
Holiday rentals with a kayak in Leeward
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Leeward
Guests agree: these rentals with 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 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.

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.

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

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.

Vista Cove - Entire Property
Vista Cove is a beautifully appointed 2 bedroom detached Villa designed by a very reputable local architect. Nestled at the bottom of the hill in the quiet area of Chalk Sound, Vista Cove provides a feeling of privacy and tranquility that can match any super high end Villa property for a fraction of the cost. It is a few minutes walk away from one of the peaceful Taylor Bay beach and is filled with all the amenities one needs for a great vacation of relaxation and adventure.

Villa DelEvan 4B / 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.

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!

The Old Beach House 2 bedroom
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!

Waterfront Turtle Tail Villa | Pool & Kayaks
Escape to Márohu, a private waterfront villa in Turtle Tail, Turks & Caicos, with a pool, sandy shore, and sweeping views over Flamingo Lake. Just 10 minutes from Grace Bay Beach, it’s the ideal retreat for families or friends looking for a peaceful, design-forward stay with easy access to the island’s best beaches, restaurants, and boating.

Sea La Vie - Beachside 4 Bedroom Villa, Unit #1
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.
Popular amenities for kayak rentals in Leeward
House rentals with a kayak

Casa de Isle, Taylor Bay, Chalk Sound area

Brighter Days Villa

Panoramic Turquoise Views Villa 1

Coastal Vibes Villa Near Sapodilla Beach

Peaceful 1BR Private Cottage w/ HotTub Beach Front

Sweet Escape Villa Waterfront Kayak + SUV BOAT Opt

Waterfront Villa | Private Beach Cove & Pool

Waterfront Paradise, Pool, Kayaks & 360 Views
Other holiday rentals with a kayak

Villa De Marco

Private 3 bed Island Home on the canal with pool

Oceanfront Penthouse Escape • Steps to Beach, Pool

Tropical Chalk Sound Cottage with Pool and Kayak!

Northwest Paradise - Gorgeous, Modern & Peaceful

3bd ~ Private Pool ~ Kayak to the Mangroves

Flamingo Lake Villa

Villa Do Little - Near Grace Bay + Long Bay Beach
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 £221 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!
Destinations to explore
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Santiago De Los Caballeros Holiday rentals
- Santo Domingo Este Holiday rentals
- Puerto Plata Holiday rentals
- Sosúa Holiday rentals
- Cabarete Holiday rentals
- Juan Dolio Holiday rentals
- Jarabacoa Holiday rentals
- Boca Chica Holiday rentals
- Río San Juan Holiday rentals
- Bonao Holiday rentals
- Rentals with a patio Leeward
- Rentals with pools Leeward
- Flat rentals Leeward
- Beachfront rentals Leeward
- Villa rentals Leeward
- Rentals with a firepit Leeward
- Rentals with outdoor seating Leeward
- House rentals Leeward
- Waterfront rentals Leeward
- Rentals with a washing machine and dryer Leeward
- Luxury rentals Leeward
- Family-friendly rentals Leeward
- Fitness-friendly rentals Leeward
- Rentals with a hot tub Leeward
- Rentals with beach access Leeward
- Pet-friendly rentals Leeward
- Rentals with a kayak Providenciales
- Rentals with a kayak Caicos Islands
- Rentals with a kayak Turks and Caicos Islands




