Vacation rentals with a pool in Tobago

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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 lush green lawn is seen in front of the villa, framed by tropical plants and flowering shrubs. The outdoor space includes a patio area with tables and chairs, along with a pool that invites relaxation. The vibrant colors of the surroundings create a refreshing atmosphere.

Apartment in Bon Accord

4.88 out of 5 average rating, 161 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.

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Villa in Lowlands

4.85 out of 5 average rating, 53 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.

Superhost

A spacious outdoor gazebo is featured, complete with a comfortable seating area and an outdoor television. The design allows for easy access to the inviting heart-shaped pool, which is surrounded by lush greenery, enhancing the relaxing atmosphere of the property.

Villa in Canaan

4.88 out of 5 average rating, 40 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.

Superhost

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

4.8 out of 5 average rating, 98 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

An infinity pool extends across a wooden deck, reflecting the sky and surrounding greenery. Two lounge chairs are positioned near the water's edge, shaded by large umbrellas. The scene is set against a backdrop of trees and a distant landscape under a soft, warm light.

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

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, 118 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.

Guest favorite

The living area is framed by large windows overlooking a pool and views of the lagoon. Two wooden chairs with blue cushions are positioned beside a wooden coffee table, while natural light fills the space, highlighting the woven rug and surrounding tropical scenery.

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.

Top 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

A spacious outdoor area features a clear blue pool surrounded by lounge chairs. Lush greenery and colorful plants enrich the environment, while a well-designed villa stands in the background. The sun-drenched atmosphere highlights the inviting design and layout of the space.

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

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, 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

A serene pool area is surrounded by lush tropical greenery, creating a tranquil oasis. The clear water reflects the blue sky dotted with fluffy clouds. Comfortable seating options are located nearby, inviting guests to relax and enjoy the natural beauty of the landscape.

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.

Superhost

A private pool with clear blue water is surrounded by a wooden deck. Comfortable lounge chairs are positioned nearby, offering views of the ocean and lush greenery. The peaceful atmosphere is enhanced by the calm waters of the sea visible in the background.

Bungalow in Lowlands

4.89 out of 5 average rating, 64 reviews

Ocean Front Cottage, Petit Point

My place is right on the ocean, and close to a golf course and restaurants. You’ll love it because of the outdoor space, the neighborhood, the ambiance, and the fact that it's on the sea. It's safe and secure, and is next to kayaking, stand up paddling, walking, jogging. My place is good for couples, business travelers, and families (with kids).