
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.

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.

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.

Poui Place - 4 Bd villa in Samaan Grove, Tobago
Escape to a private oasis at this exquisite 4-bedroom villa, nestled in a serene and exclusive location. Designed for those seeking the perfect blend of luxury and relaxation, this villa offers spacious living areas, premium amenities and modern décor with an abundance of natural light. The highlight of the villa is the sparkling outdoor pool, complete with a floating pavilion ideal for al fresco dining. Families will especially appreciate the wading pool, perfect for the little ones.

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.

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.

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.

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.

Diamond-ADA Friendly, 5-8mins to beach/airport
This newly renovated unit is perfect for extended family stay or small group trips. Its ambience both inside and outside, provides a convenient and accessible access to family inclusion and bonding time without sacrificing safety or ambience. Ideally located near to the conveniences of the Buccoo and Mount Irvin beach facilities, Shirvan plaza and Shirvan police station.
Popular amenities for Canaan rentals with a pool
House rentals with a pool

Couple’s hideaway, Castara

Plymouth View Villa: 2br & Pool

Plantation View Villa

Stylish Oceanview Townhouse in Tobago

Fairways Villa - Mt Irvine Tobago Charm

Uprise Villa

Outta de Blue

Amber Villa- Samaan Grove
Apartment rentals with a pool

Lovely loft condo with pool access

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

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

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 holiday rentals with a pool

Nirvana Tobago Villa Saltwater Pool & Ocean View

2 BR steps to the beach, & pool.

Pleasant Cove: Luxe Villa w. Private Beach

GOLF BEACH VILLA

BotanicsGarden Suite with views of the nylon pool

by Felice

Villa Augustus

Expansive deck! Luxurious super king beds!
When is the best time to visit Canaan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £241 | £144 | £144 | £146 | £147 | £150 | £192 | £192 | £180 | £196 | £147 | £148 |
| 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 £52 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!
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