Vacation rentals with a pool in Canaan

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Canaan

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious pool area is highlighted by a clear blue pool, surrounded by sun loungers. The villa's exterior features large windows and is complemented by a covered patio with comfortable seating for relaxation. Lush greenery is visible along the property line.

Villa in Canaan

4.94 out of 5 average rating, 33 reviews

Cardinal Villas Tobago-Bram Villa, Samaan Grove

Our Villa is located in the gated community of Samaan Grove Tobago. One of the few gated communities. The villa itself is comfortable and spacious and just feels like a home away from home. The surroundings are lush and peaceful with birds chirping and beautiful greenery. Our outdoor patio invites you to unwind and relax and have fun pool days with family and kids absolutely love it. Finally connect to our Bluetooth fan lights on our patio, and enjoy your favorite playlist while enjoying the company of your party, taking a nap on the patio or swimming in the pool. Come experience a truly relaxing vacation disconnecting from the “busyness” of life and connecting with those that matter 🤍

Guest favorite

A lush green lawn is seen in front of the villa, framed by tropical plants and flowering shrubs. The outdoor space includes a patio area with tables and chairs, along with a pool that invites relaxation. The vibrant colors of the surroundings create a refreshing atmosphere.

Apartment in Bon Accord

4.88 out of 5 average rating, 161 reviews

1st floor private apartment

Welcome to Palm Breeze Villa — ideal for couples and small families. A tropical escape on the edge of Crown Point. Just a short stroll away are two of Tobago’s most stunning beaches: Pigeon Point and Store Bay. Spend your days soaking up the sun, swimming in crystal-clear waters, and your evenings enjoying breathtaking sunsets at Store Bay. We’re also within a 5-minute walk to grocery stores and a strip of restaurants and bars, making it easy to enjoy the best of local flavor and nightlife.

Superhost

A refreshing swimming pool features a semi-circular shape with blue mosaic tiles and steps leading into the water. Sun loungers in vibrant red are arranged on the patio, while a spacious villa with shaded doorways and windows is visible in the background, surrounded by greenery.

Home in Canaan

4.89 out of 5 average rating, 87 reviews

Samsara Villa - a cool and cosy home

Samsara Villa is a cool and breezy, three-bedroom property located in the much sought-after Samaan Grove gated community in Canaan, Tobago. Each of the three bedrooms is air conditioned, and they also have ceiling fans and an en-suite bathroom. The master bedroom has two queen size beds and can sleep four persons; the other two bedrooms have one queen size bed accommodating two persons each. The living room and dining room area is open plan and leads out onto a wide back porch and garden area.

Top guest favorite

An infinity pool reflects the sky, surrounded by a wooden deck and tropical foliage. Sun loungers under large umbrellas are positioned nearby. The villa structure features elegant overhangs, promoting natural light and providing shaded areas for relaxation.

Apartment in Bethel

4.99 out of 5 average rating, 136 reviews

Firefly Villa - 'Roots'

A spacious, modern, beautifully decorated home with a zen vibe and an inspiring location for working away from home. ‘Roots’ has two cozy double bedrooms, comfortable work spaces and fully-equipped kitchen with kitchen island, and deluxe double fronted fridge, en-suite bathrooms and wooden floors. Lie by the infinity pool and watch as a bright blue-grey tanager flies right over your head from one tree to the next. The perfect blend of treehouse and charming, stylish Caribbean poolside villa.

Superhost

A spacious outdoor gazebo is featured, complete with a comfortable seating area and an outdoor television. The design allows for easy access to the inviting heart-shaped pool, which is surrounded by lush greenery, enhancing the relaxing atmosphere of the property.

Villa in Canaan

4.88 out of 5 average rating, 40 reviews

Heart Villa:5BR FamilyRetreat,Sleeps15,Pool,Garden

The Heart Villa in Samaan Grove, a tropical paradise with a unique heart-shaped pool ideal for groups and family gatherings. Located near all the beautiful beaches. This 5 Bedroom villa combines luxury with tropical elegance, featuring an open-plan indoor and outdoor living areas that open to a stunning pool, offering Caribbean views and breeze. Equipt rooms with en-suite baths and air conditioning. Enjoy a large gazebo with outdoor TV & BBQ area, and full amenities for a comfortable stay.

Superhost

A spacious villa is showcased with a private swimming pool in the foreground. The building features a modern design with large windows, and comfortable lounge chairs are visible on the patio. Surrounding greenery enhances the inviting outdoor environment.

