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.

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Top guest favourite
The modern villa features a two-story design with a spacious ground-level patio. A private pool reflects the blue sky, surrounded by tropical landscaping. Comfortable outdoor seating is visible on the terrace, offering a quiet space for relaxation.
Villa in The Bight Settlement
4.98 out of 5 average rating, 144 reviews

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.

Guest favourite
A bright dining area overlooks the marina, featuring a table with chairs positioned for scenic views. Lush greenery frames the outdoor space, while the tranquil blue water reflects the clear sky. The room is designed with floor-to-ceiling glass doors that enhance the open layout.
Flat in Venetian Road Settlement
4.94 out of 5 average rating, 115 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.

Guest favourite
A serene beach scene features soft white sand leading to calm waters, with lounge chairs placed under umbrellas. The tranquil sky displays a gradient of pastel colors as the sun sets, illuminating the nearby condominium and surrounding palm trees.
Apartment in Wheeland Settlement
4.92 out of 5 average rating, 128 reviews

Holiday discount- 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, sofa, tables, and new TV added October 2025!

Superhost
The living room features a neutral color palette with light wood accents and high ceilings. Two sets of sliding glass doors provide access to the wrap-around balcony. Seating options include a leather sofa and two wooden chairs beside a glass coffee table, with a television mounted on a console.
Home in Providenciales
4.89 out of 5 average rating, 113 reviews

Sea La Vie - Beachside 2 bdr Unit #4, 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.

Top guest favourite
A tranquil beach scene shows soft, sandy shores meeting clear turquoise waters under a partly cloudy sky. Gentle waves lap at the shoreline, while palm trees and distant structures provide a glimpse of the local environment. A wooden pier is visible in the background.
Flat in Providenciales
4.99 out of 5 average rating, 106 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.

Guest favourite
An overhead view reveals a private pool bordered by a patio with lounge chairs and outdoor seating, complemented by lush greenery. Nearby, a sandy beach leads to two kayaks resting beside the water, all under the shade of palm trees.
Home in Providenciales
4.93 out of 5 average rating, 56 reviews

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.

Top guest favourite
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales
4.99 out of 5 average rating, 118 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.

Guest favourite
A modern villa is showcased with a sleek design and expansive outdoor space. A clear swimming pool reflects the surrounding landscape. Chaise lounges are arranged along the pool terrace, while a shaded dining area with a large table is visible in the background.
Villa in Long Bay Hills
4.94 out of 5 average rating, 17 reviews

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.

Guest favourite
Villa in Providenciales and West Caicos
4.85 out of 5 average rating, 145 reviews

Secluded 3 BR Villa on Taylor Bay -Place De La Sol

The luxury of privacy is what this villa is all about. A few steps through a private tropical path takes you to the pristine waters and powder sand beach that is Taylor Bay. This Villa is split between the main villa which hosts 2 bedrooms, living room, bathroom and kitchen/dining. The primary suite is located across the patio with it's private bathroom and outdoor/indoor shower. Sunsets on Taylor Bay are the best on the island! **12% TCI Tax Included

Guest favourite
A golf cart is parked on sandy terrain near the beach. It features a beige exterior and two seats, with colorful towels laid out on the back. Palm trees and turquoise water are visible in the background, creating a serene coastal setting.
Villa in Long Bay
4.88 out of 5 average rating, 66 reviews

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.

Guest favourite
An infinity pool glistens under a clear blue sky, with lounge chairs positioned elegantly at the water's edge. The tranquil waters of Chalk Sound are visible in the background, reflecting the vibrant hues of the ocean and the distant shoreline.
Home in Providenciales
4.89 out of 5 average rating, 35 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 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!

Top guest favourite
The image captures the exterior of a cottage at dusk, highlighting a lighthouse-shaped tower with softly illuminated windows. A poolside area is visible, featuring lounge seating and a dining area, all surrounded by white walls and a well-maintained patio space.
Home in TC
4.98 out of 5 average rating, 191 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!

Popular amenities for kayak rentals in Leeward

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 £202 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 & child-friendly amenities

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 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!