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Holiday houses in Great Tobago

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Top-rated holiday rentals in Great Tobago

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Guest favourite
A scenic patio area features two lounge chairs positioned to face the ocean, surrounded by tropical plants in bright yellow pots. The view includes a vibrant turquoise bay and distant hills under a blue sky with scattered clouds.
Villa in Northside

Sailfish Villa Beachfront Magens Bay St. Thomas!

Private beachfront villa on world-famous Magens Bay Beach! 5BR/4.5BA oceanfront property with direct beach access. Features a 1BR/1BA beachfront cottage that sleeps up to 4 guests. Enjoy swimming with sea turtles, snorkeling, and kayaking just steps below the villa. Amenities include an outdoor shower, clear kayak, paddle boards, and stairs to the water. Located in the private neighborhood of Peterborg, just a short shoreline stroll to Magens Bay Beach. Property is equipped with a Generator.

FamilyLocationCheck-in

4.91 out of 5 average rating, 139 reviews
Top Guest favourite
A private infinity pool is situated on a terrace, overlooking lush greenery and a panoramic ocean view. A vibrant rainbow arcs across the horizon, while gentle waves suggest a tranquil atmosphere. The pool's edge blends seamlessly with the surrounding landscape.
Guesthouse in Saint Thomas

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 21 or older.

LocationValueNearby

5.0 out of 5 average rating, 118 reviews
Top Guest favourite
The spacious living area features high vaulted ceilings, with ample natural light from large windows. A long dining table accommodates multiple guests, while a cozy seating area is arranged for relaxation. A decorative bookshelf filled with various books extends along one wall, enhancing the inviting atmosphere.
Villa in Charlotte Amalie

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Private gated parking and a cafe and art gallery right downstairs.

FamilyValueOutdoor spaces

4.99 out of 5 average rating, 158 reviews
Guest favourite
A modern living area features a comfortable seating arrangement with a dark sectional sofa and light accent chairs. Natural light filters through large windows, highlighting the room's stylish decor, including a unique chandelier and a tasteful area rug, all with views of the harbor.
Apartment in Charlotte Amalie

Stylish & Luminous 2BR-spectacular water views!

Welcome to a newly renovated 1,800 sq foot 2 bedroom located in the heart of historic Charlotte Amalie! Our space is perfect for travelers who wish to experience the beauty of the US Virgin Island. Each room is oversized, with tall ceilings, and boasts stunning panoramic views of the Caribbean that are sure to take your breath away. The space is as stylish as it is comfortable, with modern furnishings and luxurious touches throughout, yet contextually appropriate for the historic setting.

FamilyValueView

4.95 out of 5 average rating, 152 reviews
Top Guest favourite
A modern living area features a large flat-screen TV mounted above a stylish wooden media console. A light-colored sofa and accent chairs are arranged around a circular coffee table, with large windows offering views of the ocean and islands beyond. Natural light fills the space.
Condo in East End

5 Star NEW Luxury Fully Remodeled 1x2 Pool & Beach

NEW! Spacious 1 Bedroom/2 Bathroom 1200 sq foot -2024 FULLY REMODELED OCEANFRONT Villa in St. Thomas, VI. This spacious villa has an all-new modern interior, spacious separate bedroom, 2 bathrooms, a private balcony and all the amenities! Situated on the sought-after East End, this luxurious retreat offers sweeping ocean/island views. Designed with modern elegance and spacious comfort in mind, the villa provides direct access to three pools, two gourmet restaurants, and a private beach.

LocationValuePool

5.0 out of 5 average rating, 64 reviews
Top Guest favourite
Villa in Anna's Retreat

Good Vibes Only Ocean Villa-Views/Pool/Sundeck/Fun

Gorgeous Caribbean paradise w/ a salt water pool. Sleeping for 10 including 3 private bedrooms w/ensuite bathrooms. Sprawling living & fully stocked kitchen. Additional Queen sleepers in living & master + 1/2 bath. Enjoy stunning ocean views w/ direct line of site over to White Bay in the BVI, Tortola, Hans Lollik & Mandahl Beach/Salt Pond. The villa is equipped w/multiple patio areas & stunning pool w/ soothing trade-winds that blow through the property for comfortable outdoor living.

LocationValueBarbecue

4.98 out of 5 average rating, 100 reviews
Top Guest favourite
A wooden bench with a sign reading 'SAIL AWAY' is positioned on a patio, overlooking the vibrant blue waters of a beach. Lush green foliage and palm trees frame the view, with rolling hills visible in the distance under a partly cloudy sky.
Condo in East End

Sail Away II-WOW Beachfront to Paradise Remodeled

Full property generator. Sail Away II at Sapphire Beach Resort and Marina is located on the beachfront just steps away from the sparkling Sapphire Beach. The patio leads you to a dazzling infinity pool and the option of 2 immaculate beaches. Caribbean water and amenities galore await you. No need to leave the tranquility of your room thanks to the many home furnishings within your vacation paradise. Beach level, beachfront & lush surroundings is yours to escape the hub of city life.

FamilyLocationAccess

4.95 out of 5 average rating, 144 reviews
Top Guest favourite
A serene beach scene captures clear turquoise waters gently lapping against the shore. Lush greenery cliffs rise in the background, adding natural beauty to the landscape. A small boat and a few swimmers can be seen enjoying the calm sea, enhancing the tranquil atmosphere.
Home in East End

Private Pool in Paradise! Ocean View Steps 2 Beach

Come enjoy the island life at this tranquil villa with private pool...only steps from the beach! Cooler, snorkeling gear, and beach chairs INCLUDED! The entire home has been remodeled. The pool has been fully updated as well as the deck area, which includes brand new furniture and high-end loungers. A new gas grill has also been added for your outdoor grilling pleasure. Stream all your favorites with our strong Wi-Fi. Upscale restaurant, Pangea, is just steps away. Free parking.

