
Holiday rentals with a pool in Canaan
Find and book unique homes with a pool on Airbnb
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 $89 SGD per night before taxes and fees

Verified guest reviews
Over 790 verified reviews to help you choose

Family-friendly holiday rentals
40 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!
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 🤍

Buccoo Luxe Escape|3BR Condo w/Pool & Modern Charm
Welcome to Aurelia - a radiant escape where tropical serenity meets quiet luxury. Featuring warm natural finishes with sleek contemporary lines, Aurelia invites you to slow down and reconnect in refined comfort. This newly furnished 3-bedroom condo is artfully designed for families, friend groups, or long-stay guests seeking a luxurious escape close to beaches and island attractions. Relax in the open-plan living area with comfortable lounge seating and doors that open to your private balcony.

Stylish Getaway Near Beaches. Quiet. Pool. Jacuzzi
Enjoy comfort and privacy in this spacious, modern apartment set in a quiet, safe community close to beaches, dining and nightlife. Perfect for professionals or couples, the space features a queen-size bed, cozy living area with Smart TV, fast Wi-Fi, fully equipped kitchen, large bathroom with massage shower, hot water, and private balcony. Guests also enjoy access to a swimming pool and jacuzzi—ideal for relaxing after work or a day out. We look forward to helping you make your visit memorable.

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.

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!

Tobago Villa near Buccoo Beach has Stunning Pool
Although this stunning villa with its beautiful pool sleeps 10, the price quoted is for 6 persons. Each additional guest is $25 per night. If your family is bigger than this, feel free to ask about booking the adjacent one-bedroom Chalet for an additional US$100 per night. While the bedrooms are air-conditioned, the main living areas - living/dining room, porch and kitchen - of the Villa are cooled by ceiling fans and island breezes coming through the open windows and doors.

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

Tradewinds Villa
Forget your worries in this spacious and serene Villa. Tradewinds Villa is a newly built quality home designed by a local respected Architect and is located in the up-scale development of Samaan Grove which is complemented by 24 hour security. Tradewinds can sleep 10 adults in comfort. All rooms have their own en-suite and has AC. The large kitchen with its elegant walnut finish gives you the perfect environment to entertain your close families and friends.

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

Plymouth View Villa: 2br & Pool

Plantation View Villa

Villa Delphinae

Oceanview Townhouse · Plunge Pool + 4 Ensuites

Eagle's Base Villa with Spectacular Views-12-38

Fairways Villa - Mt Irvine Tobago Charm

Uprise Villa

Outta de Blue
Apartment rentals with a pool

Lovely loft condo with pool access

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

Canoe Bay Studio-Cocrico

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

Private Saltwater Pool Lovely 2 bedroom Suite

Romantic One Bedroom Apartment right on the beach

Buccoo Escape - 2 bedroom cozy condo near beach

Golf View Villa 41A (Lower Level)
Other holiday rentals with a pool

2 BR steps to the beach, & pool.

BotanicsGarden Suite with views of the nylon pool

Samaya Villa

Bay Apartment at Sandy Point

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

Bahari Blu Tobago Saltwater pool? Beach or both?

Villa Augustus

Luxury villa, pool and the best botanical garden!
When is the best time to visit Canaan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $322 SGD | $322 SGD | $322 SGD | $252 SGD | $253 SGD | $259 SGD | $332 SGD | $332 SGD | $310 SGD | $338 SGD | $253 SGD | $255 SGD |
| 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 |
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