
Holiday rentals with a pool in Western Tobago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Western Tobago
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 🤍

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.

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.😉

Carlton’s Haven at Robyn’s Nest
Carlton’s Haven at Robyn’s Nest Tucked away in the tranquil village of Union, Tobago, Carlton’s Haven is a modern two bedroom, two bath, condo style duplex designed to make you feel completely at ease. Surrounded by lush greenery, the soothing sounds of birds, and cool island breezes, it’s your perfect escape into nature while still enjoying contemporary comfort and style. A 5-minute drive from Scarborough our capital putting local markets, beaches, and cultural gems right at your fingertips.

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.

Apas On The Hill: One Bedroom Apartment 1
Welcome to "Apas On The Hill". Nestled in the quiet Signal Hill area, we are located approx. 4 Kms from the sea port at Scarborough and 11 Kms from the ANR Robinson International Airport. Enjoy peace and tranquility while being in a safe, private and comfortable environment. Our rooms (apartments) are cozy, yet elegant, spacious and comfortable. Each apartment comes with a fully equipped kitchen, outfitted with modern appliances, Wi-Fi, hot and cold water, cable TV, linen and towels.

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.

Stylish 2BR Condo w/ Pool Near Buccoo Beach
Welcome to The Cocoa Condo. A unique two-bedroom condominium, located on the gated compound of the newly constructed Buccoo Homes Phase 2. This unit is mere meters from the Buccoo Food Court and a 15-minute walk to explore the renowned Buccoo family-friendly beach, the protected Buccoo Reef, and the shallow, crystal-clear "Nylon Pool". Popular activities include glass-bottom boat tours, horseback riding in the ocean, and the lively Sunday School goat and crab races.

Villa Escalante Tobago's Hidden Gem
If you’re searching for an experience then this is your destination!! Villa Escalante is a modern architect designed gem, nestled in the Main Ridge Forest. The Villa is designed to capture the view of Englishman’s Bay and the Main Ridge, a perfect spot for viewing both the flora and fauna. The Main Ridge Forest is a designated UNESCO biosphere reserve. The architect designed the villa so that nearly every living space has a 180-degree view.

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.

Sunset on the ocean
This apartment is unique in the Tobago short term rental space. Brand new, stylish "island chic" place offers ocean views and is right above one of the most stunning Tobago beaches. You have ample space for your family or as friends to enjoy spacious living and dining space, top of the art kitchen. The two bedrooms and 2.5 bathrooms give you the space to enjoy this calm yet very well located new spot.
Popular amenities for Western Tobago rentals with a pool
House rentals with a pool

Villa Narain, Tobago

Villa Anhinga

Plymouth View Villa: 2br & Pool

Tradewinds Villa

Villa Delphinae

Oceanview Townhouse · 4 Ensuites + Plunge Pool

Beautiful villa nr Castara & beach

Villa Bimiti Mt Irvine with stunning Pool nr Beach
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

Canoe Bay Studio-Cocrico

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

Private Saltwater Pool Lovely 2 bedroom Suite

Hibiscus Suite at Black Rock Dreams

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

Xanadu • Scenic Views + Private Waterfall

Buccoolito 2B - Modern Condo w/Pool | Near beach

Pleasant Cove: Luxe Villa w. Private Beach

Island breeze penthouse

177 Sea Shell Villa, Tobago W.I.

Villa Blue Moon

Bahari Blu Tobago Saltwater pool? Beach or both?

Emerald's Cove
Destinations to explore
- Oistins Holiday rentals
- Les Trois-Îlets Holiday rentals
- Fort-de-France Holiday rentals
- Holetown Holiday rentals
- Lecherías Holiday rentals
- Le Diamant Holiday rentals
- Bridgetown Holiday rentals
- Port of Spain Holiday rentals
- Sainte-Luce Holiday rentals
- Saint George's Holiday rentals
- Tobago Holiday rentals
- Sainte-Anne Holiday rentals
- Smoking-friendly rentals Western Tobago
- House rentals Western Tobago
- Rentals with a patio Western Tobago
- Flat rentals Western Tobago
- Villa rentals Western Tobago
- Private suite rentals Western Tobago
- Family-friendly rentals Western Tobago
- Waterfront rentals Western Tobago
- Rentals with a hot tub Western Tobago
- Pet-friendly rentals Western Tobago
- Rentals with beach access Western Tobago
- Serviced apartment rentals Western Tobago
- Rentals with a washing machine and dryer Western Tobago
- Rentals with a firepit Western Tobago
- Bed and breakfasts Western Tobago
- Apartment rentals Western Tobago
- Aparthotel rentals Western Tobago
- Rentals with outdoor seating Western Tobago
- Hotel rooms Western Tobago
- Guest house rentals Western Tobago
- Beachfront rentals Western Tobago
- Rentals with pools Tobago
- Rentals with pools Trinidad and Tobago





