
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 £222 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.

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.

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.

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.

Private Romantic Beachfront Getaway!
This is bungalow #11 (see numbered aerial photo). It 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 ocean—ideal for lounging, dining, or enjoying the sunrise. The private fire pit provides a cozy, unforgettable experience under the stars. Private and peaceful, this bungalow is your personal escape to paradise.

“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.

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.

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.

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.

Hakuna Matata Villa
Hakuna Matata Villa is a three-bedroom, three-bath home located in Long Bay on the south side of Providenciales. and just a 2-minute drive from Long Bay Beach. 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 trips and watersports activities are based.

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!

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.

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!
Popular amenities for kayak rentals in Leeward
House rentals with a kayak

Casa de Isle, Taylor Bay, Chalk Sound area

Brighter Days Villa

Bright Idea Beachfront Villa

Beach Escapes - Villa One

Panoramic Turquoise Views Villa 1

Canal Front 4 Bedroom Villa in Leeward settlement

Coastal Vibes Villa Near Sapodilla Beach

Peaceful 1BR Private Cottage w/ HotTub Beach Front
Other holiday rentals with a kayak

Exhale Villa – Modern Luxury with Stunning Views

Tres Vistas, Caribbean, TCI

Newly Renovated 2 Bedroom/2 Bath Beach Front Condo

Ocean and Pool Front 2 king beds 2 Bath Condo

Beautiful 3 Bed/2 Bath Oceanview Beachfront Resort

Waterfront 3BR Villa w/ Pool, Canal View , Parking

Covered Balcony, Beach Front,3 Bed/3 Bath, Hot Tub

Villa Do Little - Near Grace Bay + Long Bay Beach
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