House holiday rentals in Diego Martin

Luxurious Oasis 3Br. Villa with Private Pool

Luxurious villa with private pool and beautifully sculpted gardens, offering privacy and relaxed elegance. The master bedroom and spacious living room both open directly onto the pool deck, perfect for seamless indoor-outdoor living. Fully air-conditioned, modern 3-bedroom home is exceptionally spacious and includes parking for up to four cars. Ideally located on Trinidad’s Gold Coast Minutes from The Falls Mall, supermarkets, pharmacy, and walking distance to Park & Trinidad Yacht Club.

Location · Family · Decor

Beautiful Villa near City & Beach

Enjoy this perfectly situated Modernised Villa in St. Anns, located just 2 mins from the Queens Park Savannah, Port of Spain; making it a prime vacation spot! This entirely modernised split level home boasts three bedrooms, open plan living and dining area, WiFi and 50" Smart TV which lends itself to good use either as a vacation or business trip. Plan an eventful time as this home is near all of your favourite places and activities while being in a peaceful fully gated and secured location!

Location · Family · Access

Toucan Cottage - Off-grid 2 bed 2.5 bath house

Escape to your perfect off-grid mountain getaway! This 2-bedroom, 2.5-bath house offers stunning ocean views and a perfect blend of luxury and sustainability. Enjoy bird watching from the deck area, and access to a beautiful beach via 4x4 vehicle or a scenic hike. Ideal for nature lovers and adventurers alike or families looking for a peaceful haven 4x4 or AWD vehicle is needed to access house OR vehicle can park by entrance gate and someone can be hired to take you down to house and back up

Location · Value · View

Entire Boutique Home | 6 BR Sleeps 20 | Savannah

Welcome to 103 Woodford, a rare find in the heart of historic Woodbrook. Enjoy an entire boutique home re-imagined for modern living. Rooted in the area’s gingerbread charm, this six-unit property combines timeless architectural touches with contemporary Caribbean design. Step inside to discover thoughtfully crafted interiors. Each unit features a full kitchen, en suite bedrooms with king or queen beds, dedicated workspaces and pull out sofas for extra guests. Some units include balconies.

Location · Hospitality · Checkout

Cosy Convenient Suite (Private entrance)

Welcome to your cozy home base in the heart of Woodbrook — ideal for solo travelers working remotely or staying a little longer. This fully equipped one-bedroom suite features a private entrance, queen bed, en-suite bathroom, smart TV, fast Wi-Fi, and a stocked kitchenette with all the basics. You’re just a short walk to: Ariapita Avenue’s restaurants, bars & nightlife. Supermarkets, malls & local shops. Safe, simple, and central — book your stay and enjoy the ease of Woodbrook living.

Value · Location · Getting around

Scenic 3BR/2BTH Flat- Spacious & Clean. Serene.

Enjoy a space that is all yours, with a room for everyone. Emerse yourself in the tranquility that this home provides as it over looks the scenic hills of Diego Martin. This modern 3 bedroom, 2 bathroom home is the clean, spacious and comfortable environment for the quiet getaway you have been looking for. Take full advantage of the conveinient access to the hub of entertainment and amenities located in the capital city. Book your stay and discover all that Millie's Air BnB has to offer.

Family · Location · Condition

Pierre Point: Hilltop retreat, breathtaking views!

30 mins from the Airport; 25 minutes from Maracas Beach; 10 mins from the capital, Port-of-Spain. Welcome to your peaceful retreat set above the surrounding area. The home is reached via a short, and for some, slightly steep incline that levels off at the top. You will be rewarded with enhanced privacy, refreshing breezes, and sweeping vistas! Whether you're planning a romantic escape, or a productive remote work stay, this space is designed to make you feel right at home.

Value · Family · Comfort

The Outskirts Inn

Welcome to our cozy nook, centrally-located just 5 minutes away from the Queen's Park Savannah and 10 minutes from Downtown Port of Spain. You'll be close enough to all amenities including supermarkets, restaurants and bars. If you're outdoorsy you won't be disappointed, as there are ample green spaces in the vicinity which can be explored on foot. The convenience of this location is complemented by the peacefulness. Transport is also readily available.

Value · Family · Checkout

Goodwood Skyline Manor

Escape to Goodwood Skyline Manor, your serene sanctuary above Port of Spain. This spacious hilltop retreat features a luxurious hot tub, a massive pool, and breathtaking panoramic views of the city. Perfect for relaxing or entertaining, the home offers peace, privacy, and plenty of room to unwind. Enjoy stunning sunsets, cool breezes, and total tranquility in this quiet, exclusive getaway.

Family · Value · Nearby

Luxury Westmoorings Family Villa with Pool

Enjoy a spacious Westmoorings home with a private pool in one of Trinidad’s most convenient and sought-after areas. Ideal for families, groups, and business travellers, the home offers comfort, privacy, secure parking, and easy access to Westmall, restaurants, supermarkets, pharmacies, beaches, Chaguaramas, and Port of Spain. Professionally managed by WhiteRock for a smooth, reliable stay.

Location · Family · Indoor spaces

Robinson Villa, Santa Rosa

Are you looking for a quiet and secure location within the city of POS. Look no further our Robinson Villa is a modern 1 br Apt. located within walking distance to the city of Carnival. This home away from home provide you with all the conveniences you are accustomed to. Relax with the whole family at this peaceful place to stay.

Modern 3BR Getaway in St. James

Welcome to your home away from home in St James, Port of Spain. This unique listing offers exclusive access to two stylish, self-contained units on the same secure property, making it ideal for families, friend groups, or business travellers seeking comfort, flexibility, and privacy - all in one booking.

Location · Hospitality · Walkability