
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 $524 NZD 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 and kid-friendly amenities

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Leeward holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Leeward rentals

4.9 Average rating
Leeward stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Accommodation with a Kayak in Leeward
Guests agree: these holiday homes with a kayak 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 gated 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.
Outdoor spacesValueSleep quality
4.98 out of 5 average rating, 170 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.
Outdoor spacesLocationBiking
4.94 out of 5 average rating, 122 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.
ValueOutdoor spacesHospitality
5.0 out of 5 average rating, 121 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.
LocationOutdoor spacesQuiet
5.0 out of 5 average rating, 25 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.
LocationOutdoor spacesGetting around
4.9 out of 5 average rating, 124 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.
ValueLocationHiking
4.98 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.
ValueOutdoor spacesView
4.99 out of 5 average rating, 144 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.
Outdoor spacesLocationPool
4.91 out of 5 average rating, 33 reviews
Hakuna Matata Villa - 5 Minutes to Long Bay Beach
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.
ValueOutdoor spacesAmenities
4.86 out of 5 average rating, 76 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!
ValueLocationView
4.91 out of 5 average rating, 54 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!
LocationOutdoor spacesAmenities
4.95 out of 5 average rating, 129 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.
LocationValueHospitality
4.95 out of 5 average rating, 336 reviewsPopular amenities for Leeward kayak rentals
Holiday House Rentals with a Kayak

*New* 3 Bedroom Waterfront Villa with Pool
Outdoor spacesLocationBeach
5.0 out of 5 average rating, 15 reviews
Brighter Days Villa
ValueLocationBeach
4.79 out of 5 average rating, 47 reviews
Peaceful 1BR Private Cottage w/ HotTub Beach Front
Outdoor spacesLocationPool
4.96 out of 5 average rating, 26 reviews
Casa de Isle, Taylor Bay, Chalk Sound area
LocationValueGetting around
5.0 out of 5 average rating, 77 reviews
Panoramic Turquoise Views Villa 1
Outdoor spacesLocationView
5.0 out of 5 average rating, 5 reviews
Sweet Escape Villa - Gated Waterfront w/Dock Kayak
LocationAccuracyNearby
4.73 out of 5 average rating, 11 reviews
Coastal Vibes Villa Near Sapodilla Beach
LocationOutdoor spacesCheck-in
4.95 out of 5 average rating, 60 reviews
*NEW Villa View-Walk2Beach-Pool-Kayaks-Chalk Sound
LocationAccuracyCondition
4.89 out of 5 average rating, 9 reviewsOther holiday rentals with a kayak

Villa Do Little - Near Grace Bay + Long Bay Beach
Outdoor spacesValueAccuracy
4.9 out of 5 average rating, 30 reviews
Corcus Plum villa
ValueLocationLaundry
4.97 out of 5 average rating, 70 reviews
StarFish Cottage 3Bedroom, 3.5 Bathroom
ValueLocationComfort
4.82 out of 5 average rating, 11 reviews
Waterfront Villa | Private Beach Cove & Pool
LocationValueFamily
4.89 out of 5 average rating, 83 reviews
Exhale Villa – Modern Luxury with Stunning Views
Outdoor spacesLocationHot tub
4.68 out of 5 average rating, 91 reviews
Beautiful Ocean View 3 Bedroom Condo on the Beach
ValueLocationPool
5.0 out of 5 average rating, 20 reviews
Ocean and Pool Front 2 king beds 2 Bath Condo
Outdoor spacesLocationDecor
4.92 out of 5 average rating, 36 reviews
Tres Vistas, Caribbean, TCI
Outdoor spacesLocationCheck-in
4.82 out of 5 average rating, 17 reviewsDestinations to explore
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