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.

Guest favourite

Villa in Long Bay Hills

4.97 out of 5 average rating, 79 reviews

VILLA 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

€ 553 per night
Guest favourite

Guest house in Long bay

4.96 out of 5 average rating, 68 reviews

Villa 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

€ 357 per night
Guest favourite

Home in Leeward Settlement

5.0 out of 5 average rating, 24 reviews

Piccolo 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

€ 1,100 per night

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
Blue Haven Marina5 locals recommend
Pelican Beach7 locals recommend
Big Blue Collective17 locals recommend

Other great holiday rentals in Leeward Settlement

Guest favourite

Villa in Leeward Settlement

5.0 out of 5 average rating, 29 reviews

Perroquet | Family Villa near Leeward Beach

23–30 Oct

€ 622 per night
Guest favourite

Villa in Providenciales

5.0 out of 5 average rating, 14 reviews

Salt Life Villa

9–16 Aug

€ 936 per night
Guest favourite

Villa in Caicos Islands

5.0 out of 5 average rating, 44 reviews

NEW Luxe Private Pool Villa, Golf Course View, BBQ

16–23 Mar

€ 713 per night
Guest favourite

Cottage in Leeward Settlement

4.96 out of 5 average rating, 68 reviews

Sandpiper Cottage, minutes from the beach

12–19 Jan

€ 418 per night
Guest favourite

Apartment in Leeward Settlement

5.0 out of 5 average rating, 17 reviews

Grace’s Condo In Leeward Settlement

1–8 Jun

€ 304 per night
Guest favourite

Home in Leeward Settlement

5.0 out of 5 average rating, 48 reviews

Cocodemer, a short walk to secluded Pelican Beach.

16–23 Aug

€ 372 per night
Guest favourite

Guest suite in Leeward Settlement

4.96 out of 5 average rating, 68 reviews

Erisa Studio near Grace Bay Beach

11–18 Sep

€ 147 per night
Guest favourite

Home in Providenciales

4.96 out of 5 average rating, 79 reviews

Sunny Paradise Long Bay

23–30 Sep

€ 402 per night
Guest favourite

Guest suite in Leeward Settlement

5.0 out of 5 average rating, 22 reviews

The Sandbox

27 Aug – 3 Sep

€ 162 per night
Guest favourite

Villa in Leeward Settlement

5.0 out of 5 average rating, 22 reviews

Caribbean Luxury Waterfront Villa w Housekeeping

18–25 Aug

€ 902 per night
Guest favourite

Flat in Providenciales

4.89 out of 5 average rating, 19 reviews

Cozy Room# 2A is in Venetian Road 7min airport

5–12 Aug

€ 101 per night
Superhost

Villa in Caicos Islands

4.94 out of 5 average rating, 84 reviews

Cheers 🥂 Villa 🌴

16–23 Sep

€ 609 per night

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

€ 19 before taxes and fees

Destinations to explore