Smoking friendly holiday rentals in Trinidad and Tobago

Cozy, 1 Room Tiny Home Retreat, Woodbrook, T'Dad

Jay's Place A self contained 1 bedroom unit suitable for a lone traveller or up to 2 persons it's a stone's throw from Embassies and all must-see options in the heart of Woodbrook. Whether you're in town for business or to explore, this "Tiny Home" is perfect for you. Delight in the variety of Cafes, Restaurants, Bars, Street Food and entertainment calling to you. Private entrance, high speed internet, comfortable full size bed, kitchen, small patio area, with Street PArking for your vehicle.

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.

SuiteDreams- Modern Condo Piarco | Pool & Gym

Welcome to SuiteDreams; a stylish 2-bedroom, 2-bathroom condo safely nestled within a gated community in the prime area of Piarco, Trinidad. It's just 5 minutes from the Piarco International Airport. Perfect for travelers or staycations, it features modern décor, a fully equipped kitchen, and access to a shared pool and gym. Conveniently located near to malls, groceries, gas stations, banks, restaurants and nightlife. SuiteDreams offers comfort, charm, and convenience for short or long stays.

Graceful 1BR Suite • Cozy • Safe • Relaxation

✨ About This Space✨ Step into your private city-view retreat at One Woodbrook Place — in the heart of the Capital, Port of Spain. Ideal for business travellers, consultants, couples, and extended-stay guests, this 1-bedroom, 1-bath condo blends comfort, peace of mind, security, and a prime location. Enjoy calming balcony views, Wi-Fi, modern amenities, and 24/7 secure parking — just moments from dining, nightlife, cultural events, and Ariapita Avenue. Your home away from home awaits.

Divine Source 1: Entire Apt + Free Airport Shuttle

More than a stay—enjoy an authentic Trinidad experience with Free airport transfers, local food, island tours, and personal guidance. Hosts up to 10 guests 5 mins from Piarco Airport. Features 3 bedrooms (2 with AC) with queen, double, bunk beds, and a futon. Includes 24/7 self-check-in & fast Wi-Fi. Tours from $65 USD (1–2 guests), optional taxi, and meals. Walk to transit and eateries; easy access to Port of Spain. Perfect for layovers, families, large groups, and business.

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

The Relaxant

In gated community close toi airport, Opposite is a Domino's Pizza and Wendy's and the entrance to plaza which contains a casino, supermarket, severals restaurants, a pub, bank etc Within 500 feet is a gas station, KFC, prestomarket for breakfast and bakery needs and The CR highway which goes direct to Port of Spain. One can stay here without a vehicle. If on foot, one can get a taxi in front the community to Arima Central and from there to POS

Alibaba’s Sea Breeze Apartments

Entspann dich in dieser besonderen und ruhigen Unterkunft. Direkt am Strand von Castara‘a Little Bay gelegen mit Blick auf das Riff und die gesamte Bucht. Alles im Dorf fussläufig erreichbar. Durchdacht eingerichtete Studios mit großem Doppelbett, Moskitonetz und Deckenventilator, eigenem Bad, Küche und Balkon. Naturnaher Urlaub in einem Fischerdorf it einheimischen Restaurants und einem kleinen Supermarkt. Alles was man zum Entschleunigen braucht!

The Loft at Sallas Getaway

🌿 Experience the Charm of SALLAS Getaway – Romance, Nature & Memorable Moments Perched in the peaceful hills of Gran Couva, SALLAS Getaway is more than just a place to stay—it’s an escape into nature, romance, and togetherness. Whether you’re searching for a quiet retreat for two, a unique venue for life’s milestones, or an inspiring space for a corporate recharge, SALLAS offers the perfect blend of rustic charm and modern comfort. ✨

Playa del Maya Luxury 4-BR Beachfront Villa, Unit 1

Welcome to Playa del Maya – four luxury beachfront villas nestled within a secure & private gated agricultural estate. Ideal for travelers seeking an escape from crowded beaches, hotels, and the hustle of typical tourist destinations, each villa offers a seamless blend of refined luxury, tropical tranquility, and panoramic views of the North Atlantic Ocean. Currently, two villas are available for short- or long-term stays through Airbnb.

Jungle loft in the heights of Aripo

Deep into Trinidad's northern range on our little agricultural set up is the Jungle Loft. Exactly on the trailhead for the three main oilbird caves in Aripo - and the island's largest cave system, there are easy walks along the road into the rainforest. Due to the length and varying conditions of the road we’re best suited to guests looking to explore the area or looking for a retreat or if you just really love the place!

Safe and Cozy Carnival Spot!

Enjoy a stylish experience at this centrally-located 1 bedroom apartment in a gated compound with pull out couch for extra room. Fully Air-Conditioned, Fully Furnished, WiFi, Cable, Netflix, parking for 1 and private patio!