Vacation rentals with a pool in Tobago

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Tobago

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

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Guest favorite

A clear blue pool is surrounded by a terracotta patio, with comfortable lounge chairs arranged nearby. Lush greenery is visible in the background, alongside a view of the ocean under a clear sky. The area offers a spacious and relaxing environment.

Apartment in Plymouth

4.91 out of 5 average rating, 86 reviews

Cabanas 3 with Private Gazebo; Walk to Beach

Cabana 3 at Top O’Tobago is ideal for a couple on a romantic getaway, a young family, or a group of 4 singles on a weekend adventure. It is a studio apartment with a dining gazebo and garden. It is the lowest of our 3 cabanas with level access to parking and steps away from the swimming pool. 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.

Top guest favorite

An infinity pool reflects the sky, surrounded by a wooden deck and tropical foliage. Sun loungers under large umbrellas are positioned nearby. The villa structure features elegant overhangs, promoting natural light and providing shaded areas for relaxation.

Apartment in Bethel

4.99 out of 5 average rating, 124 reviews

Firefly Villa - 'Roots'

A spacious, modern, beautifully decorated home with a zen vibe and an inspiring location for working away from home. ‘Roots’ has two cozy double bedrooms, comfortable work spaces and fully-equipped kitchen with kitchen island, and deluxe double fronted fridge, en-suite bathrooms and wooden floors. Lie by the infinity pool and watch as a bright blue-grey tanager flies right over your head from one tree to the next. The perfect blend of treehouse and charming, stylish Caribbean poolside villa.

Guest favorite

Villa in Lowlands

4.91 out of 5 average rating, 43 reviews

Villa Yemanjá

Named after the Brazilian goddess of the sea, Yemanjá is a luxurious oceanfront villa located in the prestigious Tobago Plantations Estate. The colonial style architecture of the villa is enhanced by a lush landscaped tropical garden. Balinese inspired decor soothes the senses. The property features four en-suite bedrooms, a double bed loft and a maid’s quarters, comfortably sleeping 11. A spaciously covered patio opens out onto an infinity swimming pool, heated Jacuzzi and pebble beach.

Guest favorite

Apartment in Western Tobago

4.81 out of 5 average rating, 75 reviews

Pool View Apartment. Close to everything!!!

Be COVID Free! Have a fear of contracting COVID whilst on vacation?Then this is the correct accommodation for you! Spacious, modern, elegantly decorated studio. Close to all major sites and attractions but away from overly crowded spaces. Apartment is equipped with a queen sized bed, sofa, smart tv, large bathroom, fully equipped kitchen, hot water, wifi, swimming pool and much more! Ideal for short or long term stays and for couples looking for time away. Come enjoy relaxation in style.

Guest favorite

A contemporary villa exterior is showcased, featuring a saltwater pool bordered by lounge chairs. The poolside cabana bar is visible in the background, framed by lush greenery and a clear blue sky.

Villa in Tobago

4.86 out of 5 average rating, 88 reviews

Nirvana Luxury 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 6000+ 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.

Superhost

A shaded pool area features a spacious in-ground pool with calm blue waters, accented by a rock feature. Two lounge chairs are positioned beside the pool, while panoramic sea views and lush greenery surround the space, creating a serene outdoor environment.

Home in Castara

4.81 out of 5 average rating, 26 reviews

The Wood House

The Wood House is a beautiful, secluded, open-plan cottage with spectacular sea views, a natural setting in a reclaimed woodland, and close proximity to Englishman’s Bay (considered one of the 10 most beautiful beaches in the Caribbean). The natural woodland attracts a large variety of wildlife making it ideal for birders or naturalists interested in exploring the Tobago environment. Walk the terraced grounds, explore Englishman's Bay estate, or just relax in the stunning views.

Guest favorite

Villa in Hope estates

4.91 out of 5 average rating, 11 reviews

"Malibu" in Tobago at the Ocean's Edge!

Think 'Malibu in Tobago' and you will know what it feels like to be welcomed into this luxurious penthouse villa at the ocean's edge. This stunning 3-bdrm villa located in Hope Estate, about a 10-min drive from the port in Scarborough, offers an unparalleled oceanfront experience with breathtaking views of the Atlantic and a salt water pool to make Malibu an even more enticing choice. All rooms are air-conditioned and minimally, yet beautifully, appointed with an ocean view.

Guest favorite

The outdoor area features a private pool surrounded by a spacious deck. Two lounge chairs are positioned beside the pool, while the house's exterior showcases large windows and a modern roof design. Lush greenery is visible in the background, adding to the tranquil environment.

Home in Bon Accord

4.92 out of 5 average rating, 106 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

A serene evening view showcases a swimming pool with calming purple lighting, complemented by a unique accent wall featuring artistic windows. A compact outdoor bar area is visible, illuminated softly against the backdrop of the twilight sky and lush greenery along the poolside.

Villa in Crown Point

4.98 out of 5 average rating, 48 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 favorite

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

4.97 out of 5 average rating, 108 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

A swimming pool is visible, surrounded by a stone patio adorned with lush greenery. A wooden pergola is positioned nearby, providing partial shade. Tall palm trees are seen in the background against a cloudy sky, enhancing the serene ambiance.

Apartment in Black Rock

4.96 out of 5 average rating, 25 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

4.94 out of 5 average rating, 108 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.