Holiday rentals in Scarborough

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Top-rated holiday rentals in Scarborough

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The interior space features a wooden four-poster bed, draped with soft curtains. A round table surrounded by chairs is positioned nearby. Natural light floods the area, highlighting the light-colored walls and polished floor. A cozy rug adds texture, complementing the rustic furnishings.
Villa in Bacolet
4.89 out of 5 average rating, 110 reviews

Bago Beach House: Oceanfront

This spacious villa offers 3 bedrooms, 3 baths, living room, dining room, private patios and a rooftop terrace. The interior rooms were designed with high ceilings to enhance the openness and comfort of the house. Listen to the waves crash on the shore as the sea breeze lulls you to sleep. Enjoy all nature has to offer with the panoramic views of the ocean, hills, sunrise and sunsets. Kick back and enjoy quality time with family and friends. Make lasting memories! Also view: Bago Beach Villa.

Top guest favourite
Apartment in Buccoo
5 out of 5 average rating, 19 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.

Guest favourite
The villa's exterior showcases a modern design with white walls and elegant columns. Flowering plants, including red blossoms, frame the entrance, enhancing the welcoming ambiance. The balcony features decorative ironwork, and soft lighting illuminates the facade against a twilight sky.
Flat in Lowlands
4.95 out of 5 average rating, 82 reviews

El Romeo, Casa Josepha | 10min Drive to Beaches!

Welcome to Casa Josepha, our bright, exquisite, new villa, featuring our romantic lux apartment- El Romeo. Wake up to tropical bird songs in our lush gardens. Enjoy the bright living and kitchen areas, retreat to your work space or siesta in your cozy bedroom. Only 12 minutes from the airport, a 5-12 minute drive to beaches, snorkeling, diving, biking, hiking, Buccoo reef, horseback riding, golf, and spas. Walk 2-16 minutes to restaurants, bakery, grocery, bar, mall, shopping & a movie theatre!

Superhost
A comfortable living area features two gray sofas adorned with patterned throw pillows, positioned across from a light wooden coffee table. A decorative vase sits on the table, and a subtle area rug completes the space. A door and artwork are visible in the background.
Guest house in Scarborough
4.9 out of 5 average rating, 21 reviews

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.

Guest favourite
Flat in Castara
4.79 out of 5 average rating, 14 reviews

SunsetView- Castara Roundhouse

Self-Catering SunsetView is an entire 2-bed 2-bath upper-floor apartment at Castara Roundhouse with a spectacular 200° wraparound balcony overlooking the sea, village, and rainforest. There’s an open-plan living room and kitchen with wooden shutters that open fully onto the balcony. Both bedrooms have ensuite bathrooms, and the space is naturally cooled by ocean breezes, finished in natural wood and concrete for relaxed Caribbean luxury and unforgettable sunsets. 55" TV -Prime/Netflix & Chill

Guest favourite
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
4.93 out of 5 average rating, 162 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.

Superhost
The exterior of the historic cottage displays a combination of wooden shingles and large windows. A sloped metal roof shelters the structure, while lush greenery and flowering plants frame the entrance, inviting guests to explore the charming architecture.
Cottage in Scarborough
4.8 out of 5 average rating, 66 reviews

The Fort Cottage

Welcome to our charming, historic home in this old Tobago neighborhood. The property was recently renovated, and all modern conveniences were installed but it maintains all the charm of its 150-year history. There’s almost always something in season - sapodilla, mangoes, lemons or guavas. Guests are welcome to fruits but are reminded that the chickens and iguanas are pets, not food. A short stroll away is the magnificent views of Fort King George built in the late 18th century.

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
4.94 out of 5 average rating, 36 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.

Top guest favourite
Home in Scarborough
5 out of 5 average rating, 23 reviews

Blanket & Brew- Private and Cozy 2 Bedroom

Welcome to Blanket & Brew! This private home is tucked away in Bacolet, Tobago, and was designed for dreamers, readers, and anyone craving a little peace. Inside, you’ll find: • Plush blankets and throws for ultimate snuggling • A self-serve coffee and tea station. • Ambient lighting, calming décor, and the scent of vanilla or cedarwood in the air • A few books and games to enjoy. Outside, enjoy: • A private patio to enjoy morning brews with sunrise or sunset views

Guest favourite
Flat in Scarborough
4.93 out of 5 average rating, 14 reviews

Romantic Suite + Spa Tub | Convenient Location

Nuvana is nestled in the heart of Scarborough, Tobago, offering free parking. No need to drive – it’s just a short walk to the ferry port KFC Subway Royal Castle and supermarkets. Relax in the living room with a 70” TV or the bedroom with a 55” TV. Netflix Tubi and Hulu are all available for binge-watching. Finally, unwind in our spacious bathtub with complimentary bath salts to soothe your body aches.

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.
Flat in Black Rock
4.96 out of 5 average rating, 49 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.

Superhost
A modern kitchen is configured with light green cabinetry and stainless steel appliances. A unique artwork decorates the wall, while a small dining area features two bar stools at a sleek counter. Natural light enters through a window covered with blinds.
Cottage in Carnbee
4.79 out of 5 average rating, 47 reviews

Majestic Suites Cottage

This unique place has a style all its own. A Modern cottage nestled in the western end of the island. 6 minutes away from the nearest beach, 4 minutes away from the largest supermarket on the island and 7 minutes away from the largest mall. We also provide rental vehicles as well.

Popular amenities for Scarborough holiday rentals

When is the best time to visit Scarborough?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Scarborough?

    Scarborough has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in guesthouse rentals in Scarborough?

    Experience the best of Scarborough with our guesthouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Scarborough?

    Four-legged friends are welcome in Scarborough. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Scarborough?

    Yes! Work meets play with ease at over 30 vacation rentals in Scarborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Scarborough vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Scarborough, available on Airbnb. Make a splash and soak up the sun in style!

  • Do villa rentals in Scarborough have air conditioning?

    Absolutely! We offer over 10 villa rentals with air conditioning in Scarborough. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Scarborough have a kitchen?

    Absolutely! We offer over 30 apartment rentals with a kitchen in Scarborough. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Scarborough have wifi?

    Absolutely! We offer over 40 apartment rentals with wifi in Scarborough. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Scarborough have free parking?

    Absolutely! We offer over 10 villa rentals with free parking in Scarborough. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Guesthouse Rentals in Scarborough?

    Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Scarborough

  • Total holiday rentals

    Explore 100 holiday rentals in Scarborough

  • Nightly prices starting at

    Scarborough holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    100 of Scarborough holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Scarborough rentals

  • 4.7 Average rating

    Scarborough stays receive an average rating of 4.7 out of 5 from guests