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Waterfront vacation rentals in Leeward Settlement

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Leeward Settlement

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Villa in Providenciales and West Caicos

4.84 out of 5 average rating, 125 reviews

Secluded 3 BR Villa on Taylor Bay -Place De La Sol

The luxury of privacy is what this villa is all about. A few steps through a private tropical path takes you to the pristine waters and powder sand beach that is Taylor Bay. This Villa is split between the main villa which hosts 2 bedrooms, living room, bathroom and kitchen/dining. The Master Suite is located across the patio with it's private bathroom and outdoor/indoor shower. Sunsets are 2nd to none and should be done at least once beachside since the villa faces west. **12% TCI Tax Included

Rental unit in Long bay

4.95 out of 5 average rating, 78 reviews

Villa Kendara~BK APR 5 ON~Private~SeaFront GH~View

Private~Gated~Seafront~Convenient~Panoramic Water Views~Beautiful by Nature~A+ Sunrises/Sunsets~Swim in Pool or Sea, Snorkel~5 min to Grace Bay Hub & Beaches, Restaurants, Stores, Marina~Exclusive "Johnson Guide to Provo"~Fully Equipped with GMT Kitchen, Amenities, Supplies, AC, Fans, Wi-Fi, TV, DVD, Phone, Safe & LOFT FOR KIDS~CoralStone Deck, Pergola for Shade, BBQ~Snorkel Gear, Portable Beach Chairs & Umbrella~Island Partner Discounts for Car Rental, Water Sports/Eco-Tours, Cruise, Massages

Home in Leeward Settlement

4.96 out of 5 average rating, 25 reviews

GETaWAY home@OCEAN PEARL- leeward near Graceway

Newly built 2 bed 2bath stand alone guest house is located in a Leeward gate. It's closer to all the activities, restaurants, golf, Grace bay, water sports, excursion pickup points, enjoy and relaxation in beautiful island. It's 11 minutes walk away from sunset, pelican beach, marina, pool, barbecue, We provide pre-arrival island support and assist with local reservations for excursions, water sports and restaurants, car rentals, safe to stay in island. Note: we have two houses in premises

Villa in Leeward Settlement

5 out of 5 average rating, 33 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.

Villa in TC

4.88 out of 5 average rating, 106 reviews

Waterfront Point Villa - A Taste of Island Living

This beautiful 3 bedroom, 2.5 bath waterfront villa at the end of a secluded cul-de-sac in a quiet neighborhood is the perfect place to enjoy a taste of island life. With 300-plus feet of waterfront, you can take in the view from wrap-around balconies, kayak, paddle board, and snorkel in the crystal clear canal, or go for a dip in the private pool. The bright, airy rooms have split-air units and ceiling fans to keep them cool and comfortable. Many amenities will make you feel right at home.

Rental unit in Providenciales

4.9 out of 5 average rating, 164 reviews

Beautiful Sunset Villa with Infiniti Pool

Beautiful Sunset Villa is nestled in the heart of Chalk Sound, Providenciales where guests are guaranteed a home away from home experience. It enjoys unique trade winds in a private and safe community close to restaurants and the beach. Beautiful Sunset Villa provides views of the famous Chalk Sound turquoise waters, featuring a private Infiniti pool, extensive pool deck, a dedicate kitchen and dining area with full air conditioning. View the video below! https://youtu.be/13YyhYECZQA

Villa in Providenciales

4.95 out of 5 average rating, 108 reviews

Villa DelEvan 4D / 1-bedrm villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

Condo in Providenciales

4.92 out of 5 average rating, 115 reviews

Romantic Escape with Stunning Pools & Sunset Views

Welcome to our private island paradise. This is a light, charming, one bedroom unit in a quiet setting with a view over the terraced pools & into Turtle Cove & the marina. Its 1091 square feet bring a spacious open plan living/dining/kitchen/balcony where you will particularly appreciate the new Bosch appliances. The patio door opening spans 16 feet. The large bedroom has a king size bed, walk-in closet, another TV, & a beautiful ensuite bath w/ a roomy walk-in shower.

Guesthouse in Long Bay Hills

4.99 out of 5 average rating, 152 reviews

Juba Sunset

Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Condo in Wheeland Settlement

4.95 out of 5 average rating, 114 reviews

Couple’s Retreat with ocean views and hot tub!

