Holiday rentals with a pool in Canaan

4.94 out of 5 average rating, 48 reviews

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, Tobago

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 🤍

LocationFamilyKitchen

5.0 out of 5 average rating, 28 reviews

Condo in Buccoo

Buccoo Luxe Escape|3BR Condo w/Pool & Modern Charm

Welcome to Aurelia - a radiant escape where tropical serenity meets quiet luxury. Featuring warm natural finishes with sleek contemporary lines, Aurelia invites you to slow down and reconnect in refined comfort. This newly furnished 3-bedroom condo is artfully designed for families, friend groups, or long-stay guests seeking a luxurious escape close to beaches and island attractions. Relax in the open-plan living area with comfortable lounge seating and doors that open to your private balcony.

LocationValueDecor

4.75 out of 5 average rating, 110 reviews

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

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.

LocationFamilyBathroom

4.84 out of 5 average rating, 101 reviews

The exterior of a modern villa is displayed, featuring a spacious upper balcony with white railings above large glass doors. Lush greenery surrounds the property, and a private pool is visible on the lower level, creating a serene outdoor atmosphere.

Villa in Lowlands

Sea View Villa Cluster 63A(2BR,Pool,Wifi,Golf)

Sea front villa with scenic entrance near the Magdalena Hotel with an international Golf Course. Minutes away from iconic beaches and shopping malls. Furnished, 2 bedrooms with upgraded ensuite bathrooms, open concept, and a private pool with sundeck on the ground floor of the duplex. Gated community(manned 24 hours) Fully air-conditioned along with ceiling fans & Netflix. Contains outside bathroom and utility room. * Maid service available at an additional charge.(Mandatory after 3nights)

LocationValueNearby

4.81 out of 5 average rating, 74 reviews

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, Tobago

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.

FamilyValueBathroom

4.97 out of 5 average rating, 183 reviews

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

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.

ValueFamilySleep quality

4.88 out of 5 average rating, 49 reviews

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

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.

LocationFamilyKitchen

4.94 out of 5 average rating, 31 reviews

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

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.

FamilyLocationNearby

4.98 out of 5 average rating, 86 reviews

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

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

LocationValueHot tub

4.96 out of 5 average rating, 136 reviews

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

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.

FamilyLocationCheck-in

5.0 out of 5 average rating, 17 reviews

Condo in Golden Grove

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.

FamilyLocationCheck-in

4.88 out of 5 average rating, 16 reviews

The house is showcased with a modern design, featuring a light blue exterior and a grey roof. A vehicle is parked in front, while a well-manicured lawn with green grass enhances the inviting entrance. Large windows create a bright and open appearance.

Home in Canaan

Villa Delphinae

Welcome to your dream vacation getaway in Samaan Grove, Canaan, Tobago. This exquisite 4-bedroom 4.5 bathroom vacation house, is a perfect blend of tropical serenity, modern comforts, and easy access to the island's most captivating attractions. It promises an unforgettable retreat for families and groups seeking a slice of Caribbean paradise.

FamilyValueCondition

Popular amenities for Canaan rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5.0 out of 5 average rating, 3 reviews

A luxurious outdoor space features a serene swimming pool surrounded by sun loungers and umbrella-covered seating areas. A shaded gazebo offers additional relaxation, while a small table is set for beverages, creating an inviting atmosphere for leisure.

Home in Canaan

Bella Sienna in Samaan Grove

CleanlinessComfortCondition

5.0 out of 5 average rating, 19 reviews

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

Oceanview Villa w/ Infinity Pool

LocationFamilyKitchen

5.0 out of 5 average rating, 16 reviews

Home in Lowlands

New 5-BR Villa Pool • Cine • Gym • Beach • Private

FamilyLocationCleanliness

4.92 out of 5 average rating, 74 reviews

The exterior of the villa features a two-story structure with a balcony and large glass doors. A serene pool is situated in the foreground, surrounded by well-maintained greenery and potted plants, providing a refreshing atmosphere.

Home in Crown Point

Suncoast Villa

ValueLocationAmenities

4.75 out of 5 average rating, 20 reviews

Home in Lambeau

Oceanview Townhouse · 4 Ensuites + Plunge Pool

FamilyLocationGetting around

4.56 out of 5 average rating, 18 reviews

Home in Lowlands

Casa Verde Villa, Tobago Plantations

FamilyLocationBarbecue

4.92 out of 5 average rating, 26 reviews

A vibrant sunset paints the sky with shades of orange and purple above a lush green landscape. The view encompasses the distant ocean and various trees, with a spacious villa and neighboring structures positioned in the foreground.

