Vacation rentals with a kayak in Leeward

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Top-rated kayak rentals in Leeward

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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

4.85 out of 5 average rating, 144 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, 102 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, 138 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, 115 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.

Guest favorite

A golf cart is parked on sandy terrain near the beach. It features a beige exterior and two seats, with colorful towels laid out on the back. Palm trees and turquoise water are visible in the background, creating a serene coastal setting.

Villa in Long Bay

4.88 out of 5 average rating, 65 reviews

Hakuna Matata Villa + Golf Cart!

Hakuna Matata Villa is a three-bedroom, three-bath home located in Long Bay on the south side of Providenciales. Our stylish golf cart offers a quick and fun way to access Long Bay Beach, located just two minutes away from Hakuna Matata Villa. The giant swimming pool of the Caicos Bank features miles of shallow warm turquoise water. Hakuna Matata Villa offers fantastic value for your money with close proximity to the shops and amenities of Grace Bay and Blue Haven Marina where many boat

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

The image shows a sandy beach area leading to clear turquoise waters. Two wooden loungers are positioned on the shore beside a small table with flowers. A bright yellow kayak rests on the sand, while a dock and villa are visible in the background, framed by lush greenery.

Villa in Providenciales

4.92 out of 5 average rating, 66 reviews

Rockspray Villa | On Point in Ocean | Waterfront |

Rock Spray is a delightfully unique Turks & Caicos private, single family vacation rental villa. She is set alone on a peninsula surrounded on three sides by the stunning turquoise waters of Chalk Sound. Of timeless beauty, Rockspray is designed with architectural genius and Caribbean excellence. The first in the Turks & Caicos Islands to be built of our native limestone and solid concrete, Rockspray, a two bed, two bath beauty, was featured in several prominent Caribbean magazines.

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, 122 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 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

4.92 out of 5 average rating, 128 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).

Guest favorite

A brown and white dog sits on the sandy beach, with its ears perked and mouth open in a relaxed expression. The water glimmers in the background, reflecting the blue sky and scattered clouds. The tranquil beach scene is enhanced by gentle waves lapping at the shore.

Apartment in Providenciales

4.96 out of 5 average rating, 243 reviews

The Old Beach House 2 bedroom

We have two Garden apartments downstairs that we renovated. One two bedroom two bathroom, and one 1 bed 1 bathroom. Just a 3 minute walk from a white sandy beach. You can walk to Da Conch shack restaurant along the beach in 5-10 minutes. Off the beaten trail. We live upstairs with our our potcake Boxer. We are so sad to say we just lost our legend Buster who you would have read about in all of our reviews.

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, 186 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!

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, 170 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.