Holiday rentals with a pool in Black Rock

Stylish Getaway Near Beaches. Quiet. Pool. Jacuzzi

Enjoy comfort and privacy in this spacious, modern apartment set in a quiet, safe community close to beaches, dining and nightlife. Perfect for professionals or couples, the space features a queen-size bed, cozy living area with Smart TV, fast Wi-Fi, fully equipped kitchen, large bathroom with massage shower, hot water, and private balcony. Guests also enjoy access to a swimming pool and jacuzzi—ideal for relaxing after work or a day out. We look forward to helping you make your visit memorable.

Value · Location · Air conditioning

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.

Family · Value · Indoor spaces

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.

Location · Family · Indoor spaces

Sea View Villa Cluster 63A(2BR,Pool,Wifi,Golf)

Sea front villa with scenic entrance near the Magdalena Hotel with an international Golf Course. Minutes away from iconic beaches and shopping malls. Furnished, 2 bedrooms with upgraded ensuite bathrooms, open concept, and a private pool with sundeck on the ground floor of the duplex. Gated community(manned 24 hours) Fully air-conditioned along with ceiling fans & Netflix. Contains outside bathroom and utility room. * Maid service available at an additional charge.(Mandatory after 3nights)

Location · Value · Air conditioning

Joie de Vivre - a bright and airy holiday retreat

With a large open plan kitchen, living room, dining room with folding doors that lead to a spacious pool deck, Joie de Vivre is the perfect villa for a group holiday or as we say in Trinbago 'ah bess lime'. The expansive pool is truly inviting and you're going to find it hard to be anywhere else but in and around it! There are 5 air conditioned bedrooms, 3 with access to the upstairs verandah and views of our famous Buccoo Reef. Grab your morning coffee, sit outside and just take it all in.

Value · Family · Condition

Nirvana Tobago Villa Saltwater Pool & Ocean View

Nirvana Tobago is a luxurious Private Villa on the Caribbean coast with Ocean Views. Ample alfresco dining space, poolside cabana bar and saltwater pool. Over 4000+ sq. ft residence is graced with 12-foot ceilings and skylights. Interiors feature a chef kitchen and well-appointed bedrooms with ensuite bathrooms, no better place to restore your sense of bliss! Perfect for weekend getaways, extended stays and remote working. We have fast and reliable wifi and laptop friendly workspaces.

Family · Value · Walkability

Stylish 2BR Condo w/ Pool Near Buccoo Beach

Welcome to The Cocoa Condo. A unique two-bedroom condominium, located on the gated compound of the newly constructed Buccoo Homes Phase 2. This unit is mere meters from the Buccoo Food Court and a 15-minute walk to explore the renowned Buccoo family-friendly beach, the protected Buccoo Reef, and the shallow, crystal-clear "Nylon Pool". Popular activities include glass-bottom boat tours, horseback riding in the ocean, and the lively Sunday School goat and crab races.

Location · Value · Cleanliness

Condo on the BEACH

This apartment is horizontal with the house as it is frontier towards the beach. The verandah has a top tier view of the ocean and pool. Entering into the living room and kitchen which is more of the garden view. The bed room have a beautiful view over looking the infinity pool and the ocean back drop. The apartment consists of dual colors to create a clam and peaceful ambience as to keep a cool comfort feeling. Please note the pools is shared with two other units.

Location · Family · Amenities

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

Value · Location · Comfort

"Hibiscus" with the Caribbean Sea on its Doorstep!

This classic beach-front villa is located along the Grafton-Turtle Beach coastline, with a sheltered inlet for sea-bathing literally on the doorstep. At Hibiscus you’ll enjoy stunning ocean and sunset views, easy beach access, waking up to the sound of the waves, a well-maintained tropical garden, long walks on the beach, tidepools great for exploring or snorkelling on your doorstep and so much more. Paradise awaits!

Family · Location · 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.

Family · Location · Kitchen

Classic Beachfront Living, Villa 6 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.

Family · Location · Beach