Vacation rentals with a kayak in Leeward Settlement

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Top-rated kayak rentals in Leeward Settlement

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Superhost

An aerial view captures the villa nestled among tropical vegetation, with the serene turquoise waters of Taylor Bay and a pristine white sand beach stretching along the coastline. The surrounding landscape features a winding road and nearby villas, offering a sense of seclusion.

Villa in Providenciales and West Caicos

4.84 out of 5 average rating, 138 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

Top guest favorite

Two inflatable paddleboards with colorful designs are positioned beside a serene private pool. The area is surrounded by lush greenery, providing a natural ambiance. The clear blue water of the pool reflects the sunlight, creating a vibrant atmosphere for leisure activities.

Villa in The Bight Settlement

4.98 out of 5 average rating, 127 reviews

Grace Bay villa | Pool | 3min walk to Beach & Reef

A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

Guest favorite

A bright yellow kayak glides across calm, turquoise waters. Two people are seen paddling, surrounded by a serene seascape that reflects the blue sky. The composition highlights a peaceful outdoor activity, showcasing the accessibility of water adventures available at the property.

Apartment 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.

Superhost

The living room features a neutral color palette with light wood accents and high ceilings. Two sets of sliding glass doors provide access to the wrap-around balcony. Seating options include a leather sofa and two wooden chairs beside a glass coffee table, with a television mounted on a console.

Home in Providenciales

4.91 out of 5 average rating, 107 reviews

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views

Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this spacious, private, 2-Bedroom\2-Bathroom unit can accommodate up to 6 guests, with a king size bed, 2 full size beds, and a queen sofa bed. It occupies 2nd and 3rd floor of our middle building, roughly 15 yards from the pool, no pool view. With beautiful scenic views of the ocean and Long Bay Beach area, from its 3rd floor Livingroom and wrap-around balcony.

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 favorite

Guesthouse in Bottle Creek

4.9 out of 5 average rating, 97 reviews

Creek View Cottage on beautiful Bottle Creek

This Eco-friendly bungalow is close to the iron shore edge of Bottle Creek on NORTH CAICOS. Just minutes from sandy beaches, restaurants, grocery stores & liquor store. You’ll love the view of Bottle Creek & we are just a few hundred steps from the crystal clear water. Perfect for swimming, kayaking or bonefishing. Couples, fishermen & solo travelers will love it. A studio with king size bed, private bath & outdoor shower. There is no kitchen. Kayaks and snorkel gear included.

Superhost

A modern villa is framed by lush greenery, located near the shore. Kayaks in vibrant colors are positioned on the sandy beach, while steps lead from the villa to the water, creating an inviting connection to the outdoor environment.

Villa in Providenciales

4.91 out of 5 average rating, 58 reviews

Vista Cove - Entire Property

Vista Cove is a beautifully appointed 2 bedroom detached Villa designed by a very reputable local architect. Nestled at the bottom of the hill in the quiet area of Chalk Sound, Vista Cove provides a feeling of privacy and tranquility that can match any super high end Villa property for a fraction of the cost. It is a few minutes walk away from one of the peaceful Taylor Bay beach and is filled with all the amenities one needs for a great vacation of relaxation and adventure.

Guest favorite

A serene beachfront scene showcases two yellow lounge chairs positioned under white umbrellas. The calm turquoise waters are framed by a clear blue sky, with fluffy white clouds dotting the horizon. Native greenery and sandy pathways lead to the water's edge.

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.

Superhost

A sandy pathway leads down wooden steps towards the calm waters of Chalk Sound. Lush greenery frames the scene, while white cottages with sloped roofs are visible in the background against a clear blue sky.

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 favorite

Condo 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).

Superhost

A private dock extends into the clear blue waters, accompanied by a sandy path leading to a multi-level white home surrounded by green vegetation. Plush lounge chairs are arranged on the dock, inviting relaxation under the clear sky.

Villa in Providenciales

4.82 out of 5 average rating, 11 reviews

Tres Vistas, Caribbean, TCI

Enjoy breathtaking ocean views from this four-tiered home's multi-level deck and indoor/outdoor living space. This property in Turks and Caicos boasts unparalleled views and a private dock and sandy beach for launching watercraft into Silly Creek for SUPs or kayaking. A 15-minute walk will take you to Taylor Bay, known for its stunning white sand beach and calm, crystal-clear blue waters.

Top guest favorite

Home in TC

4.98 out of 5 average rating, 179 reviews

“The Lighthouse”, Private Pool, Ocean Views, Beach

The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!