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

Couple’s Retreat - ocean view, pool and hot tub!
Free cancellation! Oceanside oasis with pool, ocean and garden views. Escape to the pristine blue waters at Northwest Point. Pool, ocean and hot tub within steps of condominium. Free access to kayaks and SUPs, snorkel gear, owners beach chairs, loungers and miles of secluded beach for walking, exploring or beachcombing. Airport is appoximately a 15 minute drive from Northwest Point Condominiums (formerly Northwest Point Resort). New refrigerator and new TV added October 2025!

3 Bed Beach Oasis on Flamingo Lake w/Private Pool
Márohu is a stunning 3-bedroom modern Caribbean villa set within the exclusive neighbourhood of Turtle Tail, just a 10-minute drive from the world-renowned Grace Bay Beach. This spacious, well-equipped, and family-oriented villa offers expansive floor-to-ceiling views over Flamingo Lake from every room. You’ll experience the best of outdoor living with our own pool and sandy beach, ideal for lounging, a friendly game of cornhole, or exploring the lake with our included kayaks.

Villa DelEvan 4B / 1-bedrm 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 + Golf Cart!
SEASONAL UPDATE: Enjoy a magical tropical Christmas at Hakuna Matata Villa. Our guests in the month of December will be welcomed with holiday decor ensuring that cozy feeling, even when it's 80 degrees outside! 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.

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 guest 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 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 - 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.

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
Holiday House Rentals with a Kayak

Casa de Isle, Taylor Bay, Chalk Sound area

Brighter Days Villa

Tropical Retreat: 360° Views, Pool, Beaches Nearby

Villa Serenity - (3-Bed Waterfront Villa)

Canal-front 4BR Villa in Leeward settlement

Coastal Vibes Villa Near Sapodilla Beach

Aventine Villa

3bd ~ Private Pool ~ Kayak to the Mangroves
Cottages with a kayak

Swan cottages #6 Waterfront

Cute tropical getaway cottage at Dragon Cay Resort

Ridgetop Cottage for 2| Dragon Cay | Mudjin Harbor

Your waterfront Dream Getaway Starts Here

Caicos Cottage, 2 bdrm/2 bath beachfront w/pool

Cottage for 2 | Dragon Cay Resort | Mudjin Harbour

SunSeaSand 2Bdrm Seaside Cottage - Long Bay Hills

Swan Cottages
Other holiday rentals with a kayak

Sea La Vie - Beachside Studio Unit #3

Perfect for 1 Couple - Villa w/Pool & Beach access

Pelican View #4 amazing beach views

Sea La Vie - Beachside 1 bedroom Unit #6

Apt with private pool and direct beach access

“Sail Loft STBD”, Duplex with a Pool, Beach Access

Stunning Life. Style Resort w/Garden View

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views
Quick stats about holiday rentals with a kayak in Leeward

Total holiday rentals
Explore 50 holiday rentals in Leeward

Nightly prices starting at
Leeward holiday rentals start at $416 AUD per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

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

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

5 Average rating
Leeward stays are highly rated by guests—averaging 5 out of 5!
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