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Holiday 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 favourite
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 favourite
A cozy living area features a comfortable blue sofa and a white media unit with a television. Large windows are dressed with light curtains, allowing natural light to brighten the space. A decorative plant is positioned on a table, adding a touch of greenery.
Condo in Tobago
5 out of 5 average rating, 29 reviews

Sapphire-Vibrant & Relaxing 3mins to Buccoo Beach

Conveniently located. Just kick back and relax in this calm, stylish condo. Just 5 mins to Buccoo beach, this fully equipped unit is tucked away but easily accessible to all the going ons of our charming island. Whatever your in the mood for from kayaking, goat racing, horse back riding to partying at the popular Sunday school spot on the weekend. If you just want to relax and unwind, our evening poolside light show helps rejuvenate your senses with color therapy while you gaze at the stars.

Guest favourite
The exterior of a two-story villa is surrounded by lush tropical vegetation and manicured lawn. A wide balcony with decorative railings offers a view of the garden. A paved walkway leads to the front entrance, with a teardrop pool visible nearby.
Apartment in Bon Accord
4.88 out of 5 average rating, 165 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.

Guest favourite
Home in Canaan
4.89 out of 5 average rating, 88 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 favourite
An infinity pool glistens under a bright blue sky, with clouds casting soft shadows. Comfortable lounge chairs with umbrellas line the poolside, surrounded by lush greenery. The structure of the villa features large windows and a wooden overhang, blending seamlessly with the natural environment.
Apartment in Bethel
4.99 out of 5 average rating, 137 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.

Guest favourite
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.

Guest favourite
Apartment in Crown Point
5 out of 5 average rating, 6 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!

Guest favourite
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 favourite
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, 126 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 favourite
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.

Top Guest favourite
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 favourite
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.

Popular amenities for Canaan rentals with a pool

When is the best time to visit Canaan?

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Avg. price$489 AUD$292 AUD$293 AUD$296 AUD$298 AUD$305 AUD$391 AUD$391 AUD$365 AUD$451 AUD$444 AUD$471 AUD
Avg. temp27°C27°C27°C28°C29°C28°C28°C28°C29°C28°C28°C27°C

Quick stats about holiday rentals with a pool in Canaan

  • Total holiday rentals

    Explore 50 holiday rentals in Canaan

  • Nightly prices starting at

    Canaan holiday rentals start at $90 AUD per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Canaan holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Canaan rentals

  • 4.8 Average rating

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