Holiday rentals with a patio in Black Rock

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

Saltwater Pool, Lush Garden, 5-10 min walk Beaches

Arcadian Bliss is a 4 bedroom, 3.5 bathroom, U-shaped home set in a beautiful, sloping one-acre garden. This fully-airconditioned villa features a 30ft x 15ft saltwater pool, a pickleball court and is 5 mins walk to Back Bay with its long stunning beach, rocky outcrops and "salt pools". 10 mins walk takes you to Mt Irvine Beach with its snorkelling, swimming, kayaking, surfing, and beach bar. Also 10 min walk away are a few restaurants, bars, fruit stand, fish stall, and mini mart.

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

Bahari Blu Tobago Saltwater pool? Beach or both?

Offering 25% weekly (book for 7 days or more) discount rates from $350 USD. Built on an elevation that delivers unimaginable sunsets with astounding afterglows. Affordable space for a family or group of friends who would like to share an artsy vacation home. Reconnect. Celebrate life together. Home is open concept with cathedral ceilings, a well equipped kitchen and a saltwater pool. Comfy beds, luxurious linen. Dbl occupancy 8 guests. Single bed on request

Island breeze penthouse

Forget your worries in this elegant, beautiful and relaxing space. Our penthouse is located at Building 9, Apartment 4D. Sip your coffee in our balcony while enjoying the morning island breeze and a view of the pool. Enjoy great food at the Food Court, which is located directly in front of our compound. No need to cook😉 Unfortunately, we do not allow children below the age of 10 due to safety concerns in the balcony, as we are on the 4th floor.

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.

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.