Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
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
4.94 out of 5 average rating, 35 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 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.
Flat in Bon Accord
4.88 out of 5 average rating, 162 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
The exterior of the villa features a charming façade with a sloped roof and decorative gables. A swimming pool with a spa area is situated to the front, surrounded by loungers. Large doors provide access to the interior, complemented by a sunlit patio area.
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.

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, 45 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 favourite
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.
Flat in Bethel
4.97 out of 5 average rating, 177 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.

Guest favourite
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
4.87 out of 5 average rating, 38 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.

Top guest favourite
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.
Flat in Buccoo
4.96 out of 5 average rating, 55 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 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, 123 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.

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
4.96 out of 5 average rating, 57 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.
Flat in Buccoo
5 out of 5 average rating, 16 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 favourite
A modern dining area features a wooden table surrounded by six light-colored chairs. A decorative plant sits at the center of the table. A large framed image of a turtle swimming above coral decorates the wall, adding a coastal touch to the space.
Flat in Buccoo
5 out of 5 average rating, 12 reviews

Buccoolito 2B - Modern Condo w/Pool | Near beach

Comfort, convenience, and island charm await at Buccoolito 2B Enjoy this 2-bedroom, 2-bathroom modern condo with a fully equipped kitchen and a perfect view of the pool. Located in a secure, gated development with 24/7 security, Buccoolito 2B is just 15 minutes from both the airport and the ferry terminal. Centrally located, minutes away from the Picturesque Buccoo Beach and 15 minutes drive to the Popular Pigeon Point Beach and Store Bay Beach.

Popular amenities for Canaan rentals with a pool

When is the best time to visit Canaan?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£245£146£147£148£149£153£236£241£218£221£222£236
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 £45 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 & child-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Canaan holiday rentals include wifi 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!