LocationValueView

4.97 out of 5 average rating, 157 reviews
Top Guest favourite
An aerial view of a contemporary home reveals a red roof and an infinity pool lined with lounge chairs. Surrounding greenery enhances the sense of privacy, while a spacious driveway provides easy access. Large windows allow for plenty of natural light to enter the interior.
Villa in Charlotte Amalie

Hilltop Paradise Vacation Package with Jeep

Start your next adventure and step into this brand new contemporary modern home hidden in the hills of St. Thomas. Here, you will be greeted with incredible, breathtaking views and an infinity pool overlooking the beautiful Charlotte Amalie. This carefully designed retreat sets the tone for a perfect adventure getaway for a group of friends/couples, or the perfect relaxation stop for a family. Whatever you choose, this home will not disappoint.

LocationFamilyCheck-in

4.99 out of 5 average rating, 104 reviews
Top Guest favourite
A bright living area features large windows that frame scenic mountain views. A light-colored sofa and two armchairs surround a wooden coffee table, complemented by a natural stone accent wall. Decorative plants add a touch of greenery, while a television is mounted on the wall.
Apartment in Cruz Bay

Esperance~Pool~New~National Park

Spacious 2BR, 2BA luxury apartment in Fish Bay Skytop with full kitchen and washer/dryer. Both bedrooms feature Loom & Leaf memory foam mattresses. King bedroom with en-suite bath, second bedroom with queen bed and bathroom across the hallway. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay dining, shopping, groceries, 25 min to North Shore beaches. 4 ft shared pool and BBQ with two other apartments.

ValueLocationHiking

5.0 out of 5 average rating, 126 reviews
Top Guest favourite
A covered deck presents a large wooden dining table surrounded by mismatched chairs, offering panoramic views of the turquoise waters and nearby islands. The serene atmosphere is complemented by soft clouds drifting overhead and the expansive horizon.
Home in Wesley Will

Stylish, Secluded, Hot Tub and Amazing Views

Nestled on top of Cooten Bay in Tortola, British Virgin Islands, Cooten House has amazing views that will take your breath away. Whether you are looking for a romantic getaway, a place to relax and soak up the sun or all of that plus close proximity to great surfing spots, Cooten House will exceed your expectations.

FamilyLocationLong stay

4.95 out of 5 average rating, 168 reviews
Top Guest favourite
A person stands on a balcony, looking out over a vibrant turquoise ocean, framed by lush greenery. The rolling hills in the background fade into distant mountains under a clear blue sky, enhancing the serene view.
Villa in White Bay

Ocean View Villas, 1 Bedroom- (Seascape)

The villa had an AMAZING view, is updated and extremely comfortable. The breeze is amazing, kitchen fully prepared for use, impeccably clean every where, beds so comfortable, views to die for-sunrises over Great Harbor and sunsets over White Bay, spacious inside and out.

LocationHospitalityNearby

4.96 out of 5 average rating, 24 reviews

Popular amenities for Great Tobago holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Great Tobago

Top Guest favourite
The image captures an aerial view of the property, highlighting a private infinity pool adjacent to a wooden deck. Two cushioned lounge chairs face the ocean, overlooking rocky shores and calm turquoise waters. Lush greenery surrounds the area, enhancing the tropical environment.
Home in Great Harbour

Tranquil Desires, Villa

LocationFamilyPool

5.0 out of 5 average rating, 22 reviews
Superhost
Apartment in Saint Thomas

The Grande Escape in Yacht Haven Grand

LocationNearbyAir conditioning

5.0 out of 5 average rating, 4 reviews
Top Guest favourite
The modern villa is prominently positioned on a hillside, featuring a spacious terrace and an inviting pool. Large glass doors enhance the seamless connection between indoor and outdoor areas. Lush greenery surrounds the property, adding to its serene environment.
Villa in Road Town

Luxurious 4 bed with pool and spectacular views

ValueFamilyIndoor spaces

5.0 out of 5 average rating, 34 reviews
Top Guest favourite
An outdoor area features a private pool surrounded by a deck with lounge chairs. Lush greenery and rocky landscaping create a natural setting, while the two-story house offers large glass windows that showcase scenic views of the hillside.
Villa in Wesley Will

Villa Naku, escape and relax.

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 69 reviews
Top Guest favourite
A private saltwater pool surrounded by a spacious deck offers stunning views of the turquoise waters and lush hills. Beach lounge chairs are present for relaxation, accompanied by vibrant potted plants, enhancing the serene outdoor space.
Home in Coral Bay

Seascape Villa w/ Private Pool & Spectacular Views

ValueFamilyKitchen

5.0 out of 5 average rating, 24 reviews
Top Guest favourite
Home in Coral Bay

Panoramic Ocean views and off Grid

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 11 reviews
Top Guest favourite
A villa with a light-colored exterior and distinct green roofs is set against a backdrop of ocean views. A staircase leads down to a courtyard featuring a pool, surrounded by tropical plants and outdoor seating areas, creating a welcoming and spacious atmosphere.
Home in West End

Villa Rosa

LocationFamilyQuiet

5.0 out of 5 average rating, 32 reviews
Top Guest favourite
An infinity pool featuring a turquoise hue creates a seamless connection with the surrounding ocean views. The vibrant colors of the villa are complemented by the lush landscape. A covered terrace with dining furniture is visible, offering a relaxed outdoor space.
Villa

Stunning Limeberry Villa, a designer's dream.

ValueLocationPets

4.98 out of 5 average rating, 59 reviews