Holiday rentals in Leeward Settlement
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Top-rated holiday rentals in Leeward Settlement
Guests agree: these stays are highly rated for location, cleanliness and more.
Villa in Long Bay Hills
4.97 out of 5 average rating, 79 reviewsVILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
Take it easy at this dreamy, unique and tranquil getaway. Villa infini brings privacy and relaxation all in one , Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway . Bali like dip pool that can create amazing instagramable moments . Located in long bay , 5 minute walk to long bay beach . 5 minute drive to IGA gourmet and 6 minute drive to grace bay beach KING SIZE BED QUEEN SIZE SOFA BED Famous Tiki bar pick up 2min away
20–27 Oct
Guest house in Long bay
4.96 out of 5 average rating, 68 reviewsVilla Kendara~BK 6/22 & On~Gated~SeaFront GH~View
Private~Gated~Seafront~Unique Loc~Beautiful by Nature~Panoramic Water & Bay Views~A+ Sunrises/Sunsets~5 min to Grace Bay, Stores, Restaurants, Marina~Exclusive ”Johnson Guide to Provo & Car Travel Guide~LOFT FOR KIDS~Fully Equipped~Loaded with Supplies~Pool, CoralStone Deck, Pergola for Shade, BBQ, AC, Fans, TV, DVD, Phone, Wi-Fi, Snorkel Gear, Portable Beach Chairs & Umbrella~Island Partner Discounts for Car Rental, Water Sports/Eco-Tours, Cruise, Massages~Swim, Snorkel, KiteBoard, PaddleBoard
19–26 Oct
Home in Leeward Settlement
5.0 out of 5 average rating, 24 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
*Great for couples and families - Pool - Heated SPA - On the canal - Sups - 5 min to the beach* Piccolo Ponte is an elegant 3 bedroom canal front Caribbean property that sits on an acre of private tropical garden where friends and family gather together to relax and enjoy a laid-back vacation island-style. Located directly on the clear and turquoise canals of the prestigious Leeward Settlement, just a few minutes away from Blue Haven Marina and many beach accesses and watersports operators.
22 Feb – 1 Mar
Holiday rentals for every style
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Popular amenities for Leeward Settlement holiday rentals
Other great holiday rentals in Leeward Settlement
Villa in Leeward Settlement
5.0 out of 5 average rating, 29 reviewsPerroquet | Family Villa near Leeward Beach
23–30 Oct
Villa in Providenciales
5.0 out of 5 average rating, 14 reviewsSalt Life Villa
9–16 Aug
Villa in Caicos Islands
5.0 out of 5 average rating, 44 reviewsNEW Luxe Private Pool Villa, Golf Course View, BBQ
16–23 Mar
Cottage in Leeward Settlement
4.96 out of 5 average rating, 68 reviewsSandpiper Cottage, minutes from the beach
12–19 Jan
Apartment in Leeward Settlement
5.0 out of 5 average rating, 17 reviewsGrace’s Condo In Leeward Settlement
1–8 Jun
Home in Leeward Settlement
5.0 out of 5 average rating, 48 reviewsCocodemer, a short walk to secluded Pelican Beach.
16–23 Aug
Guest suite in Leeward Settlement
4.96 out of 5 average rating, 68 reviewsErisa Studio near Grace Bay Beach
11–18 Sep
Home in Providenciales
4.96 out of 5 average rating, 79 reviewsSunny Paradise Long Bay
23–30 Sep
Guest suite in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsThe Sandbox
27 Aug – 3 Sep
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
18–25 Aug
Flat in Providenciales
4.89 out of 5 average rating, 19 reviewsCozy Room# 2A is in Venetian Road 7min airport
5–12 Aug
Villa in Caicos Islands
4.94 out of 5 average rating, 84 reviewsCheers 🥂 Villa 🌴
16–23 Sep
Quick stats about holiday rentals in Leeward Settlement
Total rentals | 310 properties |
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Rentals with a pool | 260 properties have a pool |
Pet-friendly rentals | 10 properties allow pets |
Family-friendly rentals | 240 properties are a good fit for families |
Total number of reviews | 4.8K reviews |
Nightly prices starting at | € 19 before taxes and fees |
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Holiday rentals
- Taylor Bay Holiday rentals
- North Caicos Holiday rentals
- Long Bay Beach Holiday rentals
- Sapodilla Bay Holiday rentals
- Chalk Sound Holiday rentals
- Turtle Cove Holiday rentals
- Salt Cay Holiday rentals
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