Waterfront holiday rentals in Leeward Settlement

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Top-rated waterfront rentals in Leeward Settlement

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Guest favourite

Flat in Venetian Road Settlement

4.93 out of 5 average rating, 107 reviews

OCEAN ORCHID

This fabulous penthouse apartment is located within the exclusive Turtle Tail Marina and next to the late singer Prince's house. This newly built 3 large en suite bedroom apartment offers beautiful ocean and marina views from every room and balconies. The outdoor BBQ area has views of the ocean and Flamingo Lake where you can socialize, chill and spot the odd pink flamingo. There is a large pool with loungers and a hammock for relaxing, kayaks are available to explore the small cays and beach.

Top guest favourite

Guest house in Bottle Creek

5 out of 5 average rating, 8 reviews

Water’s Edge Studio

Completely unwind at this unique and tranquil piece of undiscovered paradise. Water’s Edge Guest Studio is ideal for people who want to simply relax in nature or enjoy an adventurous week exploring Bottle Creek, North and Middle Caicos. Water’s Edge sits on 5 acres with stunning views of Bottle Creek and pathways that meander down to the water front. Kayaks, paddle boards, beach chairs and snorkel gear are provided. Ferry runs 3-5 times daily and flights MWF, to and from Providenciales

Superhost

Flat in Providenciales

4.91 out of 5 average rating, 182 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

Superhost

Villa in Caicos Islands

4.63 out of 5 average rating, 8 reviews

Sweet Escape Villa Waterfront Kayak + SUV BOAT Opt

Sweet Escape is centrally located on the Discovery Bay/Cooper Jack Bay Canal System. South Side Marina, The Wymara Villas and Cooper Jack Bay beach are at the mouth of the marina. Our spacious two storey villa has a vaulted caribbean wood beam ceiling. A number of beautiful furniture pieces were imported to make our villa a true dream home. 2 Queen Slip Cover Sofa's and a Stanley Indoor Chaise Lounge are so comfortable your family will melt into them, so Relax & Enjoy Island Life.

Guest favourite

Villa in Providenciales

4.95 out of 5 average rating, 119 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.

Guest favourite

Apartment in Providenciales

4.91 out of 5 average rating, 125 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.

Top guest favourite

Guest house in Long Bay Hills

4.99 out of 5 average rating, 170 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.

Superhost

Flat in Caicos Islands

4.84 out of 5 average rating, 139 reviews

Palm Point Loft - Waterfront Canal

Palm Point Loft is the perfect spot for you to come and experience the peace and beauty of Providenciales. Located canal side, this private and spacious 2 bedroom second floor apartment is centrally located, 5 mins to Grace Bay Beach, restaurants and grocery stores. The unit is airy and bright offering a private sanctuary for guests to relax on their own balcony - the perfect place to unwind and enjoy the gentle breeze off the water while watching the sunset.

Superhost

Cottage in Providenciales

4.8 out of 5 average rating, 5 reviews

Swan Cottages

This charming pair of newly renovated waterfront cottages with a brand new 28-foot pool is a 2-minute walk from the scenic Sopadilla Bay Beach and Las Brisas Restaurant and walking distance to the exclusive Taylor Bay Beach. Located directly on the Chalk Sound National Park with views of its breathtaking blue waters, this beautiful, idyllic location is perfect for kayaking and paddle boarding. Rare sightings of dolphins have been made in this area.

Guest favourite

Apartment in Wheeland Settlement

4.95 out of 5 average rating, 121 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).

Guest favourite

Loft in Long Bay Hills

4.88 out of 5 average rating, 170 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.

Top guest favourite

Apartment in Caicos Islands

4.95 out of 5 average rating, 19 reviews

2 Bdrm Garden & Marina View at The Yacht Club | C4

This fully refurbished 2000 SF two bedroom condo is located in a gated community, This unit is located on the ground floor. Walk out to beautiful landscape gardens, a marina view and to the pool. It has a full kitchen. There is a coffee maker, kettle, and toaster. It is stocked with flatware, glassware, and linens. There is a bluetooth speaker as well. For the beach & pool there are towels, chairs, umbrella & cooler.