
Holiday 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 🤍

Firefly Villa - 'Roots'
A spacious, modern, beautifully decorated home with a zen vibe and an inspiring location for working away from home. ‘Roots’ has two cozy double bedrooms, comfortable work spaces and fully-equipped kitchen with kitchen island, and deluxe double fronted fridge, en-suite bathrooms and wooden floors. Lie by the infinity pool and watch as a bright blue-grey tanager flies right over your head from one tree to the next. The perfect blend of treehouse and charming, stylish Caribbean poolside villa.

Casa Bon - a charming Bon Accord home
Casa Bon offers all the comforts you need in a Caribbean holiday home! It is conveniently located in the Bon Accord area and is walking distance to Store Bay and Pigeon Point - two of Tobago's most popular beaches. This charming Spanish-style villa is set in lush, tropical gardens and has four air conditioned bedrooms, three of which have ensuite bathrooms. The open plan living and dining rooms flow right onto the patio and pool deck complete with a free form swimming pool and attached spa.

Sea View Villa Cluster 63A(2BR,Pool,Wifi,Golf)
Sea front villa with scenic entrance near the Magdalena Hotel with an international Golf Course. Minutes away from iconic beaches and shopping malls. Furnished, 2 bedrooms with upgraded ensuite bathrooms, open concept, and a private pool with sundeck on the ground floor of the duplex. Gated community(manned 24 hours) Fully air-conditioned along with ceiling fans & Netflix. Contains outside bathroom and utility room. * Maid service available at an additional charge.(Mandatory after 3nights)

TheNest 5BR Villa (16 ppl)Pool-Garden-SwingHammock
Welcome to The Nest Villa, a tropical retreat in Tobago, located near No-man's land, Mount Irvine, Pigeon Point, & Buccoo beaches. This 5 bedroom house promises relaxation & adventure. Explore the island by car, scenic walks & trail bikes, or relax by the pool surrounded by the lush large garden. Samaan Grove is a Gated Safe Community, Kid-friendly, delight in the swing set. Discover the hidden gem, to unwind & soak up the sun. Warm Hosts with Insider tips with ensure an unforgettable stay!

Villa Mila #35
This property is located in Samaan Grove, Golden Grove, Canaan, Tobago. A secure gated community which consists of a large number of high-end villas, used for both personal and rental purposes. As you enter the development, it possesses a relaxing ambiance surrounded by lakes, trees and stunning landscaped gardens throughout. This beautiful villa has a private swimming pool with a patio. This area is a perfect area for liming with family/friends or just relaxing with a glass of wine.

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 warm and private salt water pool.

Villa Oceana - Luxury Holiday Villa
Villa Oceana is a luxurious and spacious holiday villa in the popular gated community of Samaan Grove. Located in the southwest of the island, Samaan Grove is close to both the activity of Crown Point with its restaurants, nightlife and the world-famous Pigeon Point beach as well as being a stone's throw from the Mt. Irvine Golf Course and the beautiful beaches at Mt. Irvine Bay and Grafton.
Popular amenities for Canaan rentals with a pool
House rentals with a pool

Couple’s hideaway, Castara

Plymouth View Villa: 2br & Pool

Tradewinds Villa

Stylish Oceanview Townhouse in Tobago

Tobago Villa near Buccoo Beach has Stunning Pool

Fairways Villa - Mt Irvine Tobago Charm

Villa by Pigeon Point Paradise

Outta de Blue
Apartment rentals with a pool

Buccoo Luxe Escape|3BR Condo w/Pool & Modern Charm

Lovely loft condo with pool access

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

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

Diamond-ADA Friendly, 5-8mins to beach/airport

Private Saltwater Pool Lovely 2 bedroom Suite

Buccoo Escape - 2 bedroom cozy condo near beach

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

Jazuri Couple Villa

Quiet, Modern Apartment with Poolside View

Sand Dollar Cove Vacation Villa

Poui Place - 4 Bd villa in Samaan Grove, Tobago

Bay Apartment at Sandy Point

Frangipani Villa- Lovely 3 Bedroom, Pool, Fully AC

Saltwater Pool, Lush Garden, 5-10 min walk Beaches

Bahari Blu Tobago Saltwater pool? Beach or both?
When is the best time to visit Canaan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £244 | £145 | £146 | £148 | £148 | £152 | £195 | £195 | £182 | £199 | £148 | £150 |
| Avg. temp | 27°C | 27°C | 27°C | 28°C | 29°C | 28°C | 28°C | 28°C | 29°C | 28°C | 28°C | 27°C |
Quick stats about holiday rentals with a pool in Canaan

Total holiday rentals
Explore 50 holiday rentals in Canaan

Nightly prices starting at
Canaan holiday rentals start at £45 per night before taxes and fees

Verified guest reviews
Over 710 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Canaan holiday rentals include wifi 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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