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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 £223 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, 166 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, 120 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
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 out of 5 average rating, 119 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.

Guest favourite
A cozy seating area is viewed from the inside of the palapa, featuring a comfortable white sofa. In the background, palm trees sway gently against the vibrant turquoise water, creating a calming seaside atmosphere. The expansive horizon meets the sky, enhancing the serene surroundings.
Villa in Long Bay Hills
5 out of 5 average rating, 7 reviews

New Oceanfront 2-Story Bungalow!

This bungalow (#10) provides the perfect blend of luxury and island living. Steps from the turquoise waters, it features a full kitchen, king-size bed, outdoor shower, and a cozy living area. The highlight is a stunning two-story palapa overlooking the shoreline—ideal for lounging, dining, or enjoying the sunrise. The private fire pit provides a cozy, unforgettable experience under the stars. Private, peaceful, and designed for relaxation, this bungalow is your personal escape to paradise.

Guest favourite
A view from the property shows a sandy area beside a quiet road that leads to the beach. Green foliage and tall pine-like trees frame the scene, with the sparkling blue ocean visible in the distance under a clear sky.
Flat in Providenciales
4.94 out of 5 average rating, 114 reviews

Pelican View #1 ground floor beachfront apartment

Pelican View apartments offer 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 as you sit on your ground floor terrace enjoying the spectacular views, listening to the waves crashing on shore, and planning which amazing local restaurant to enjoy for dinner. Watch the pelicans flying low across the water and the Osprey surveying his beach.

Guest favourite
Villa in Long Bay Hills
5 out of 5 average rating, 5 reviews

Elegant Villa with Pool, Steps from the Beach (13)

WHITE VILLAS (13) is a modern 3-bedroom, 4-bathroom retreat just a 3-minute walk from Long Bay Beach and 5 minutes from Grace Bay. Sleeping up to 8 (6 adults + 2 kids), it combines the privacy of a luxury villa with resort-style amenities. Integrated in the 15-villa WHITE VILLAS collection, it offers the upscale comforts and personalized service of a 5-star hotel—without the crowds or compromises. Ideal for beach lovers seeking space, style, and barefoot luxury in Turks & Caicos.

Top guest favourite
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
4.96 out of 5 average rating, 151 reviews

Villa DelEvan 4D / 1-bedroom 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
4.9 out of 5 average rating, 50 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 serene beach scene is depicted, featuring soft, white sand gently meeting clear turquoise waters. Lush greenery lines the shore, and a clear blue sky with scattered clouds enhances the peaceful atmosphere. The shoreline extends into the distance, inviting exploration.
Flat in Providenciales
4.96 out of 5 average rating, 277 reviews

2 bedroom, 2 bathrooms, garden, beach 2 mins walk

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.

Superhost
A spacious living area features a mix of modern furnishings, including a dark leather sofa and two light-colored armchairs. A wooden coffee table sits at the center, accompanied by decorative items. Natural light enters through large windows, illuminating the cream-colored tile flooring. A staircase leads to the upper level.
Villa in Providenciales
4.84 out of 5 average rating, 108 reviews

Sea La Vie - #1 Beachside 4-Bedroom Villa

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, 3800 sqft, 2 story, 4 bedroom/3 bathroom unit is right next to the pool, and can accommodate up to 10 guests, with 2 king size beds, 2 queen size beds, and a queen size sofa bed.

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, 127 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!

Guest favourite
A modern two-story structure features a clean white exterior with large windows allowing natural light. A wooden front door is centrally positioned, surrounded by tropical landscaping and well-maintained stone pathways. A clear blue sky serves as the backdrop.
Home in TC
4.92 out of 5 average rating, 26 reviews

Harbour House - 2 Bed Waterfront; 7 Min to Beach

Welcome to Harbour House, your warm, inviting, canal front escape. A unique, modern, island-fusion styled waterfront experience like no other! 12% Government Tax is calculated in final payment. Follow @islehavenpropertiestci Tag #islehaventci

Popular amenities for kayak rentals in Leeward