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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
The exterior of the villa is presented, featuring a sloped roof and vibrant orange window frames. A green wooden fence encloses the property, complemented by neatly trimmed hedges and a manicured lawn, which adds to the welcoming ambiance of the gated community.
Villa in Canaan
4.95 out of 5 average rating, 38 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 🤍

Top guest favorite
Apartment in Crown Point
5 out of 5 average rating, 33 reviews

Citrine-Dreamy mall studio unit

This unique place has a style all its own. If you’ve ever wanted to be at the heart of it all, yet in your own dreamy getaway, this stylish modern studio apartment unit is just right for you. Located on the top floor of the distinct architecture of the D’ Colluseum Mall in Crown Point, Tobago, this unit has access to the most renowned beaches of Pigeon Point and Store bay beach facilities and its own in-house gym, to maintain that toned figure. Want to create a chill mood? Just ask Alexa.😉

Superhost
An aerial view captures the villa's layout, featuring a heart-shaped pool surrounded by patio space. Lush greenery borders the property, highlighting the expansive lawn. A paved driveway leads to the entrance, while a gazebo with seating is visible near the pool area.
Villa in Canaan
4.87 out of 5 average rating, 47 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.

Top guest favorite
A wrap-around balcony offers panoramic views of the sunset over lush tropical trees and the Caribbean Sea. Floor-to-ceiling glass doors line one side, inviting natural light and providing easy access to the outdoor space.
Apartment in Bethel
4.97 out of 5 average rating, 178 reviews

Firefly Villa - 'Treetop'

Combining luxury and comfort, is any holidaymakers dream, romantic getaway for couples or an ideal space for working away from home. Open-plan floor to ceiling sliding glass doors that open out onto a wrap-around balcony, elevates outdoor living to a whole new level. Admire the stunning views of the Caribbean Sea and Buccoo reef or look down at the treetop canopy and watch the exotic tropical birds fly by. Peaceful, relaxed and inspiring. Contemporary comfort - timeless Caribbean charm.

Top guest favorite
Apartment in Crown Point
5 out of 5 average rating, 5 reviews

Beach Retreat: Central Crown Point Condo

Location, location, location! No need for a car in this secure 1 bedroom condo based in the heart of Crown Point. Enjoy quick and easy access on foot to countless restaurants and take-out options, shops, ATMs, nightlife and South West Tobago’s most beautiful and popular beaches. Equipped with a full kitchen, shared pool, washer/dryer, 50 inch Smart TV, queen sized bed, pull out twin day bed and A/C throughout. Come “retreat” from the beach at this cozy condo in the heart of Crown Point!

Top guest favorite
The hallway showcases a wooden sign reading 'IVB Buccoo Place' on a white wall. A sliding barn door is positioned to the right, leading to a living area. Neutral-toned flooring extends throughout, leading to a cozy seating arrangement with cushions in warm colors visible in the distance.
Apartment in Buccoo
4.97 out of 5 average rating, 58 reviews

Guest Favourite - The Balcony, 4B Buccoo, 2BR Apt

Explore our stylish condo in Buccoo, with onsite restaurants and a coffee shop, just 7 minutes drive from Buccoo Bay, 10 minutes from Grafton and Mt Irvine beaches and Golf Course. Approx 15 minutes from Pigeon Pt and Store Bay beaches. Experience modern comfort, strategically placed for effortless exploration of Tobago's treasures; Nylon Pool, Argyle Waterfall, scenic drive through the rain forest to list a few. Sea Horse, Waves and Fish Pot restaurants all within 10 mins drive.

Guest favorite
Two comfortable chairs are positioned on a tile patio, overlooking a scenic ocean view. Lush greenery surrounds the area, and a vibrant blue sky with scattered clouds enhances the relaxing atmosphere. The infinity pool is visible, seamlessly blending with the horizon.
Home in Golden Grove
5 out of 5 average rating, 10 reviews

Oceanview Villa w/ Infinity Pool

Enjoy a relaxing escape at our oceanview villa. Nestled in a gated community, this serene retreat features magnificent ocean views and an infinity edge pool. The villa comfortably sleeps 6, with 3 spacious bedrooms and 3 full bathrooms, providing plenty of room to unwind. With private parking and the security of a gated setting, it’s perfect for families, friends, or couples seeking comfort and stunning views. Make your stay memorable in this well-appointed home away from home.

Guest favorite
A communal living area features a spacious sectional sofa arranged around a central ottoman. Natural light fills the room through large windows, showcasing the modern kitchen in the background with wood cabinetry and high chairs at the island.
Home in Bon Accord
4.9 out of 5 average rating, 125 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
4.92 out of 5 average rating, 25 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.

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
4.97 out of 5 average rating, 59 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

Top guest favorite
A dining area is shown with a wooden table surrounded by four gray chairs. A simple centerpiece and placemats are placed on the table. A circular mirror and a framed artwork are mounted on the wall. A small shelf with potted plants is visible in the background.
Apartment in Buccoo
5 out of 5 average rating, 20 reviews

Island breeze penthouse

Forget your worries in this elegant, beautiful and relaxing space. Our penthouse is located at Building 9, Apartment 4D. Sip your coffee in our balcony while enjoying the morning island breeze and a view of the pool. You will find delicious doubles just in front of the compound and the best chicken sandwich from Block 22. Enjoy both pools, one in the morning and the other in the evening. There is a gym, one minute away, next to to the food court.

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
4.98 out of 5 average rating, 123 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.

Popular amenities for Canaan rentals with a pool

When is the best time to visit Canaan?

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Avg. price$325$194$195$197$198$203$260$260$243$300$295$313
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Quick stats about vacation rentals with a pool in Canaan

  • Total vacation rentals

    Explore 50 vacation rentals in Canaan

  • Nightly prices starting at

    Canaan vacation rentals start at $60 per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Canaan vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Canaan rentals

  • 4.8 Average rating

    Canaan stays are highly rated by guests—averaging 4.8 out of 5!