
Holiday 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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Popular amenities for Tobago rentals with a pool
House rentals with a pool

Plymouth View Villa: 2br & Pool
Junior’s place was so nice that I had to do it twice! Revisiting felt like coming back home. Just like my first stay, the place was nothing short of amazing. Junior has maintained his friendliness and was accommodating and flexible. Will definitely be back for a third time and as many times as my schedule allows.

Beautiful villa nr Castara & beach
We just spent the most amazing eight days at Tanager Ridge. Words can't truly capture how magical this place is. Spacious, secluded and equip with every amenity imaginable. The design and decor lends itself to an idyllic Caribbean getaway feel. If you enjoy being surrounded by nature and awe-inspiring views, this is the place for you. N.B. the pool is addictive lol. Both Sheba and Jango were so lovely. Sheba was always a message away and Jango is a gem - very humble and knowledgeable about the area. We were grateful for his presence on the compound, especially at nights...and the fruits and limes he provided from the garden. Thank you Jamie & Sarah for being courteous and responsive hosts. We look forward to returning! Janessa & Javid.

Tobago Villa near Buccoo Beach has Stunning Pool
Our stay at the villa was wonderful! From the moment we arrived, we were warmly greeted and awed by the private tranquility and beauty of the surroundings. The villa is stunning, boasting a peaceful ambiance and gorgeous decor. One of the highlights of the villa is the pool, which was consistently warmed to perfection. Whether it was a refreshing morning swim or a relaxing evening dip, the pool provided hours of enjoyment for our family. Additionally, the array of board games provided endless entertainment and the TVs in every room were a hit with the kids! Maria and Donna showcased outstanding hospitality. They were incredibly helpful and kind throughout our stay. While our experience was very positive, the lack of a bathroom downstairs posed a minor inconvenience, especially when coming out of the pool to use the bathroom and having to go upstairs. However, this can be remedied by renting the smaller pool house along with the larger chalet. We would highly recommend this villa!

Modern Hillside Villa with Panoramic Ocean Views
Ideally located. Shott walk fron a couple of lovely beaches. Easy drive from other hot spots. Hosts were really kind and responsive. Checked in on us and helped with any minor issues. Really flexible and made brilliant recommendations. Wonderful private outdoor space with uninterrupted views to the sea. Great value for money.

Palm Haven - Home away from home
An enjoyable stay! Dernelle is great! She has been extremely helpful. She created these amazing informative pamphlets that tells you house rules, nearby restaurants, attractions, transportation help, and much more. She’s also a fabulous makeup artist amd will have you looking spectacular for Tobago Carnival! I recommend her home

Villa Escalante TBGO Lower Level
My wife and I and our 7yo boy stayed at Donna’s apartment which is modern, functional, spacious and very well appointed. I am 60 yo, very well-travelled having lived on several continents and I can attest that the beach and jungle views from the house rank amongst the finest home views I have ever witnessed. It is the only house in the vicinity of the pristine and untouched Englishman’s bay rainforest and beach and it is very peaceful and truly mesmerising. Donna proved a very proactive and efficient host. We stayed in two other places in Castara and Parlatuvier which were excellent as well but this topped them all. We would have happily stayed quite a while longer than our 4 days. Highly recommended.

Outta de Blue
Loved the quality of the building, the architecture and the use of local woods. Very airy, open floor plan for the living and dining area. If I had to hide away for an extended period to relax this would be a most comfortable place. Thoroughly enjoyed our stay!

Amber Villa- Samaan Grove
Lovely clean house! Beautiful gated community. Host was very responsive and clear instructions for check in. Kindly allowed us to have a late checkout as we had a late flight so very flexible! Only downside was jacuzzi wasn’t heated and pool lights kept cutting off.
Condo rentals with a pool

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6
Our stay at Neal's Airbnb was truly excellent! 👍 He thought of everything we could possibly need, from kitchen gadgets to plenty of towels. The condo itself exceeded our expectations – so spacious and impeccably clean! ✨ We must say, the pictures don't do justice to how lovely the place truly is. The kids especially loved the pool, which was just the right depth for them. ☀️🏊♀️ Just a small note, we felt the kitchen could benefit from a little more lighting and the light in the king's bedroom was coming off on its own intermittently. 💡 But aside from that minor point, everything was absolutely wonderful. We're already looking forward to returning to Tobago and hope to stay at your place again, Neal! 😊 Many thanks! 🙏

Villa Reina Tobago Plantations. Pool, Golf, Ocean
Comfortable and safe. Great location if staying with young kids. Will definitely book again.

Tobago Plantations penthouse: pool beach and golf
Thoroughly enjoyed our stay! Great space for 2 people. Loved the constant sea breeze, great views, having a kitchen and a dining table to relax while eating our meals. The only challenge is the lack of a washing machine so pack enough so you won't need to wash. A very clean relaxing space which i would recommend while exploring the beautiful island of Tobago.

Private Saltwater Pool Lovely 2 bedroom Suite
Our stay at Sharlene's place was extremely pleasant. While the space is not sprawling, it is thoughtfully laid out and possesses all the amenities one could need for a short Tobago trip. The space is serene and private and was extremely clean and inviting. Host is helpful and responsive. Would definitely consider staying here again.

Penthouse in Tobago Plantations
Treece's place was absolutely perfect and exceeded expectations. Will definitely recommend and stay again.

Oceanfront Escape Stunning views Steps to the sand
Stunning location on one of the most beautiful beaches. Nice calm water on the bay side, and fun waves on the other end of beach. Gorgeous sunset! Beach was also great for running or walks! The place was immaculate, 3 spacious bedrooms and 3 full bathrooms/showers. A very large master bedroom with views of the sea! Gorgeous all around, cannot wait to go back!

Golf View Villa 41A (Lower Level)
My buddy and I stayed here because we were playing in a golf tournament which was close by. We could actually see the golf course from where we stayed. We didnt make use of all the amenities but they were there to be used. No issues whatsoever.

Brand new 2 bedroom with living room & kitchen
My stay here, though short, was very comfortable. The place was nice and clean, just as in the pictures. Communication with the host was also very easy. All listed amenities (kitchen, washer and dryer, towels, hot water, wifi, etc.) were included and the pool was nice. It is located within relatively close to the beaches, food vendors and supermarkets so that it is not difficult to access anything. I would definitely stay here again. It was a nice getaway
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