Holiday rentals with a pool in Tobago

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Tobago

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

The exterior of the villa is presented, featuring a sloped roof and vibrant orange window frames. A green wooden fence encloses the property, complemented by neatly trimmed hedges and a manicured lawn, which adds to the welcoming ambiance of the gated community.

Villa in Canaan, Tobago

4.94 out of 5 average rating, 48 reviews

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 🤍

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Top Guest favourite

Condo in Buccoo

5.0 out of 5 average rating, 29 reviews

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.

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Guest favourite

A shared pool is framed by a stone patio, reflecting the nearby condominium. Lush greenery and ornamental plants enhance the surroundings. The modern two-level building in the background features multiple balconies and large windows, allowing for natural light to illuminate the interior spaces.

Condo in Buccoo

4.86 out of 5 average rating, 90 reviews

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

Your perfect getaway 2 level condo with 3 bedrooms, 2.5 baths in a gated community behind the Buccoo Strip Mall off Shirvan Road. Shared pool on compound, balcony views and a short drive away from Buccoo Bay and Mt Irvine Beach and Mt Irvine Golf Course. Experience all the attractions of beaches, golf, horseback riding, glass bottom boat rides, Easter Sunday Buccoo Goat Races, Sunday School street parties, mouth watering local cuisine and the getaway experience in a brand new comfortable condo!!

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Guest favourite

The two-story villa features a warm orange exterior with arched balconies and a tiled roof. A freeform pool is visible in the foreground, accompanied by a spa. Several sun loungers are positioned around the pool, while lush greenery frames the property.

Home in Bon Accord

4.75 out of 5 average rating, 110 reviews

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.

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Guest favourite

The exterior of a modern villa is displayed, featuring a spacious upper balcony with white railings above large glass doors. Lush greenery surrounds the property, and a private pool is visible on the lower level, creating a serene outdoor atmosphere.

Villa in Lowlands

4.84 out of 5 average rating, 101 reviews

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)

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Top Guest favourite

A wrap-around balcony offers panoramic views of the sunset over lush tropical trees and the Caribbean Sea. Floor-to-ceiling glass doors line one side, inviting natural light and providing easy access to the outdoor space.

Apartment in Bethel

4.97 out of 5 average rating, 184 reviews

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.

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Guest favourite

Villa in Mt. Irvine

5.0 out of 5 average rating, 8 reviews

TheCasaVilla 7Bdrm, 27ppl, Sunsets, Pool, Theatre

Sunsets hit perfectly from the hilltop. The Casa Villa is our newest flagship, a 7-bedroom luxury villa perched above Mt. Irvine with sweeping Caribbean views, an infinity pool that spills toward the sea, and a private theatre & games room. Sleeps up to 27 across seven beautifully appointed bedrooms, built for family reunions, milestone birthdays, destination weddings & corporate retreats. Minutes from Mt. Irvine Beach, Stonehaven Bay & Pigeon Point. With a focus on large groups.

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Guest favourite

A modern villa is positioned along the coastline, featuring a saltwater pool adjacent to a spacious open area. The ocean can be seen in the background, while lounge chairs are arranged around the pool, creating an inviting outdoor space. Lush greenery surrounds the property.

Villa in Hope estates

4.95 out of 5 average rating, 43 reviews

"Malibu" in Tobago at the Ocean's Edge!

Think 'Malibu in Tobago' and you will know what it feels like to be welcomed into this luxurious penthouse villa at the ocean's edge. This stunning 3-bdrm villa located in Hope Estate, about a 10-min drive from the port in Scarborough, offers an unparalleled oceanfront experience with breathtaking views of the Atlantic and a salt water pool to make Malibu an even more enticing choice. All rooms are air-conditioned and minimally, yet beautifully, appointed with an ocean view.

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Top Guest favourite

A spacious living area is characterized by modern furnishings, featuring a navy blue sectional sofa with decorative pillows. A coffee table sits atop a woven area rug, and natural light floods the space through ceiling windows, illuminating the open layout that connects to the kitchen.

Villa in Crown Point

4.98 out of 5 average rating, 87 reviews

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

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Top Guest favourite

A modern dining area features a wooden table surrounded by six light-colored chairs. A decorative plant sits at the center of the table. A large framed image of a turtle swimming above coral decorates the wall, adding a coastal touch to the space.

Apartment in Buccoo

5.0 out of 5 average rating, 40 reviews

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

Comfort, convenience, and island charm await at Buccoolito 2B Enjoy this 2-bedroom, 2-bathroom modern condo with a fully equipped kitchen and a perfect view of the pool. Located in a secure, gated development with 24/7 security, Buccoolito 2B is just 15 minutes from both the airport and the ferry terminal. Centrally located, minutes away from the Picturesque Buccoo Beach and 15 minutes drive to the Popular Pigeon Point Beach and Store Bay Beach.

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Top Guest favourite

A private pool is surrounded by well-maintained greenery and decorative planters. The pool features a smooth edge with stairs leading into the water, and the bright blue surface reflects the sky above. A storage tank is positioned discreetly in the background.

Home in Bon Accord

4.96 out of 5 average rating, 136 reviews

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.

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Top Guest favourite

A bright living and dining area is featured, with large windows allowing natural light to fill the space. A comfortable gray sectional couch and a light-colored coffee table are positioned in front of a television. A dining table with chairs and artwork on the wall add to the inviting ambience.

Apartment in Black Rock

4.95 out of 5 average rating, 58 reviews

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.

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