What are the top rated Cottage Rentals in Leeward Settlement?

There are a lot of options in Leeward Settlement. If you plan on staying in the Leeward Settlement area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Leeward Settlement: <a href="/property/villa-kendara-bk-5-2-on-private-gated-beachfront-guesthouse-panoramic-view/HA-121942102" class="class="static-page-link"">Villa Kendara~BK 5/2 ON~Private~Gated~BeachFront GuestHouse~Panoramic View</a> <a href="/property/byculla-4-br-villa-canal-front/HA-3212541963" class="class="static-page-link"">Byculla 4 BR Villa - Canal Front</a> <a href="/property/popular-ocean-front-villa-with-great-service-and-great-value/HA-3211191012" class="class="static-page-link"">Popular ocean front villa with great service and great value</a> <a href="/property/villa-vivace-new-luxurious-seaside-home/HA-321305299" class="class="static-page-link"">Villa Vivace - New Luxurious Seaside Home</a> <a href="/property/sunsetone-beach-villa-golf-cart-6-seats-kayaks-sups-free-beach-set-up/HA-321815169" class="class="static-page-link"">SunsetOne Beach Villa - Golf Cart 6 seats, Kayaks, SUPs; Free Beach Set Up</a> <a href="/property/kick-back-and-relax-tiki-style/HA-321377589" class="class="static-page-link"">Kick Back and Relax Tiki Style!</a> <a href="/property/private-resort-style-villa-and-pool-close-to-beaches/HA-3211654277" class="class="static-page-link"">Private Resort Style Villa and Pool close to beaches</a> <a href="/property/barefoot-bliss-leeward-villa-with-private-pool-short-walk-to-the-beach/HA-3212321098" class="class="static-page-link"">Barefoot Bliss - Leeward villa with private pool &amp; short walk to the beach</a> <a href="/property/cozy-chic-grace-bay-beach-pets-welcome/HA-3211830581" class="class="static-page-link"">Cozy &amp; Chic Grace Bay Beach Pets Welcome!</a> <a href="/property/waterfront-private-pool-hawksbill-house-in-safe-prestigious-area/HA-3211787413" class="class="static-page-link"">WATERFRONT&amp; Private POOL @Hawksbill House in safe, prestigious area</a>

How much does it cost to rent a cottage in Leeward Settlement?

The average cost for a cottage rental in Leeward Settlement is $436 per night. Thewisebeach has a wide list of great cottages near Leeward Settlement that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Leeward Settlement that allow pets?

Yes, here are the top cottage rentals in Leeward Settlement that allow you to bring your pet: Silver Palms # 2 – Exclusive Long Bay Beachfront Retreat with Pool Charming Cottage Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay Palmwell Cottage Villa Tropica - Near Grace Bay Beach - Newly Remodelled Villa Seabatical Blue Haven Resort - All-Inclusive Private Oasis with Pool <a href="/all/turks-and-caicos/providenciales/leeward-settlement" class="class="static-page-link"">See all pet-friendly vacation rentals in Leeward Settlement on Thewisebeach</a>

Do you have any rental cottages in Leeward Settlement that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Leeward Settlement to find one that works for you.

Are there quality cottages in Leeward Settlement that have indoor swimming pools?

As of 2026, the data from Thewisebeach shows that there are Over 10 private swimming pools or cottages with indoor pools in the Leeward Settlement area along with other great amenities.

Leeward Settlement Cottage Rentals By Owner

Silver Palms # 2 – Exclusive Long Bay Beachfront Retreat with Pool

From US $874

9.8 (174 Reviews)

Cottage

Silver Palms # 2 – Exclusive Long Bay Beachfront Retreat with Pool

Air Conditioner
Parking
Pool

Leeward Settlement Cottage Rentals & Holiday Homes

Find the best cottages in Leeward Settlement - We found 10 exact matches

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