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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, 39 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, 170 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
The two-story villa features a warm orange exterior with arched balconies and a tiled roof. A freeform pool is visible in the foreground, accompanied by a spa. Several sun loungers are positioned around the pool, while lush greenery frames the property.
Home in Bon Accord
4.74 out of 5 average rating, 105 reviews

Casa Bon - a charming Bon Accord home

Casa Bon offers all the comforts you need in a Caribbean holiday home! It is conveniently located in the Bon Accord area and is walking distance to Store Bay and Pigeon Point - two of Tobago's most popular beaches. This charming Spanish-style villa is set in lush, tropical gardens and has four air conditioned bedrooms, three of which have ensuite bathrooms. The open plan living and dining rooms flow right onto the patio and pool deck complete with a free form swimming pool and attached spa.

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
4.88 out of 5 average rating, 56 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, 181 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
4.88 out of 5 average rating, 42 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 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
4.89 out of 5 average rating, 132 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.

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, 69 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 favourite
A private villa showcases a serene pool area with multiple lounge chairs arranged around it. Soft evening light highlights the modern architectural features and the inviting entrance, while palm trees stand in the background, enhancing the peaceful ambiance of the space.
Home in Canaan
4.92 out of 5 average rating, 26 reviews

Flamingo Villa Tobago-sleeps 14

Experience the epitome of elegance and luxury in this stunning 4-bedroom villa, nestled within a serene and secure gated community. Ideally located just moments from the airport and pristine, sun-kissed beaches, this exquisite retreat offers the perfect blend of sophistication, comfort, and convenience. For larger groups, the adjacent Sea Glass Villa—accessible via a private gated entrance—offers an exceptional opportunity to expand your accommodations.

Top guest favourite
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, 127 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 warm and private salt water pool.

Superhost
The villa features a charming exterior with a triangular roof and a prominent yellow door. Surrounding landscaping includes lush greenery and colorful plants, complementing the light gray facade. The brick driveway adds an inviting touch to the entrance.
Villa in Canaan
4.88 out of 5 average rating, 17 reviews

Villa Oceana - Luxury Holiday Villa

Villa Oceana is a luxurious and spacious holiday villa in the popular gated community of Samaan Grove. Located in the southwest of the island, Samaan Grove is close to both the activity of Crown Point with its restaurants, nightlife and the world-famous Pigeon Point beach as well as being a stone's throw from the Mt. Irvine Golf Course and the beautiful beaches at Mt. Irvine Bay and Grafton.

Superhost
Apartment in Golden Grove
5 out of 5 average rating, 4 reviews

Diamond-ADA Friendly, 5-8mins to beach/airport

This newly renovated unit is perfect for extended family stay or small group trips. Its ambience both inside and outside, provides a convenient and accessible access to family inclusion and bonding time without sacrificing safety or ambience. Ideally located near to the conveniences of the Buccoo and Mount Irvin beach facilities, Shirvan plaza and Shirvan police station.

Popular amenities for Canaan rentals with a pool

When is the best time to visit Canaan?

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Avg. price$417 SGD$249 SGD$250 SGD$253 SGD$254 SGD$260 SGD$333 SGD$333 SGD$312 SGD$340 SGD$254 SGD$256 SGD
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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 $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 710 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!