Vacation rentals with a kayak in Leeward

Villa in Providenciales and West Caicos

An aerial view captures the villa nestled among tropical vegetation, with the serene turquoise waters of Taylor Bay and a pristine white sand beach stretching along the coastline. The surrounding landscape features a winding road and nearby villas, offering a sense of seclusion.

4.85 out of 5 average rating, 144 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 Master Suite is located across the patio with it's private bathroom and outdoor/indoor shower. Sunsets are 2nd to none and should be done at least once beachside since the villa faces west. **12% TCI Tax Included

Apartment in Providenciales

A small weathered boat is anchored gently in shallow water, positioned along a sandy beach. The clear turquoise sea stretches towards a blue sky with a few wispy clouds, creating a serene coastal scene.

4.93 out of 5 average rating, 107 reviews

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.

Villa in The Bight Settlement

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.

4.98 out of 5 average rating, 142 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.

Apartment in Venetian Road Settlement

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.

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 suite in Long Bay Hills

The modern kitchen features a central island with bar seating for three. A full suite of stainless steel appliances is complemented by white cabinetry and a striking blue accent wall. A cozy living area includes a plush armchair and a sleek coffee table, with natural light filling the space.

4.94 out of 5 average rating, 50 reviews

SunSeaSand 1Bdrm Seaside Unit B- Long Bay Hills

SunSeaSand, your premier boutique resort, offers a prime location just a brief 3-minute stroll away from the stunning Long Bay Beach and 5-minute joyride to Grace Bay's restaurants and resorts, positioning it as the destination in Turks and Caicos for your upcoming retreat. Whether you're seeking a romantic getaway, a memorable family vacation, or a trip with friends, SunSeaSand guarantees delight with our convenient location and thoughtful amenities—ensuring an effortless, pleasurable stay.

Condo in Wheeland Settlement

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.

4.92 out of 5 average rating, 128 reviews

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!

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.

4.93 out of 5 average rating, 55 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.

4.99 out of 5 average rating, 118 reviews

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

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.

Home in Cooper Jack Bay Settlement

5 out of 5 average rating, 15 reviews

Breeze Luxury 3 Br Waterfront Villa

Welcome to your dream getaway in Turks and Caicos! This stunning 3-bedroom, 2 bath luxury villa sits directly on the peaceful canal in the prestigious Cooper Jack community, just minutes from the world famous Grace Bay Beach. Luxury 3BR canal-front villa in Turks & Caicos with private pool, dock, full kitchen, ensuite baths, and minutes from Grace Bay Beach. Ideal for families or couples seeking upscale comfort, water access, and serene island vibes.

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.

4.88 out of 5 average rating, 34 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!

4.98 out of 5 average rating, 188 reviews

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

“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!

Guest suite in Providenciales

A spacious studio unit features a wooden queen bed with a light blanket and decorative pillows. Natural light enters through a set of glass doors, leading to a private patio. A small round table with bar stools complements the minimalist decor.

4.8 out of 5 average rating, 171 reviews

Sea La Vie - Beachside Studio Unit #3

Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this private Studio unit with it own private entry and patio, can accommodate up to 2 guests, with a queen size bed. It is located on the ground floor, roughly 15 yards from the pool. No pool view.

Popular amenities for Leeward kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Providenciales and West Caicos

A spacious wrap-around deck surrounds a private swimming pool, with tropical plants and colorful flowers adding natural beauty. Sun loungers and seating areas are available for relaxation. A shaded area with a hammock is visible, offering a serene spot to unwind.

5 out of 5 average rating, 66 reviews

Casa de Isle, Taylor Bay, Chalk Sound area

Home in Venetian Road Settlement

A two-story villa is positioned at the edge of Flamingo Lake, surrounded by lush greenery. A wrap-around deck extends around the upper level, providing a panoramic view of the water. The clear blue sky reflects in the tranquil lake, enhancing the serene landscape.

4.77 out of 5 average rating, 35 reviews

Brighter Days Villa

An aerial view captures the vibrant landscape, showcasing a property surrounded by lush tropical vegetation and the clear turquoise waters of Chalk Sound National Park. The home features multiple structures and is nestled against a rocky coastline, enhancing the serene coastal ambiance.

4.74 out of 5 average rating, 19 reviews

Tropical Retreat: 360° Views, Pool, Beaches Nearby

A bright living space displays a dining table with dark wood and plush seating. In the background, expansive glass doors frame a stunning view of turquoise waters and lush landscapes. A potted floral arrangement adds a touch of color to the serene setting.

4.96 out of 5 average rating, 48 reviews

Coastal Vibes Villa Near Sapodilla Beach

A charming villa is set against a bright blue sky, featuring a metal roof and landscaped gardens. The property is framed by tall palm trees and presents a waterfront view with crystal-clear turquoise water. A wooden pergola is visible near the entrance.

Home in Leeward Settlement

4.71 out of 5 average rating, 14 reviews

3bd ~ Private Pool ~ Kayak to the Mangroves

Home in Leeward Settlement

4.95 out of 5 average rating, 83 reviews

Guest House 2B&2B near Grace Bay Beach & Long Bay

4.83 out of 5 average rating, 6 reviews

A spacious outdoor patio features a wrap-around deck with seating, including cushioned armchairs and a dining area. A panoramic view of the ocean is visible beyond the infinity pool, framed by palm trees and a clear blue sky.

