
Vacation rentals with a kayak in Leeward
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Leeward

Total vacation rentals
Explore 60 vacation rentals in Leeward

Nightly prices starting at
Leeward vacation rentals start at ﺩ.ﺇ 1,102 per night before taxes and fees

Verified guest reviews
Over 760 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Leeward vacation rentals include wi-fi 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 kayak rentals in Leeward
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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.

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.

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.

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.

White Villas - Villa Near Ocean + Private Pool (6)
WHITE VILLAS (6) 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 5, 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.

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.

“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!

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.

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 Leeward kayak rentals
House rentals with a kayak

*New* 3 Bedroom Waterfront Villa with Pool

Brighter Days Villa

Casa de Isle, Taylor Bay, Chalk Sound area

Panoramic Turquoise Views Villa 1

2 bedroom Villa - Private Beach & Pool

Coastal Vibes Villa Near Sapodilla Beach

Peaceful 1BR Private Cottage w/ HotTub Beach Front

New & Unique Villa Blue Top! Waterfront 2 Bedrooms
Other vacation rentals with a kayak

Apt with private pool and direct beach access

Corcus Plum villa

Villa Do Little - Near Grace Bay + Long Bay Beach

Elite Villa with Pool, Steps from the Beach (11)

Exhale Villa – Modern Luxury with Stunning Views

Waterfront Villa | Private Beach Cove & Pool

Modern Cottage with Chalk Sound Views

Beautiful Ocean View 3 Bedroom Condo on the Beach
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