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Holiday rentals with a pool in Western Tobago

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Western Tobago

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A comfortable living area features two gray sofas adorned with patterned throw pillows, positioned across from a light wooden coffee table. A decorative vase sits on the table, and a subtle area rug completes the space. A door and artwork are visible in the background.
Guesthouse in Scarborough
5 out of 5 average rating, 5 reviews

Carlton’s Haven at Robyn’s Nest

Carlton’s Haven at Robyn’s Nest Tucked away in the tranquil village of Union, Tobago, Carlton’s Haven is a modern two bedroom, two bath, condo style duplex designed to make you feel completely at ease. Surrounded by lush greenery, the soothing sounds of birds, and cool island breezes, it’s your perfect escape into nature while still enjoying contemporary comfort and style. A 5-minute drive from Scarborough our capital putting local markets, beaches, and cultural gems right at your fingertips.

Superhost
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
4.82 out of 5 average rating, 84 reviews

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)

Top Guest favourite
A lush garden is seen with vibrant banana plants and a variety of trees, leading to a serene outdoor area. A calm pathway guides the view down to a swimming pool, while colorful seating options invite relaxation amidst the greenery, with the ocean visible in the background.
Home in Scarborough
5 out of 5 average rating, 62 reviews

BACOLET BLISS

Perfectly nestled amongst the trees, with just a few short steps to reach the warm and inviting Atlantic ocean, a slice of paradise awaits you. Come to our hidden 3+ bedroom escape! Lose yourself within the lush greenery and the cool waves of the ocean. There's a taste of everything natural here, from the sweet sounding birdsong at the first rays of dawn that lingers beyond the last wisps of twilight, to the remarkable sunrises and luminous star studded nights. Welcome to a great vacation!

Superhost
The villa exterior is showcased under a starry night sky, with a tranquil saltwater pool reflecting the lights of the structure. Surrounding lounge chairs are arranged by the poolside, and vibrant wall art adds character to the setting.
Villa in Tobago
4.79 out of 5 average rating, 99 reviews

Nirvana Tobago Villa Saltwater Pool & Ocean View

Nirvana Tobago is a luxurious Private Villa on the Caribbean coast with Ocean Views. Ample alfresco dining space, poolside cabana bar and saltwater pool. Over 4000+ sq. ft residence is graced with 12-foot ceilings and skylights. Interiors feature a chef kitchen and well-appointed bedrooms with ensuite bathrooms, no better place to restore your sense of bliss! Perfect for weekend getaways, extended stays and remote working. We have fast and reliable wifi and laptop friendly workspaces.

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.
Apartment 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.

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.
Apartment in Buccoo
4.96 out of 5 average rating, 57 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, 124 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 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, 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.
Apartment 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.

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, 121 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.

Guest favourite
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
4.97 out of 5 average rating, 37 reviews

Sunset on the ocean

This apartment is unique in the Tobago short term rental space. Brand new, stylish "island chic" place offers ocean views and is right above one of the most stunning Tobago beaches. You have ample space for your family or as friends to enjoy spacious living and dining space, top of the art kitchen. The two bedrooms and 2.5 bathrooms give you the space to enjoy this calm yet very well located new spot.

Guest favourite
The covered porch area features wooden lounge chairs, inviting relaxation. A backdrop of lush greenery and the tranquil bay is visible beyond the railing, where palm trees sway gently. The patio flooring is wooden, enhancing the natural ambiance.
Cabin in Parlatuvier
4.93 out of 5 average rating, 118 reviews

Tamarind House Villa Parlatuvier

Tamarind House Villa is situated on the leeward coast of Tobago in the beautiful fishing village of Parlatuvier. It is suitable for small groups, couples and families who enjoy a relaxed lifestyle away from commercial tourist areas. The villa overlooks the bay on one side and pristine tropical rainforest on the other. Guests will have sole occupancy of the house, pool and gardens.

Popular amenities for Western Tobago rentals with a pool