Holiday rentals with a patio in Plymouth

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.

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

We Casa - simple Tobago luxury

Welcome to WE CASA - a well-designed, three-bedroom villa with simple, stylish touches to make our guests feel right at home. The bright, open-plan kitchen, living room and dining room lead right onto the poolside patio so everyone can enjoy each other's company. When you're ready to have some quiet time, retreat to your snug, air-conditioned bedroom for an afternoon siesta or a good night's rest. The villa is centrally located from shopping, beaches, banks etc - nothing's too far in Tobago!

Poui Place - 4 Bd villa in Samaan Grove, Tobago

Escape to a private oasis at this exquisite 4-bedroom villa, nestled in a serene and exclusive location. Designed for those seeking the perfect blend of luxury and relaxation, this villa offers spacious living areas, premium amenities and modern décor with an abundance of natural light. The highlight of the villa is the sparkling outdoor pool, complete with a floating pavilion ideal for al fresco dining. Families will especially appreciate the wading pool, perfect for the little ones.

"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.

Plymouth View Villa: 2br & Pool

Bring the whole family to this great place with lots of room for fun. Our lovely villa in the serene paradise of Tobago is the perfect retreat! It offers a peaceful location where you can relax and unwind with your loved ones. One of the highlights of our villa is the wrap balcony, offering glimpses of the ocean in the distance. It's the perfect spot to savor your morning coffee or enjoy an evening cocktail while witnessing breathtaking sunsets that will leave you in awe.

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 Escalante TBGO Lower Level

Lower Level. If you’re searching for an experience then this is your destination!! Villa Escalante is a modern architect designed gem, nestled in the Main Ridge Forest. The Villa is designed to capture the view of Englishman’s Bay and the Main Ridge, a perfect spot for viewing both the flora and fauna. The Main Ridge Forest is a designated UNESCO biosphere reserve. The architect designed the villa so that nearly every living space has a 180-degree view.

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.

Classic Beachfront Living, Villa 1 of 6

Secluded and peaceful villa surrounded by lush cedar trees with views of Stonehaven Bay. Features 3 en-suite bedrooms, spacious verandahs, and fully equipped kitchen — perfect for families or small groups seeking tranquility steps from the beach. All guests enjoy access to the beachfront pool, bar, and beach, plus resort-style amenities, daily cleaning, and in-villa chef service.