Home in Plymouth

Plymouth View Villa: 2br & Pool

LocationFamilyHospitality

Home in Lowlands

New place to stay

Silver Button

Condo rentals with a pool

4.85 out of 5 average rating, 89 reviews

A shared pool is framed by a stone patio, reflecting the nearby condominium. Lush greenery and ornamental plants enhance the surroundings. The modern two-level building in the background features multiple balconies and large windows, allowing for natural light to illuminate the interior spaces.

Condo in Buccoo

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

ValueFamilyComfort

4.78 out of 5 average rating, 92 reviews

The two-story villa features a spacious terrace with a private plunge pool surrounded by tropical greenery. A dining table and chairs are positioned on the terrace, offering a place for outdoor relaxation. The well-maintained exterior includes large windows and a barbecue area.

Condo in Lowlands

Austin Tobago Retreat - Villa 41A (Lower Level)

ValueFamilyCheckout

4.97 out of 5 average rating, 29 reviews

Condo in Black Rock

Mahi Mahi Suite, A Seaside Retreat that Sleeps Six

LocationValuePool

4.91 out of 5 average rating, 11 reviews

The inviting swimming pool reflects the colors of the sunset, surrounded by a spacious patio. A covered seating area is visible in the background, with palm trees framing the scene. The calm water enhances the tranquil ambiance of the hotel grounds.

Condo in Crown Point

Romantic One Bedroom Apartment right on the beach

LocationFamilyComfort

5.0 out of 5 average rating, 5 reviews

The exterior of the property features a modern triangular roofline with a mix of light-colored stone and painted walls. Large windows are situated symmetrically along the front, showcasing a balanced architectural design. A spacious entrance is highlighted by a stone accent wall.

Condo in Lowlands

Lovely 6 Bedroom Villa Saltwater Pool 24 Guests

LocationFamilyCheck-in

5.0 out of 5 average rating, 25 reviews

Condo in Buccoo

Buccoo Escape - 2 bedroom cozy condo near beach

FamilyLocationPool

Condo in Mount Saint George

A lush hillside is depicted, featuring tropical vegetation and palm trees along the coastline. The vibrant orange building sits atop the hill, overlooking the clear blue water. A wooden walkway meanders along the shore, providing access to the rocky edge of the ocean.

4.94 out of 5 average rating, 84 reviews

The Oasis w/ private beach & great view #432211004

LocationValueLayout

The tropical complex features a three-story structure with multiple balconies overlooking a serene pool area. Lush greenery and palm trees surround the property, creating a peaceful ambiance. Lounge chairs are positioned by the pool, inviting relaxation under the clear blue sky.

Condo in Black Rock

4.81 out of 5 average rating, 31 reviews

Hibiscus Suite at Black Rock Dreams

FamilyLocationDecor

Other holiday rentals with a pool

4.89 out of 5 average rating, 9 reviews

The modern villa features large glass windows and a spacious deck. An inviting outdoor pool is bordered by lounge chairs and shaded by a large umbrella, providing a perfect spot for relaxation. Lush greenery surrounds the property, enhancing the serene atmosphere.

Villa in Canaan, Tobago

Poui Place - 4 Bd villa in Samaan Grove, Tobago

LocationFamilyPool

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.

5.0 out of 5 average rating, 39 reviews

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

FamilyLocationAccuracy

4.95 out of 5 average rating, 57 reviews

A bright living and dining area is featured, with large windows allowing natural light to fill the space. A comfortable gray sectional couch and a light-colored coffee table are positioned in front of a television. A dining table with chairs and artwork on the wall add to the inviting ambience.

Apartment in Black Rock

Sunset on the ocean

FamilyLocationNearby

4.7 out of 5 average rating, 47 reviews

Townhouse in Bon Accord

Roof Top Hideaway

LocationFamilyCheck-in

5.0 out of 5 average rating, 47 reviews

Island breeze penthouse

LocationValuePool

4.96 out of 5 average rating, 90 reviews

Guest Favourite - El Balcón, 4B Buccoo, 2BR Apt.

FamilyLocationBathroom

4.8 out of 5 average rating, 111 reviews

Villa

Nirvana Tobago Villa Saltwater Pool & Ocean View

ValueLocationAccuracy

A private balcony is furnished with two dark wicker chairs, overlooking a green landscape. A view of a serene yard, featuring manicured grass and palm trees, is presented. In the distance, a white vehicle is parked along the lane, complementing the peaceful surroundings.