling (3 turtles!) at smiths reef, private chef that came to the villa (we had at least two additional meals of leftovers!), sting rays at Sapodilla, potcake place puppy walking, hiking and conch shell hunting at Bird Rock, and of course all the pool, kayak, and pavilion time! This was our second time at a property managed by Island Escapes and with our contact person Julian. He was very friendly and informative. Chalk sound is the best area to stay imo, you definitely need a car but driving/navigating is very easy. Can’t wait to come back!
Cottages with a kayak

Swan cottages #6 Waterfront
What an awesome location! This was our third trip to Turks and Caicos and our third airbnb. This was by far the best location and perfect unit. We are huge fans of Chalk Sound location and this was within very short walking distance of Sapodilla Beach one of the best on the island. The rental was great. Very nice patio, pool, and amenities. Walking distance to Las Brisas restaurant and a short drive to the Little Havana restaurant. The hosts were great. Quick to respond at all times. Never had any issues. Highly recommend.

Your waterfront Dream Getaway Starts Here
Perfect Airbnb find! The location was unbeatable – mere steps from two gorgeous beaches and a grocery store, making our stay incredibly convenient. The house was just as described: clean, comfortable, and on a wonderfully peaceful street. I thoroughly enjoyed my time here and would absolutely recommend it to anyone!

Caicos Cottage, 2 bdrm/2 bath beachfront w/pool
Caicos cottage was everything we hoped it would be - right on the water with the most beautiful views of the ocean and in a quiet little neighborhood. No need for the air conditioning because there were so many windows to let in the cool ocean breeze. We had everything we needed. Mac, the taxi driver/property manager was knowledgeable, helpful, and on top on things. We would definitely stay here again!

SunSeaSand 2Bdrm Seaside Cottage - Long Bay Hills
Close to a Long Bay, easily walk kite gear from the house to a lanch spot. Quiet location with a nice pool big enough for laps. AC worked great. Maintenance was basically onsight right away for any issues and even cut open some fresh coconut for us.

Swan Cottages
We had a great five days here. We rented both cottages and they were perfect for our family of 4. Air conditioning worked perfectly, the pool was nice, plenty of outdoor seating, the kayaks were fun, the location was quiet. It is about 20 minutes from Grace Bay area, but you can't access Grace Bay unless you are stying along the water. We did go to dinner overnight in that area and we did not think it was an issue. There is a beach less than a 5 minute walk away with chairs and umbrellas to rent, but we preferred another more quiet, beautiful beach with shallow water about a 2 minute drive away. A car is needed. Coolers are in each unit, chairs and beach towels provided. the laundry was very helpful. We enjoyed our stay very much! Would highly recommend.
Quick stats about holiday rentals with a kayak in Leeward Settlement
Total rentals
40 properties
Nightly prices starting at
$531 NZD before taxes and fees
Total number of reviews
460 reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Holiday rentals
- Long Bay Hills Holiday rentals
- North Caicos Holiday rentals
- The Bight Settlement Holiday rentals
- Chalk Sound Holiday rentals
- Turtle Cove Holiday rentals
- Sapodilla Bay Holiday rentals
- Cooper Jack Bay Settlement Holiday rentals
- Venetian Road Settlement Holiday rentals
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Rentals with a patio Leeward Settlement
- Kid-friendly rentals Leeward Settlement
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- Rentals with pools Leeward Settlement
- Luxury rentals Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a kayak Providenciales
- Rentals with a kayak Caicos Islands
- Rentals with a kayak Turks and Caicos Islands
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