Home in NA

Villa Mariposa

4.7 out of 5 average rating, 10 reviews

A two-story villa is situated amidst lush tropical foliage. The building features a light-colored facade, large windows, and a staircase leading to the upper level. The surrounding sandy area is dotted with palm trees and greenery, creating a serene environment.

Home in Caicos Islands

Sweet Escape Villa Waterfront Kayak + SUV BOAT Opt

Cottage rentals with a kayak

Cottage in Providenciales

A sandy beach area leads to calm waters, surrounded by lush greenery. The scene features a clear blue sky with scattered clouds overhead. The gentle slope of the land guides visitors toward the water's edge, providing an inviting space for relaxation and outdoor activities.

4.84 out of 5 average rating, 19 reviews

Swan cottages #6 Waterfront

5 out of 5 average rating, 5 reviews

An aerial view depicts the Dragon Cay Resort, showcasing a collection of cottages surrounded by lush greenery and sandy paths. The turquoise ocean stretches in the background, with the coastline visible, enhancing the serene atmosphere of this tropical destination.

Cottage in Conch Bar

Cute tropical getaway cottage at Dragon Cay Resort

4.25 out of 5 average rating, 4 reviews

Aerial view of Dragon Cay Resort shows multiple cottages surrounded by lush greenery and coastal landscapes. Soft sandy paths connect the cottages, leading toward the vibrant blue ocean with gentle waves. The horizon features a clear sky, enhancing the serene setting.

Cottage in TC

Ridgetop Cottage for 2| Dragon Cay | Mudjin Harbor

Cottage in Providenciales

A spacious living and dining area is presented, featuring a light-colored sectional sofa adorned with decorative pillows. A glass dining table accommodates four chairs, while the kitchen area is equipped with essential appliances, including a refrigerator, stove, and microwave. Natural light enters through a nearby window.

4.95 out of 5 average rating, 38 reviews

Your waterfront Dream Getaway Starts Here

4.83 out of 5 average rating, 18 reviews

The covered patio features a dining table and a comfortable lounge area, with views of the beach through large arches. Palm trees and beach chairs are visible in the bright landscape, creating a serene coastal ambiance.

Cottage in Whitby

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

4.88 out of 5 average rating, 32 reviews

An aerial view reveals a serene landscape of several cottages with teal roofs nestled among lush greenery. The coastline is visible, featuring the contrasting blue hues of the ocean and a rugged shoreline, complemented by distant rocky outcrops and clear skies.

Cottage in Conch Bar

Cottage for 2 | Dragon Cay Resort | Mudjin Harbour

Cottage in Long Bay Hills

The spacious living area features vaulted ceilings and large windows, allowing natural light to illuminate the room. A gray sofa with decorative pillows and a coffee table are present, creating a comfortable seating area. The open layout connects to the kitchen and dining area in the background.

4.86 out of 5 average rating, 50 reviews

SunSeaSand 2Bdrm Seaside Cottage - Long Bay Hills

Cottage in Providenciales

A sandy pathway leads down wooden steps towards the calm waters of Chalk Sound. Lush greenery frames the scene, while white cottages with sloped roofs are visible in the background against a clear blue sky.

4.8 out of 5 average rating, 5 reviews

Swan Cottages

Other vacation rentals with a kayak

A spacious two-story villa is depicted, featuring a white exterior with blue accents. Lush greenery surrounds the property, and a pathway leads to the entrance. The building showcases multiple balconies and large windows, providing access to natural light.

Home in Cooper Jack Bay Settlement

Villa Serenity - (3-Bed Waterfront Villa)

An outdoor deck features a private pool surrounded by tropical foliage. Lounge chairs are positioned near a table shaded by a large umbrella. A view of beachside structures and palm trees can be seen in the background under a clear blue sky.

Apartment in Long Bay Hills

Apt with private pool and direct beach access

4.99 out of 5 average rating, 112 reviews

An outdoor area features a swimming pool bordered by sun loungers and a shaded seating area. Umbrellas provide shade, while lush greenery and ocean views create a serene environment. The clear water of the pool reflects the blue sky, enhancing the inviting space.

Villa in Providenciales

Villa DelEvan 4B / 1-bedrm villa

4.93 out of 5 average rating, 29 reviews

A modern resort building is framed by lush greenery and palm trees. Pathways lined with manicured shrubs lead to the entrance, set against a bright blue sky. Balcony spaces are visible on the upper levels, providing views of the surrounding tropical landscape.

Resort in Long Bay Hills

Stunning Life. Style Resort w/Garden View

4.84 out of 5 average rating, 104 reviews

A spacious living area features a mix of modern furnishings, including a dark leather sofa and two light-colored armchairs. A wooden coffee table sits at the center, accompanied by decorative items. Natural light enters through large windows, illuminating the cream-colored tile flooring. A staircase leads to the upper level.

Villa in Providenciales

Sea La Vie - Beachside 4 Bedroom Villa, Unit #1

Aerial view captures a beachfront resort condo set amidst lush greenery, with the turquoise ocean sparkling in the background. The white building showcases multiple balconies and large windows, providing a serene coastal environment just steps from the beach.

Vacation home in Wheeland Settlement

4.78 out of 5 average rating, 40 reviews

Beautiful 2 bed/2 bath Oceanview Beachfront Resort

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.