
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.

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.

“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.

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.

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

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.

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.

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.

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.

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!

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.

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
House rentals with a kayak

Turquoise Panoramic Views Villa 2

Casa de Isle, Taylor Bay, Chalk Sound area

Tropical Villa Paradise: Pool, Beach & 360° Views

Private 3 bed Island Home on the canal with pool

Tropical Chalk Sound Cottage with Pool and Kayak!

Coastal Vibes Villa Near Sapodilla Beach

Harbour House - 2 Bed Waterfront; 7 Min to Beach

Sweet Escape Villa Waterfront Kayak + SUV BOAT Opt
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Exhale Villa – Modern Luxury with Stunning Views

Tropical Paradise Beach Front Penthouse + Pool SUV

Your waterfront Dream Getaway Starts Here

Vista Cove 1 Bedroom Villa

Beautiful Ocean View 3 Bedroom Condo on the Beach

Apt with private pool and direct beach access

Beautiful 2 bed/2 bath Oceanview Beachfront Resort

Rockspray Villa | On Point in Ocean | Waterfront |
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!
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