Holiday houses in Orange Hill

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.

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!

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.

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.

"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.

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

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

Ocean-View Tobago Getaway Near Attractions

Relax and rejuvenate in this comfortable and serene space. Perched atop a hill in Prospect, Tobago, this tranquil retreat offers breathtaking ocean views, lush gardens, and tropical charm. Wake to birdsong and rustling leaves as you enjoy comfort and serenity surrounded by nature. Perfect for couples or families seeking peace with easy access to Tobago’s most popular beaches, attractions, and authentic island experiences. Close, yet far enough to truly unwind.

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.

Nirvana Tobago | Ocean View Villa + Saltwater Pool

Find your Nirvana in Tobago. This private Caribbean villa blends beautiful ocean views with relaxed indoor outdoor living, perfect for family vacations, friends' getaways and special celebrations. Unwind by the saltwater pool, enjoy cocktails at the poolside cabana bar, gather for alfresco dining or retreat to beautifully appointed ensuite bedrooms. A chef's kitchen, 12 foot ceilings and fast WiFi complete your private island escape.

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.