Places to stay near Pirate's Bay

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Top-rated vacation rentals near Pirate's Bay

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Superhost
A comfortable rattan chair is positioned on a glass-enclosed veranda, offering unobstructed views of the ocean and distant hills. Brightly patterned cushions add a touch of color, while the surrounding greenery enhances the natural ambiance of the space.
Home in Charlotteville
4.85 out of 5 average rating, 48 reviews

Chachalaca Villa | Eco Lovers Rain Forest Getaway

Thoughtfully updated 3 bedroom villa perched on Flagstaff Hill with stunning views of Man-O-War bay. We are located in the rain forest of Eastern Tobago. Perfect for nature lovers and divers. A few minutes drive down the hill leads right to the beach. Updates include new stainless steel appliances, new beds & linens, smart TV Wifi speakers, lighting fixtures, etc. The amenities you’d expect in the city, in the rain forest. However, you’ll find it hard to leave the veranda’s breathtaking view.

Superhost
A colorful hammock is suspended between posts on a wooden deck, inviting relaxation. The deck offers expansive views of the Caribbean Sea and surrounding greenery, with distant islands visible on the horizon. A wooden chair is positioned nearby, enhancing the comfortable outdoor setting.
Villa in Bloody Bay
4.8 out of 5 average rating, 106 reviews

Auchenbago rustic luxury, stunning panoramic views

Relax and catch the breezes and spectacular views of the Caribbean Sea at a rustic villa offering total privacy and comfort. Marvel at the nearby turtles' nesting grounds and, weather permitting, take paths along the 4.5 acre landscaped property to the sandy beach and waterfalls below. Relax with a book from our library, perhaps in one of the Mexican hammocks on the villa's wraparound deck. Prepare meals in the well-equipped kitchen and enjoy leisurely dining in the screened-in dining room.

Top guest favorite
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, 177 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.

Superhost
An outdoor seating area features a round stone table surrounded by white benches, illuminated by string lights. A hammock is suspended nearby, and lush tropical plants frame the space, creating a relaxing atmosphere in the evening light.
Cottage in Castara
4.86 out of 5 average rating, 101 reviews

Little Houses Tobago - Castara Cozy Cottage

Castara Cozy Cottage features 2 bedrooms, a bathroom, a kitchen, and a living room. A front balcony provides a relaxing spot to enjoy the lush gardens, ideal for bird watching, as well as views down the valley and of the stars at night. The cottage, over 30 years old, offers cozy yet comfortable accommodations for travelers, making it a perfect escape. Castara is situated on the northern coast of the island. Although it is 40 minutes away from the capital, Castara is centrally located.

Top guest favorite
A spacious bed is dressed with crisp white linens, complemented by colorful decorative pillows featuring floral patterns. A soft lamp with an intricate base sits beside the bed, and gentle light filters through the light-colored curtains.
Apartment in Moriah
4.97 out of 5 average rating, 59 reviews

HOUSE IN THE MOUNTAIN! APARTMENT 2

A home away from home.....that comfortable relaxed feeling. Wake up to fresh air, and the sound of Tobago birds, including the Cocorico. Feel like listening to music......there is a Bluetooth speaker available! Feel like television......Direct TV is available! Feel like swimming and lounging - check out our pool and our floating breakfast - or - the beaches are not far away. Feel for entertainment....you can book our preferred entertainer! ....SAXOPHONIST....RICARDO SEALES!!!!!!

Superhost
A shaded pool area features a spacious in-ground pool with calm blue waters, accented by a rock feature. Two lounge chairs are positioned beside the pool, while panoramic sea views and lush greenery surround the space, creating a serene outdoor environment.
Home in Castara
4.78 out of 5 average rating, 36 reviews

The Wood House

The Wood House is a beautiful, secluded, open-plan cottage with spectacular sea views, a natural setting in a reclaimed woodland, and close proximity to Englishman’s Bay (considered one of the 10 most beautiful beaches in the Caribbean). The natural woodland attracts a large variety of wildlife making it ideal for birders or naturalists interested in exploring the Tobago environment. Walk the terraced grounds, explore Englishman's Bay estate, or just relax in the stunning views.

