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Vacation rentals with a pool in Canaan

Find and book unique homes with a pool on Airbnb

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Popular amenities for Canaan rentals with a pool

House rentals with a pool

Guest favorite
A serene view from the interior through large glass doors highlights a private plunge pool. Lush greenery and distant hills frame the scene, with the coastline visible beyond the vibrant foliage under a partly cloudy sky.
Home in Englishman’s Bay
5 out of 5 average rating, 7 reviews

Villa Escalante Tobago's Hidden Gem

SolangeRating, 5 stars7 months ago
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!!!
A modern two-story house is shown with a distinctive red front door. The property is surrounded by well-maintained landscaping, featuring palm trees and colorful shrubs. A spacious driveway leads to a garage with glass doors, and large windows enhance the home's contemporary charm.
Home in Crown Point
5 out of 5 average rating, 4 reviews

Splinterz ~ Your Tobago Escape

JadielRating, 5 stars11 months ago
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!
Superhost
A vibrant sunset paints the sky with shades of orange and purple above a lush green landscape. The view encompasses the distant ocean and various trees, with a spacious villa and neighboring structures positioned in the foreground.
Home in Plymouth
4.94 out of 5 average rating, 16 reviews

Plymouth View Villa: 2br & Pool

ReneeRating, 5 stars2 months ago
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.
A spacious outdoor area features a shared, clear swimming pool reflecting the sun. Lounge chairs are positioned nearby, while a villa structure with large windows is visible in the background. Lush greenery frames the scene, creating a serene escape.
Home in Tobago
5 out of 5 average rating, 3 reviews

Tobago Villa near Buccoo Beach has Stunning Pool

JisselleRating, 5 stars14 months ago
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!
Superhost
The two-bedroom guesthouse features a welcoming living area with soft seating and large windows, allowing natural light to fill the space. A dining area with a table and chairs is adjacent to the kitchen, which showcases modern appliances and ample countertop space.
Home in Scarborough
4.84 out of 5 average rating, 50 reviews

Palm Haven - Home away from home

JeaninnRating, 5 stars7 months ago
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
A charming blue house is nestled amidst a backdrop of lush greenery and tropical foliage. The structure features a sloping roof, vibrant windows, and a balcony that invites natural light while providing a serene atmosphere. Sunlight filters through the leaves, enhancing the tranquil setting.
Home in Carnbee
5 out of 5 average rating, 4 reviews

Outta de Blue

PetrinaRating, 5 stars2 weeks ago
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!
Guest favorite
An open kitchen design features warm wooden cabinetry and modern stainless-steel appliances. A spacious island with seating for six is situated at the center, with contemporary light fixtures hanging above. Window treatments allow for natural light while offering privacy.
Home in Canaan
5 out of 5 average rating, 12 reviews

Amber Villa- Samaan Grove

UniqueRating, 5 stars3 months ago
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.
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, 27 reviews

The Wood House

AmyRating, 5 stars1 month ago
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

Guest favorite
A shared pool is set within a stone-paved area, surrounded by lush greenery and neatly maintained landscaping. Nearby, multiple two-story buildings are visible, creating an inviting atmosphere. The sky features a mix of clouds and blue, adding to the serene environment.
Condo in Buccoo
4.9 out of 5 average rating, 51 reviews

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

HelenaRating, 5 stars1 month ago
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! 🙏
Top guest favorite
A spacious sleeping area features two beds, one larger and one smaller, both dressed in coordinated blue linens. A soft rug lies on the tiled floor, and dark curtains frame the window. A side table with a lamp is placed between the beds, adding functionality.
Condo in Lowlands
4.89 out of 5 average rating, 19 reviews

Lovely loft condo with pool access

BrianRating, 5 stars1 month ago
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.
Superhost
A pool area is featured, showcasing a clear blue swimming pool surrounded by palm trees. A charming gazebo, painted in soft colors, offers seating and shade nearby. Lounge chairs are placed around the pool, inviting relaxation in a tranquil outdoor setting.
Condo in Lowlands
4.69 out of 5 average rating, 121 reviews

Tobago Plantations penthouse: pool beach and golf

CharmaineRating, 5 stars2 months ago
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.
A large shared pool is surrounded by wooden decking and grass. The water is clear and reflects the sky above, featuring a wooden trellis structure along one side. Multiple multi-story buildings are visible in the background, highlighting a spacious outdoor area.
Condo in Buccoo
5 out of 5 average rating, 4 reviews

Dream Island Condo Tobago 2 BedR, 2 BathR, 2 Pools

Denicia-MaeRating, 5 stars1 month ago
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! ❤
Guest favorite
The inviting swimming pool reflects the colors of the sunset, surrounded by a spacious patio. A covered seating area is visible in the background, with palm trees framing the scene. The calm water enhances the tranquil ambiance of the hotel grounds.
Condo in Crown Point
4.88 out of 5 average rating, 8 reviews

Romantic One Bedroom Apartment right on the beach

BrentRating, 5 stars1 week ago
Lovely Ocean view within walking distance to the beach. Listing was spot on and the host was excellent. Highly recommend.
A serene swimming pool is highlighted in vibrant blue, surrounded by tropical landscaping. The well-maintained property features a three-story structure in the background, with lush palm trees gracefully framing the scene. Sunlight dances on the water's surface, enhancing the tranquil atmosphere.
Condo in Black Rock
4.76 out of 5 average rating, 25 reviews

Oceanfront Escape Stunning views Steps to the sand

DanielleRating, 5 stars1 month ago
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!
A private plunge pool is depicted with clear blue water, surrounded by a spacious deck. Several lounge chairs are positioned nearby, offering options for sunbathing or relaxing in the shade of nearby palm trees. Lush greenery frames the scene, enhancing the serene environment.
Condo in Lowlands
4.74 out of 5 average rating, 74 reviews

Golf View Villa 41A (Lower Level)

RobinRating, 5 stars3 weeks ago
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.
Superhost
A rectangular swimming pool is visible, featuring clear turquoise water. Surrounding the pool, a light gray concrete deck offers space for relaxation. The backdrop includes a two-story building with several windows, providing a pleasant view of the outdoors.
Condo in Western Tobago
4.44 out of 5 average rating, 18 reviews

Brand new 2 bedroom with living room & kitchen

ShannonRating, 5 stars12 months ago
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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