Vacation rentals with a kayak in Leeward

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Top-rated kayak rentals in Leeward

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Guest favorite

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

4.85 out of 5 average rating, 143 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

A small weathered boat is anchored gently in shallow water, positioned along a sandy beach. The clear turquoise sea stretches towards a blue sky with a few wispy clouds, creating a serene coastal scene.

Apartment in Providenciales

4.93 out of 5 average rating, 103 reviews

Pelican View #3 unrivalled beach views

Pelican View apartments offers unrivalled beach access and a truly unique and tranquil way to experience Providenciales. Located in Blue Hills you’ll quickly be lulled into the local rhythm of island life as you sit on your 2nd floor terrace enjoying the spectacular views and listening to the waves crashing on shore. This 2-bed, 1-ba apartment is comfortably appointed with true up-cycled charm. Peppered throughout are some treasured vintage pieces to make it feel like your home away from home.

Top guest favorite

The modern villa features a two-story design with a spacious ground-level patio. A private pool reflects the blue sky, surrounded by tropical landscaping. Comfortable outdoor seating is visible on the terrace, offering a quiet space for relaxation.

Villa in The Bight Settlement

4.98 out of 5 average rating, 135 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 living area is furnished with a light-colored sofa and two teal chairs, offering views through large glass doors. Artwork adorns the white walls, and the inviting outdoor pool is visible beyond a spacious terrace, enhancing the room's airy feel.

Apartment in Venetian Road Settlement

4.94 out of 5 average rating, 113 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

A modern open-concept living space features a sleek kitchen with white cabinetry and a gray mosaic backsplash. The area includes a dining bar with white stools and a comfortable seating arrangement. Natural light fills the space through large sliding doors, showcasing a vibrant blue accent wall.

Guest suite in Long Bay Hills

4.94 out of 5 average rating, 34 reviews

SunSeaSand 1Bdrm Seaside Unit A- Long Bay Hills

SunSeaSand, your premier boutique resort, offers a prime location just a brief 3-minute stroll away from the stunning Long Bay Beach and 5-minute joyride to Grace Bay's restaurants and resorts, positioning it as the destination in Turks and Caicos for your upcoming retreat. Whether you're seeking a romantic getaway, a memorable family vacation, or a trip with friends, SunSeaSand guarantees delight with our convenient location and thoughtful amenities—ensuring an effortless, pleasurable stay.

Superhost

A tranquil outdoor area is highlighted by a spacious pool surrounded by sun loungers and tropical greenery. An inviting patio with a dining table and an umbrella provides shade, while large glass doors lead into the villa. Bright blue skies and soft clouds complete the serene setting.

Villa in Providenciales, Long Bay Beach

5 out of 5 average rating, 29 reviews

Perfect for 1 Couple - Villa w/Pool & Beach access

WHITE VILLA is a luxurious retreat located in Long Bay Beach (5 min. from Grace Bay). A 3-minute stroll takes you straight to the beach, equipped with chairs, kayaks and stand-up-paddle boards. With no current, no coral, no waves, and no danger, it’s absolutely perfect for beach lovers and kiteboarders. Our cluster of 10 villas allows us to offer services and amenities you’d normally only find in a 5-stars hotel. ps: This unit is White Villas co-owner's home that he rents out when is away.

Guest favorite

A modern villa is positioned near the water's edge, surrounded by lush greenery. Brightly colored kayaks rest on the sandy shoreline, inviting exploration of the serene lagoon. Large windows on the villa allow for ample natural light.

Guesthouse in Providenciales

4.75 out of 5 average rating, 16 reviews

Vista Cove 1 Bedroom Villa

Vista Cove 1 Bedroom is a beautifully appointed Villa. This listing is an offering of the main "1 Bedroom Unit". 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 the beautiful and peaceful Taylor Bay beach and is filled with all the amenities one needs for a great vacation of relaxation and adventure!

Guest favorite

An outdoor area features a swimming pool bordered by sun loungers and a shaded seating area. Umbrellas provide shade, while lush greenery and ocean views create a serene environment. The clear water of the pool reflects the blue sky, enhancing the inviting space.

Villa in Providenciales

4.99 out of 5 average rating, 111 reviews

Villa DelEvan 4B / 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 favorite

A serene beach scene features soft white sand leading to calm waters, with lounge chairs placed under umbrellas. The tranquil sky displays a gradient of pastel colors as the sun sets, illuminating the nearby condominium and surrounding palm trees.

Condo in Wheeland Settlement

4.95 out of 5 average rating, 125 reviews

Couple’s Retreat - ocean view, pool 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).

Top guest favorite

The image captures the exterior of a cottage at dusk, highlighting a lighthouse-shaped tower with softly illuminated windows. A poolside area is visible, featuring lounge seating and a dining area, all surrounded by white walls and a well-maintained patio space.

Home in TC

4.98 out of 5 average rating, 185 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!

Guest favorite

The modern two-story home is showcased from an aerial perspective, featuring large glass doors and a spacious deck surrounding a pool. The pool area is adorned with lounge chairs, and a private boat dock is visible along the turquoise waters, complemented by lush greenery.

Villa in Caicos Islands

5 out of 5 average rating, 14 reviews

18 Kelly Isle

18 Kelly Isle is a modern 3-bed, bright two-story canal front home in the coveted Leeward neighborhood. The clever 3,000 square foot layout maximizes indoor / outdoor living within this beautiful vacation home. Enjoy wonderful views form the upper balcony and relax by the pool or the boat dock savoring the gentle warm breeze and ripple of the turquoise waters.

Superhost

A spacious studio unit features a wooden queen bed with a light blanket and decorative pillows. Natural light enters through a set of glass doors, leading to a private patio. A small round table with bar stools complements the minimalist decor.

Guest suite in Providenciales

4.8 out of 5 average rating, 168 reviews

Sea La Vie - Beachside Studio Unit #3

Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this private Studio unit with it own private entry and patio, can accommodate up to 2 guests, with a queen size bed. It is located on the ground floor, roughly 15 yards from the pool. No pool view.