Holiday rentals with a kayak in Leeward

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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, 163 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, 119 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, 116 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.

Superhost
Villa in Leeward Settlement
5 out of 5 average rating, 3 reviews

Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks

Classic Caribbean 3 Bedroom canal front villa in Leeward. Cotton House has been designed in the timeless, traditional Caribbean aesthetic and is solar powered. Located in the gated Leeward community (25 min from PLS airport - 8 min to Grace Bay), this canal front home exudes an easy living elegance. Each bedroom opens to a central courtyard, the serene heart of the home featuring fountain, ferns, climbing vines, and tropical trees. *Ask us about our 4 and 5 Bedroom options for this villa.

Superhost
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
4.86 out of 5 average rating, 74 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

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
4.89 out of 5 average rating, 120 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.

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, 110 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.

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, 132 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
Villa in Providenciales, Long Bay Beach
4.91 out of 5 average rating, 32 reviews

Premier Seaside Villa with Pool at White Villas (7

WHITE VILLAS (7) is a modern 2-bedroom, 3-bathroom retreat just a 3-minute walk from Long Bay Beach and 5 minutes from Grace Bay. Sleeping up to 6, 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.

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
4.89 out of 5 average rating, 47 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!

Superhost
A two-story villa is positioned at the edge of Flamingo Lake, surrounded by lush greenery. A wrap-around deck extends around the upper level, providing a panoramic view of the water. The clear blue sky reflects in the tranquil lake, enhancing the serene landscape.
Home in Venetian Road Settlement
4.78 out of 5 average rating, 45 reviews

Brighter Days Villa

3-bedroom, 2-bathroom villa in Turtle Tail with a private beach on Flamingo Lake and walking distance to the South shore. Incredible wrap-around deck, spacious open-plan kitchen and living area, large glass sliding doors overlooking the lake provide breathtaking views from all angles. All rooms offer views over the North waterfront and South shore. A one-person kayak and four stand-up paddleboards are included.

Top guest favourite
Flat in Providenciales
4.96 out of 5 average rating, 274 reviews

The Old Beach House 2 bedroom, 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.

Popular amenities for kayak rentals in Leeward

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 £224 per night before taxes and fees

  • Verified guest reviews

    Over 650 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    50 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

  • 5 Average rating

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