
Vacation rentals with a pool in Canaan
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Top-rated rentals with a pool in Canaan
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Canaan rentals with a pool
House rentals with a pool

Villa Escalante Tobago's Hidden Gem
Villa Escalante is the epitome of peace, calm and serenity. The views are outstanding, the house is well organized, architected and brilliantly thought out. Our hosts graciously stocked the home with all the necessary amenities for both the baths and kitchen, and my family and I were very comfortable. It is the perfect location, if you need to runaway for an escape and enjoy nature sounds, the beach and a pool. Def staying here again. Donna and her hosting staff were communicative , friendly and always available. I have left Tobago lighter and more relaxed. Thank You again!!!

Splinterz ~ Your Tobago Escape
Tobago has lots of Villas but this one is right up there with the best! Firstly, the host was responsive and Kirk (the one who checks you in) was friendly and extremely helpful. The villa was huge with lots of space in every room throughout the villa. The pool and other common spaces were well laid out for lounging and everything in general was aesthetically pleasing. I would 100% return!

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.

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!

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

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.

The Wood House
As a couple of nature lovers, this place was perfect. We loved sitting on the veranda watching the parrots fly past and the hummingbirds flit through. We ended up spending way more time at the house than we anticipated just because it was so tranquil and relaxing. The pool was well maintained and much needed in the heat and the perfect depth for lounging about with a rum punch. Terry was very responsive whenever we messaged and although he was not on site, he relayed any issues to Gloria & Byron who were able to help. Top tip - the washing machine is in a locked outbuilding so let Gloria know if you need to use it and she will give you access. We did find there were a few mosquitos out in the morning and evening so recommend bringing some insect repellent if you want to sit outside (or just stay in the pool to avoid them!) Maya the cat was an absolute sweetheart and we couldn't believe she wanted to sit on our laps in 30C heat 😻. We hope to visit again in the future.
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! 🙏

Lovely loft condo with pool access
Treece is a super host. We reported a small problem and within a couple of hours she found the solution. The apartment was well maintained and we felt right at home.

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.

Dream Island Condo Tobago 2 BedR, 2 BathR, 2 Pools
Our family had such a special time here. The space was cozy, clean, and welcoming. It was perfect for relaxing and enjoying quality time together. The hosts even provided family games, which added such a fun and thoughtful touch to our stay. Ishani was extremely kind and flexible, always making sure we felt at ease. The pools were a big hit, offering plenty of fun for both kids and adults. The location was also ideal, just a short drive to beautiful beaches and only a 2-minute walk to a nearby food court with plenty of great dining options. Truly a place that felt like a home away from home. We’re so grateful for the experience and the memories we made. We would definitely be back! ❤

Romantic One Bedroom Apartment right on the beach
Lovely Ocean view within walking distance to the beach. Listing was spot on and the host was excellent. Highly recommend.

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
Quick stats about vacation rentals with a pool in Canaan
Total rentals
50 properties
Nightly prices starting at
G$12,539 GYD before taxes and fees
Total number of reviews
570 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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