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Holiday rentals with a kayak in Leeward

Find and book unique kayak rentals on Airbnb

Quick stats about holiday rentals with a kayak in Leeward

  • Total holiday rentals

    Explore 60 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at £221 per night before taxes and fees

  • Verified guest reviews

    Over 760 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Leeward holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Leeward rentals

  • 4.9 Average rating

    Leeward stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with kayak in Leeward

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

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Top guest favourite
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, 169 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 favourite
A bright dining area overlooks the marina, featuring a table with chairs positioned for scenic views. Lush greenery frames the outdoor space, while the tranquil blue water reflects the clear sky. The room is designed with floor-to-ceiling glass doors that enhance the open layout.
Flat in Venetian Road Settlement
4.94 out of 5 average rating, 121 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 favourite
An aerial view captures the outdoor space at sunset, featuring a spacious pool and a hot tub. The surrounding greenery enhances the tranquil setting, while distant water vistas reflect the warm colors of the sky. Lounge chairs are positioned around the pool area for relaxation.
Villa in Long Bay Hills
4.9 out of 5 average rating, 30 reviews

Villa Do Little - Near Grace Bay + Long Bay Beach

4 BR, 4 Bath - Modern villa in beautiful Long Bay, mins away from kiteboarding, Long Bay beach, and dining. Rent EXCLUSIVELY, NO SHARING. Grace Bay is a 6 min drive. Perched 50 ft. from the water, enjoy kayaking or boating on the canal. Do Little is private, both the house and canal face West, providing romantic sunset views. Free WiFi, 2 kayaks, 1 fishing canoe, life vests, snorkel gear, ice cooler, beach chairs, and more. Outdoor shower, BBQ, Pool, Hot Tub. Please read the rate information.

Top guest favourite
The spacious bedroom features a king-size bed with striped bedding and a decorative pillow. A wall-mounted Smart TV is positioned across from a wooden desk and chair. Large sliding doors lead to a balcony, allowing natural light to illuminate the room, which has a vibrant blue floor design.
Guest house in Providenciales
5.0 out of 5 average rating, 121 reviews

“Sail Loft Port”, Duplex with a Pool, Beach Access

Sail Loft Port is the left side of our purpose-built guest duplex. Our Sail Loft duplex features two separate but identical efficiency suites, each one equipped with a King Sized bed, bath and kitchenette. The pool is shared with guests who may be staying in the other side. Wander down to the dock and use our SUPs and kayaks in the canal where you are guaranteed to see turtles. Fast WiFi lets you work from home if you must. Smart TVs with Netflix help you wind down after a day of fun.

Top guest favourite
An outdoor deck features a private pool surrounded by tropical foliage. Lounge chairs are positioned near a table shaded by a large umbrella. A view of beachside structures and palm trees can be seen in the background under a clear blue sky.
Flat in Long Bay Hills
5.0 out of 5 average rating, 24 reviews

Apt with private pool and direct beach access

Discover an intimate oasis perched just steps from the turquoise waters of Long Bay. Our newly added Oceanfront One-Bedroom Apartment at Swaying Palms offers the perfect blend of privacy, luxury, and resort-style amenities—ideal for couples, solo travelers, or anyone craving a secluded tropical retreat. This space features a full kitchen, private pool & spacious outdoor deck overlooking the turquoise sea. Your very own private umbrella/lounge chairs will be placed daily at the water's edge.

Guest favourite
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
4.9 out of 5 average rating, 124 reviews

Sea La Vie - #4 Beachside 2 bdr Suite, 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.

Top guest favourite
A tranquil beach scene shows soft, sandy shores meeting clear turquoise waters under a partly cloudy sky. Gentle waves lap at the shoreline, while palm trees and distant structures provide a glimpse of the local environment. A wooden pier is visible in the background.
Flat in Providenciales
4.98 out of 5 average rating, 137 reviews

Pelican View #4 amazing beach views

Pelican View apartments offers unrivalled beach access and a truly unique and tranquil way to experience Providenciales. Located in the neighbourhood of Blue Hills you’ll quickly be lulled into the local rhythm of island life. From Blue Hills it’s an easy 15 minute drive east to the heart of the tourist mecca of Grace Bay; if you travel west you’ll find the best national parks and nature reserves that Turks & Caicos has to offer, often overlooked gems in this island paradise.

Top guest favourite
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales
4.99 out of 5 average rating, 141 reviews

Villa DelEvan 4A / 1-bedrm Beach front 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
An infinity pool glistens under a clear blue sky, with lounge chairs positioned elegantly at the water's edge. The tranquil waters of Chalk Sound are visible in the background, reflecting the vibrant hues of the ocean and the distant shoreline.
Home in Providenciales
4.91 out of 5 average rating, 54 reviews

NEW Water Access! Luxe Villa, Infinity Pool& Views

Welcome to Maresia Villa — a luxury waterfront retreat in Turks & Caicos. ** NEW: direct water access with a kayak for guests use** Enjoy an infinity pool, rooftop terrace for stargazing, and breathtaking sunset views and Chalk Sound’s turquoise lagoon from every room. Just 1 minute drive from Sapodilla Bay beach, this villa is ideal for couples, families, or group of friends. SPECIAL OFFER: Stay 7+ nights and enjoy 10% off your booking!

Top guest favourite
A dining area is set on a wooden deck, featuring a white table surrounded by light blue cushioned chairs. A large blue umbrella provides shade while the scenic view of the turquoise water and lush greenery is visible in the background.
Villa in Providenciales
4.95 out of 5 average rating, 129 reviews

Villa Jayla

Villa Jayla is located on the south side of Providenciales approximately 1 mile from the famous sapadilla and Taylor bay beaches. the Beautiful Villa sits on the south side of the Island over looking the sound where you can go kayaking or chill and look at the beautiful sunset. We now have a paddle board!

Top guest favourite
A tranquil scene shows calm waters reflecting a clear blue sky. A lone bird is perched on a cluster of large rocks, surrounded by gentle waves. The serene setting highlights natural beauty and peacefulness, inviting a sense of relaxation and harmony.
Apartment in Providenciales
4.95 out of 5 average rating, 334 reviews

1 bedroom perfect for couples close to quiet beach

spacious 1 bedroom Garden Apartment is just a 3 minute walk to a white sandy beach. Just a 5 minute beach walk to da Conch Shack. The Beach is so quiet you hardly see anyone. The apartment is in a quiet residential area. It feels just like home.

Superhost
Home in Providenciales
4.87 out of 5 average rating, 39 reviews

2 bedroom Villa - Private Beach & Pool

This stunning Villa located in Silly Creek, an exclusive residential neighborhood on Providenciales. Located approximately 7 mile from the airport. This two-bedroom villa has its own private beach, pool and boat dock.

Popular amenities for kayak rentals in Leeward