Villa in Canaan

4.86 out of 5 average rating, 35 reviews

Villa Mila #35

This property is located in Samaan Grove, Golden Grove, Canaan, Tobago. A secure gated community which consists of a large number of high-end villas, used for both personal and rental purposes. As you enter the development, it possesses a relaxing ambiance surrounded by lakes, trees and stunning landscaped gardens throughout. This beautiful villa has a private swimming pool with a patio. This area is a perfect area for liming with family/friends or just relaxing with a glass of wine.

Guest favorite

The outdoor area features a private pool surrounded by a spacious deck. Two lounge chairs are positioned beside the pool, while the house's exterior showcases large windows and a modern roof design. Lush greenery is visible in the background, adding to the tranquil environment.

Home in Bon Accord

4.92 out of 5 average rating, 118 reviews

The House of Serenity, Play & Family

This place is perfect for a small or relatively large group. It is equipped with a fully-functional modern-styled kitchen, a spacious communal area, a family-friendly pool and beautiful garden. The place is situated in a secured gated community in lively Crown Point! We are also located close to the airport (5 mins drive), beaches (e.g. Pigeon Point - the #1 attraction in Tobago!), restaurants, bars, shops, grocery stores and ATMs (bank) for all your needs and amenities.

Guest favorite

A serene swimming pool is framed by a smooth patio, where several loungers invite relaxation. Lush greenery surrounds the area, enhancing the peaceful atmosphere of the outdoor space.

Home in Canaan

4.91 out of 5 average rating, 23 reviews

Sea Glass Villa Tobago-sleeps 12

This is a very beautiful and private Villa, the beds are super comfy, all bedrooms are ensuite and the Kitchen is fully equipped, it is truly a home away from home The Villa sleeps a max of 12 persons including kids, the price is based on Occupancy, please book for the correct number of persons to get the exact cost. The base price is on 4 persons, every person thereafter is $15 per person per night, this is structured so that smaller groups do not pay the full price.

Top guest favorite

A spacious living area is characterized by modern furnishings, featuring a navy blue sectional sofa with decorative pillows. A coffee table sits atop a woven area rug, and natural light floods the space through ceiling windows, illuminating the open layout that connects to the kitchen.

Villa in Crown Point

4.96 out of 5 average rating, 56 reviews

Villa Blue Moon

Make memories at this unique and family-friendly place. A 4 bedroom 10 person villa located in secured compound close to beaches, bars and restaurants. With fun activities such as pool table, basketball, heated jacuzzi, swimming pool, 3 televisions, modern fully equipped kitchen, laundry room with washer & dryer, comfortable family room and Hi-Fi stereo system. A playful, open and entertaining home to feed your senses, to enjoy and unwind as you will

Guest favorite

A sparkling blue swimming pool is complemented by a relaxing jacuzzi. The pool area is surrounded by well-maintained landscaping and features elegant arch-shaped windows of a nearby building, creating a serene and inviting outdoor space.

Apartment in Western Tobago

4.87 out of 5 average rating, 93 reviews

Paradise Place Apartments. Close to everything!

Spacious, modern, elegantly decorated apartment close to everything & away from the noise! Surrounded by views of the hillside, the apartment is equipped with queen sized bed, sofa in the living room, smart tv, large bathroom with massage shower, fully equipped kitchen, balcony, hot water, wifi, swimming pool and jacuzzi. Ideal for a couple looking for relaxation. Close access to beaches and night life. Apartment is located in a safe community.

Superhost

A spacious outdoor area features a clear blue pool surrounded by lounge chairs. Lush greenery and colorful plants enrich the environment, while a well-designed villa stands in the background. The sun-drenched atmosphere highlights the inviting design and layout of the space.

Villa in Bon Accord

4.7 out of 5 average rating, 33 reviews

Luxury villa, pool and the best botanical garden!

Only 300m or yds from the sparkling Caribbean Sea in the Bon Accord district lies this exquisite, luxury 3-bedroom villa. Villa de Lena is specially designed to capture the warmth and comfort of Tropical Tobago. It facilitates walking distance to the Crown Point area which houses two of Tobago's finest beaches, Pigeon Point and Store Bay. Glass bottom boats to the famous Buccoo Coral Reef leave from here.

Top guest favorite

A private pool is surrounded by well-maintained greenery and decorative planters. The pool features a smooth edge with stairs leading into the water, and the bright blue surface reflects the sky above. A storage tank is positioned discreetly in the background.

Home in Bon Accord

4.97 out of 5 average rating, 119 reviews

Villa Magnolia

This cozy duplex is located just walking distance from both the airport and the world famous Pigeon Point beach. You can also enjoy several varieties of food just minutes away from this villa. Guests are sure to enjoy a memorable vacation in this fully furnished, cozy 3 bedroom villa, each with its individual bathroom with a powder room located on the main floor. The villa also includes a private pool.