Guest favorite
The studio apartment features a spacious bed with decorative pillows, complemented by a couch and a kitchenette area. Natural light enters through glass doors leading to the outside patio, where views of the garden are visible. An inviting atmosphere is created by the light-colored walls.
Guest suite in Scarborough
4.92 out of 5 average rating, 155 reviews

Ocean view studio

Simple air-conditioned studio apartment with a private bathroom and an outside covered wood patio overlooking the Atlantic ocean. Refrigerator, microwave, teakettle, and toaster oven are located inside the studio. An outdoor counter with a single burner stovetop and sink for light breakfast and snacks. Absolutely no smoking inside the studio. Check-in after 1 pm For liability reasons, guests may not bring any visitors or any others to our home at any time, for any length of time.

Guest favorite
A wooden deck provides an expansive view of the Caribbean Sea and the lush, green hills of Charlotteville. The railing features a natural wood design, allowing for unobstructed scenery of the bay and coastline under a partly cloudy sky.
Cottage in Charlotteville
4.9 out of 5 average rating, 146 reviews

Bella Vista Cottage

Charlotteville (within the UNESCO biosphere reserve) is approximately 1.2hrs from the Tobago Airport, and off the beaten path. Bella Vista cottage overlooks the village, rainforest and Caribbean Sea. It is situated close enough to experience village life but tucked away to enjoy solitude and the most breath-taking views of the ocean, village, and rainforest! Beautiful beaches are just a 5-10 min walk away.

Guest favorite
The covered porch area features wooden lounge chairs, inviting relaxation. A backdrop of lush greenery and the tranquil bay is visible beyond the railing, where palm trees sway gently. The patio flooring is wooden, enhancing the natural ambiance.
Cabin in Parlatuvier
4.94 out of 5 average rating, 116 reviews

Tamarind House Villa Parlatuvier

Tamarind House Villa is situated on the leeward coast of Tobago in the beautiful fishing village of Parlatuvier. It is suitable for small groups, couples and families who enjoy a relaxed lifestyle away from commercial tourist areas. The villa overlooks the bay on one side and pristine tropical rainforest on the other. Guests will have sole occupancy of the house, pool and gardens.

Top guest favorite
The cabin features a rustic wooden exterior, surrounded by lush greenery. Wide, open windows provide a view of the outdoors, while a spacious deck includes chairs for relaxation. A red kayak is positioned on the ground, ready for use. The sky is clear and blue.
Cabin in Parlatuvier
4.93 out of 5 average rating, 68 reviews

Sugar Shack: beachfront Tobago cabin

Simple serenity on the seaside. Walk straight from your door onto the unspoiled beach of Parlatuvier. Located in the quaint fishing village, Sugar Shack cabin is your answer for the perfect getaway. Paddle away in our two-seater kayak, help “pull seine” with the local fishermen, or relax in the soft golden sand … spend your days away from tourists and experience real Tobago life.

Guest favorite
A large outdoor pool is surrounded by sun loungers positioned on a tiled patio. Lush vegetation and palm trees frame the scene, with a partially shaded area provided by the villa's roof. A clear blue sky is visible overhead.
Home in Castara
4.9 out of 5 average rating, 41 reviews

Beautiful villa nr Castara & beach

A stunning 5 bedroom villa near Castara and Englishman's Bay. For adventurous types, set in the rainforest and very private, with views down to the Caribbean Sea. Comes with pool, bar, outside seating, sitting room, study and kitchen. All bedrooms en-suite. Wireless internet. Full villa rentals only.

Superhost
The exterior of a two-story building is visible, featuring white walls with green accents. A wide staircase leads to a second-floor porch adorned with decorative railings. The structure is situated directly along a sandy beach, offering views of the surrounding landscape.
Apartment in Charlotteville
4.75 out of 5 average rating, 8 reviews

Charming beachfront 3 bedroom Colonial Suite

Built in 1937, just ten steps from the palm-studded, horseshoe-shaped Man of War Bay, the Colonial Suite Tobago beachfront accommodation welcomes you to experience Charlotteville then and now. You’ll be charmed by this adorable place to stay.

Popular amenities for vacation rentals near Pirate's Bay