Free cancellation! Oceanside oasis with pool, ocean and garden views. Escape to the pristine blue waters at Northwest Point. Pool, ocean and hot tub within steps of condominium. Free access to kayaks and SUPs, snorkel gear, owners beach chairs, loungers and miles of secluded beach for walking, exploring or beachcombing. Airport is appoximately a 15 minute drive from Northwest Point Condominiums (formerly Northwest Point Resort).

Loft in Long Bay Hills

4.87 out of 5 average rating, 151 reviews

Best deal on island! On the water w/pool!

♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders.

Cottage in Cooper Jack Bay Settlement

4.86 out of 5 average rating, 139 reviews

The Breeze House , canal front and private pool

Our house has a fantastic constant breeze. We are right on the canal front making it a great place to kayak from. We are centrally located in Providenciales , The supermarket is just 10 minutes away, Grace Bay is 10 minutes away. very private. We have kayaks for your use . A/ C in all bedrooms plus fans in every room . Such a Peaceful location. 3 Bedrooms and 2 bathrooms making it a perfect family space for your vacation

Vacation rentals for every style

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Villas

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Popular amenities for Leeward Settlement waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Rental unit in Providenciales

4.93 out of 5 average rating, 56 reviews

Sunny Daze - Condo By the Water

Rental unit in Venetian Road Settlement

4.93 out of 5 average rating, 98 reviews

OCEAN ORCHID

Rental unit in The Bight Settlement

4.88 out of 5 average rating, 8 reviews

Oceanview Studio: Steps away to Grace Bay Beach

Rental unit in Providenciales

5 out of 5 average rating, 10 reviews

2 Bdrm, Stunning Marina View | On The Water

Private room in Grace Bay

4.94 out of 5 average rating, 16 reviews

Balcony room at Ital Retreat

Rental unit in Providenciales

4.67 out of 5 average rating, 30 reviews

Precious Lodging

Rental unit in Providenciales

4.93 out of 5 average rating, 42 reviews

Clean and Private Apartment near Beach, Golf, Food

Waterfront house rentals

Home in Venetian Road Settlement

4.94 out of 5 average rating, 17 reviews

Brighter Days Villa

Home in Long Bay Hills

4.97 out of 5 average rating, 33 reviews

Private water front villa – 5 mins from Grace Bay!

Home in Providenciales

4.95 out of 5 average rating, 22 reviews

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

Home in Providenciales

5 out of 5 average rating, 34 reviews

Private beach, Pool & Master Suite

Home in Providenciales

5 out of 5 average rating, 13 reviews

TC Villas -Sea Edge Villa -Romantic & Luxurious

Home in Long Bay Hills

4.97 out of 5 average rating, 37 reviews

Caribbean Villa with Pool and Beach Access

Home in Providenciales

4.87 out of 5 average rating, 63 reviews

Villa View - Sapodilla Beach & Chalk Sound

Home in Providenciales

4.97 out of 5 average rating, 37 reviews

Coastal Vibes Villa Near Sapodilla Beach

Waterfront condo rentals

Condo in Grace Bay

4.89 out of 5 average rating, 53 reviews

BEACH FRONT on Grace Bay Gorgeous 1 bedroom 2 bath

Condo in The Bight Settlement

4.87 out of 5 average rating, 53 reviews

Ocean view paradise

Condo in Wheeland Settlement

4.9 out of 5 average rating, 20 reviews

Ocean and Pool Front 2 Bedroom 2 Bath Condo

Condo in Grace Bay

4.93 out of 5 average rating, 28 reviews

Grace Bay Beach Front 2 BDR/ 2BTH Condo

Condo in Providenciales

5 out of 5 average rating, 17 reviews

Luxury Condo Somerset on Grace Bay!

Condo in The Bight Settlement

4.94 out of 5 average rating, 89 reviews

Coral Condo on Grace Bay Beach

Condo in Providenciales

4.84 out of 5 average rating, 25 reviews

Luxury Large 2 Bed 2 Bath at the Yacht Club

Condo in Providenciales

4.97 out of 5 average rating, 68 reviews

The Yacht Club-Relaxed Vibe-1 BR-Pool-Beach

Quick stats about waterfront rentals in Leeward Settlement

Total rentals
50 properties
Nightly prices starting at
$190 before taxes and fees
Total number of reviews
860 reviews
Family-friendly rentals
50 properties are a good fit for families
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore