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Vacation 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.

Guest favourite
Villa in Long Bay Hills
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
11 – 18 Sept
Guest favourite
Guesthouse in Long bay
Villa Kendara~3/30-4/6 OPEN~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
13 – 20 July
Villa in Providenciales
Gardenia Villa
Gardenia Villa. This contemporary Oasis is perfect for a small family or couples, located steps away from the world’s #1 Grace Bay Beach. The villa entrance opens to a bright entryway leading to the living room area with a spectacular view through a wall of sliding doors to the covered deck and pool. The open plan is perfect for entertaining with the dining and kitchen area all part of the living space. The upstairs is flanked by 2 queen sized bedrooms and ensuite bathrooms.
24 June – 1 July

Popular amenities for Leeward Settlement holiday rentals

Stay near Leeward Settlement's top sights

Caicos Conch Farm12 locals recommend
Provo Golf Club14 locals recommend
Blue Haven Resort7 locals recommend
Pelican Beach7 locals recommend
Big Blue Collective17 locals recommend
Caicos Catalyst3 locals recommend

Other great holiday rentals in Leeward Settlement

Guest favourite
Apartment in Caicos Islands
Guest Apartment near Grace Bay Beach
22 – 29 Oct
Guest favourite
Home in Leeward Settlement
Cocodemer, a short walk to secluded Pelican Beach.
28 May – 4 June
Guest favourite
Condo in Leeward Settlement
New! Luxury 1Bed Large Condo
7 – 14 May
Guest favourite
Home in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 – 10 Dec
Guest favourite
Villa in Long Bay Hills
Ocean Dream Studio Blue
24 Sept – 1 Oct
Guest favourite
Condo in Leeward Settlement
Grace’s Condo In Leeward Settlement
18 – 25 Aug
Guest favourite
Villa in Grace Bay
Coco Garden Villa West
14 – 21 June
Guest favourite
Villa in Leeward Settlement
Perroquet | Family Villa near Leeward Beach
14 – 21 Dec
Guest favourite
Home in Providenciales
Sunny Paradise Long Bay
25 Jan – 1 Feb
Guest favourite
Condo in The Bight Settlement
Coral Condo on Grace Bay Beach
15 – 22 Oct
Guest favourite
Apartment in Leeward Settlement
Beautiful Loft newly renovated
11 – 18 Oct
Guest favourite
Home in Leeward Settlement
PERIWINKLE | Charming Island Home|Near to Beach
22 – 29 Dec

Quick stats about holiday rentals in Leeward Settlement

Total rentals

310 properties

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

$30 AUD before taxes and fees

Destinations to explore