Vacation 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 favorite

Villa in Canaan

4.94 out of 5 average rating, 33 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 🤍

Superhost

Villa in Lowlands

4.82 out of 5 average rating, 83 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)

Superhost

Villa in Tobago

4.79 out of 5 average rating, 97 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 favorite

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.

Guest favorite

Villa in Union

4.97 out of 5 average rating, 35 reviews

The Forest View at Robyn’s Nest

This stylish studio is designed for the utmost comfort of two guests, featuring contemporary furnishings and amenities. The highlight of the space is undoubtedly the view that seamlessly merges the indoors with the beauty of nature. Inside, you'll find a fully equipped kitchenette and a sleek bathroom for your convenience. Step into the shared pool or outside onto the open deck to bask in the gentle breeze and panoramic vistas, accompanied by the melodic tunes of the local birdsong.

Guest favorite

Home in Bon Accord

4.91 out of 5 average rating, 117 reviews

La Casa de Serenidad, Juego & Familia

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 favorite

Cottage in Lowlands

5 out of 5 average rating, 23 reviews

Beautiful 2-bedroom cottage with pool

Villa Laguna: a beautiful , comfortable and serene cottage… Unwind in this little piece of paradise. Paddle in the Petit Trou Lagoon and take in its wide variety of flora and fauna. Laguna’s kayaks are at your doorstep (1 double and 1 single.) Tobago is an an ideal location for bird watching, several of which can be seen within Tobago Plantations and right from your deck. Or take in its exquisite sunsets with a sundowner, or while finishing a round of golf.

Guest favorite

Villa in Plymouth

4.95 out of 5 average rating, 19 reviews

Top O Tobago Villa & Cabanas: Main House

Sleeping 6, the main house at Top O’ Tobago is ideal for a small family. It is the largest of the accommodations on the property which also includes 3 cabanas. Its sole position on the hilltop gives 360 degree views. You can walk to Arnos Vale Beach, one of the island’s best snorkeling beaches, and it is a 25 min. drive to the airport and the many tourist activities on Tobago’s south. Silja, our manager, lives onsite. You’ll love the inside/outside living.

Superhost

Villa in Bon Accord

4.7 out of 5 average rating, 33 reviews

Luxury villa, pool and the best botanical garden!

Only 300m or yds from the sparkling Caribbean Sea in the Bon Accord district lies this exquisite, luxury 3-bedroom villa. Villa de Lena is specially designed to capture the warmth and comfort of Tropical Tobago. It facilitates walking distance to the Crown Point area which houses two of Tobago's finest beaches, Pigeon Point and Store Bay. Glass bottom boats to the famous Buccoo Coral Reef leave from here.

Top guest favorite

Home in Bon Accord

4.97 out of 5 average rating, 119 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 favorite

Apartment in Black Rock

4.97 out of 5 average rating, 35 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 favorite

Cabin in Parlatuvier

4.94 out of 5 average rating, 114 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.