Vacation rentals with a pool in Trinidad and Tobago

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Top-rated rentals with a pool in Trinidad and Tobago

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

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Guest favorite

Condo in Tobago

4.9 out of 5 average rating, 31 reviews

Premium Condo Accommodation at Tobago Plantations

Located in the prestigious gated community of Tobago Plantations. This location is great with 10 minutes drive to Pigeon Point, Store Bay, restaurants, shops and nightlife in Crown Point. Condo is fully furnished with great amenities. Two large bedrooms with two queen size beds in each room. To accommodate 8 guests. Access to three (3) shared pools, twenty four hour security, view of ocean and golf course, dedicated parking, high speed internet and Netflix on (3) 65" flat screen televisions.

Superhost

Condo in Petit Valley

4.81 out of 5 average rating, 16 reviews

VClose to POS Home away from H :Peaceful 2BR Apt

Nestled in the hills yet close to the city, unwind at our cozy, peaceful oasis with hill views, beautiful sunsets &ocean views.. Modern Ground floor apartment: 2 bedrooms each with its owndesignated workspace , Queen beds , 2 full baths, fully air conditioned, fully equipped kitchen. Washing machine & dryer, Open living space which opens on to pool deck. Ping-Pong Table, Board Games. Close proximity to POS, shopping malls, banks, cinema, grocery, Pharmacy. Access to Food delivery services

Guest favorite

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.

Guest favorite

Villa in Canaan

4.93 out of 5 average rating, 30 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.

Guest favorite

Home in Gulf View

4.93 out of 5 average rating, 14 reviews

The Fountain

This older home with quaint charm was built in the 1950's. Much of the original architecture has been retained. The mid-century design and architecture, arched entrance door, wooden ceilings and jalousied closets will appeal to the most discerning taste. As you enter, you would be greeted by a stunning view of the Gulf of Paria. On a clear day, you could see Venezuela. Why not enjoy the private pool with playful mosaics of dolphins and sea horses? Come on down. La Fuente awaits!

Top guest favorite

Apartment in Port of Spain

4.96 out of 5 average rating, 26 reviews

Perfect location/ Pool - White Sand Apt

Welcome to “Sands of Time”, a secure compound with beautiful apartments. This apartment, which is named “White Sand” is perfect if you like a little bit of everything. Top-tier location. Comfortable living. Stylish and modern amenities. A place to retreat. You can choose to enjoy coffee on your private patio or lounge by the poolside. Also, if you are a nature lover, take advantage of the patio between 4:30 -5:30 pm as you see flocks of birds returning to their homes.

Guest favorite

Home in Bon Accord

4.92 out of 5 average rating, 106 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.

Superhost

Apartment in Black Rock

4.77 out of 5 average rating, 39 reviews

Condo on the BEACH

This apartment is horizontal with the house as it is frontier towards the beach. The verandah has a top tier view of the ocean and pool. Entering into the living room and kitchen which is more of the garden view. The bed room have a beautiful view over looking the infinity pool and the ocean back drop. The apartment consists of dual colors to create a clam and peaceful ambience as to keep a cool comfort feeling. Please note the pools is shared with two other units.

Superhost

Home in Las Lomas #2

4.87 out of 5 average rating, 192 reviews

Nature Getaway Resort with private pool

Lovely 2 bedroom home plus loft with resort type amenities tucked away in the woods but just a 10 min drive from the airport. The house comes equipped with a full kitchen which includes - Gas burner stove/oven, double door refrigerator, dish washer, microwave and toaster oven. All utensils and cookware is included. There is a private pool (heated if required) with gazebo. There are four (4) hammocks for relaxing, kids play park with two slides and swings.

Guest favorite

Home in Canaan

4.9 out of 5 average rating, 20 reviews

Flamingo Villa Tobago-sleeps 14

Experience the epitome of elegance and luxury in this stunning 4-bedroom villa, nestled within a serene and secure gated community. Ideally located just moments from the airport and pristine, sun-kissed beaches, this exquisite retreat offers the perfect blend of sophistication, comfort, and convenience. For larger groups, the adjacent Sea Glass Villa—accessible via a private gated entrance—offers an exceptional opportunity to expand your accommodations.

Guest favorite

Apartment in Crown Point

4.87 out of 5 average rating, 45 reviews

Modern studio on Crown Point strip- Suite

Enjoy a stylish experience at this central location. This 1 bedroom can accommodate 4 persons, with 2 double beds , 1 bathroom and 1 kitchenette. Each room has a private hot tub with resort pool access. Our units are located in the heart of Crown Point next to all of the major bars, restaurants and beaches. Walk to Jade Monkey bar or simply walk around Crown Point. Does get loud on weekends. Guests cannot be sensitive to noise.

Top guest favorite

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.