
Vacation rentals with a pool in Canaan
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Canaan
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Cardinal Villas Tobago-Bram Villa, Samaan Grove
Our Villa is located in the gated community of Samaan Grove Tobago. One of the few gated communities. The villa itself is comfortable and spacious and just feels like a home away from home. The surroundings are lush and peaceful with birds chirping and beautiful greenery. Our outdoor patio invites you to unwind and relax and have fun pool days with family and kids absolutely love it. Finally connect to our Bluetooth fan lights on our patio, and enjoy your favorite playlist while enjoying the company of your party, taking a nap on the patio or swimming in the pool. Come experience a truly relaxing vacation disconnecting from the “busyness” of life and connecting with those that matter 🤍

Citrine-Dreamy mall studio unit
This unique place has a style all its own. If you’ve ever wanted to be at the heart of it all, yet in your own dreamy getaway, this stylish modern studio apartment unit is just right for you. Located on the top floor of the distinct architecture of the D’ Colluseum Mall in Crown Point, Tobago, this unit has access to the most renowned beaches of Pigeon Point and Store bay beach facilities and its own in-house gym, to maintain that toned figure. Want to create a chill mood? Just ask Alexa.😉

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.

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.

Beach Retreat: Central Crown Point Condo
Location, location, location! No need for a car in this secure 1 bedroom condo based in the heart of Crown Point. Enjoy quick and easy access on foot to countless restaurants and take-out options, shops, ATMs, nightlife and South West Tobago’s most beautiful and popular beaches. Equipped with a full kitchen, shared pool, washer/dryer, 50 inch Smart TV, queen sized bed, pull out twin day bed and A/C throughout. Come “retreat” from the beach at this cozy condo in the heart of Crown Point!

Guest Favourite - The Balcony, 4B Buccoo, 2BR Apt
Explore our stylish condo in Buccoo, with onsite restaurants and a coffee shop, just 7 minutes drive from Buccoo Bay, 10 minutes from Grafton and Mt Irvine beaches and Golf Course. Approx 15 minutes from Pigeon Pt and Store Bay beaches. Experience modern comfort, strategically placed for effortless exploration of Tobago's treasures; Nylon Pool, Argyle Waterfall, scenic drive through the rain forest to list a few. Sea Horse, Waves and Fish Pot restaurants all within 10 mins drive.

Oceanview Villa w/ Infinity Pool
Enjoy a relaxing escape at our oceanview villa. Nestled in a gated community, this serene retreat features magnificent ocean views and an infinity edge pool. The villa comfortably sleeps 6, with 3 spacious bedrooms and 3 full bathrooms, providing plenty of room to unwind. With private parking and the security of a gated setting, it’s perfect for families, friends, or couples seeking comfort and stunning views. Make your stay memorable in this well-appointed home away from home.

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.

Sea Glass Villa Tobago-sleeps 12
This is a very beautiful and private Villa, the beds are super comfy, all bedrooms are ensuite and the Kitchen is fully equipped, it is truly a home away from home The Villa sleeps a max of 12 persons including kids, the price is based on Occupancy, please book for the correct number of persons to get the exact cost. The base price is on 4 persons, every person thereafter is $15 per person per night, this is structured so that smaller groups do not pay the full price.

Villa Blue Moon
Make memories at this unique and family-friendly place. A 4 bedroom 10 person villa located in secured compound close to beaches, bars and restaurants. With fun activities such as pool table, basketball, heated jacuzzi, swimming pool, 3 televisions, modern fully equipped kitchen, laundry room with washer & dryer, comfortable family room and Hi-Fi stereo system. A playful, open and entertaining home to feed your senses, to enjoy and unwind as you will

Island breeze penthouse
Forget your worries in this elegant, beautiful and relaxing space. Our penthouse is located at Building 9, Apartment 4D. Sip your coffee in our balcony while enjoying the morning island breeze and a view of the pool. You will find delicious doubles just in front of the compound and the best chicken sandwich from Block 22. Enjoy both pools, one in the morning and the other in the evening. There is a gym, one minute away, next to to the food court.

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.
Popular amenities for Canaan rentals with a pool
House rentals with a pool

Couple’s hideaway, Castara

Plymouth View Villa: 2br & Pool

BACOLET BLISS

Villa Delphinae

Stylish Oceanview Townhouse in Tobago

Beautiful villa nr Castara & beach

Eagle's Base Villa with Spectacular Views-12-22

Villa Escalante TBGO Lower Level
Condo rentals with a pool

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

Lovely loft condo with pool access

Tobago Plantations penthouse: pool beach and golf

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

Private Saltwater Pool Lovely 2 bedroom Suite

Hibiscus Suite at Black Rock Dreams

Buccoo Escape - 2 bedroom cozy condo near beach

Romantic One Bedroom Apartment right on the beach
Other vacation rentals with a pool

Apartment on the beach, Netflix digital cable Wifi

Pleasant Cove: Luxe Villa w. Private Beach

Coker Cabana - Tobago

Bay Apartment at Sandy Point

Amber Villa- Samaan Grove

Mary's Hill Guest house

Bahari Blu Tobago Saltwater pool? Beach or both?

by Felice
When is the best time to visit Canaan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $325 | $194 | $195 | $197 | $198 | $203 | $260 | $260 | $243 | $300 | $295 | $313 |
| Avg. temp | 80°F | 80°F | 81°F | 83°F | 83°F | 82°F | 82°F | 83°F | 83°F | 83°F | 82°F | 81°F |
Quick stats about vacation rentals with a pool in Canaan

Total vacation rentals
Explore 50 vacation rentals in Canaan

Nightly prices starting at
Canaan vacation rentals start at $60 per night before taxes and fees

Verified guest reviews
Over 700 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Canaan vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Canaan rentals

4.8 Average rating
Canaan stays are highly rated by guests—averaging 4.8 out of 5!
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