Smoking-friendly holiday rentals in Scarborough

4.83 out of 5 average rating, 6 reviews

A dining area features a large marble table surrounded by high-backed chairs in various colors. A striking artwork of a sea turtle swimming in a tropical setting is displayed on the wall above the table, adding a touch of coastal charm.

Townhouse in Crown Point

Crusoe Escape Villa - Smart Home

Crusoe Escape Villa- Fully Smart Home Modern Amenities: Enjoy high-speed Wi-Fi, air conditioning throughout, a 75" flat-screen TV with streaming services, a Playstation 5 game console and a surround sound system to make your stay comfortable and enjoyable. Don’t lift a finger! Proximity to Attractions: Located just a 4-minute drive from the airport, with pristine beaches, renowned dive sites, and charming local restaurants, our villa offers convenient access to the best that Tobago has to offer

Top Guest favourite

An infinity pool glistens under a bright blue sky, with clouds casting soft shadows. Comfortable lounge chairs with umbrellas line the poolside, surrounded by lush greenery. The structure of the villa features large windows and a wooden overhang, blending seamlessly with the natural environment.

Apartment in Bethel

4.99 out of 5 average rating, 136 reviews

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.

4.75 out of 5 average rating, 12 reviews

A comfortable bedroom features a spacious bed with neutral bedding, complemented by a bedside lamp illuminating the space. An air-conditioning unit and a window with blackout shades maintain a cozy ambiance. A wooden folding rack is visible for additional storage, enhancing practicality.

Home in Scarborough

Little House by the Fort, Enchanting Tobago Escape

Nestled just 3 minutes from Scarborough, Little House by the Fort offers a serene residential atmosphere with the convenience of nearby supermarkets, healthcare, entertainment, beaches, restaurants, and more. Located steps from the historic 18th-century Fort King George ruins and the Tobago Museum, guests can enjoy morning strolls with stunning views and refreshing breeze. Whether you’re here for relaxation or adventure, our home provides the perfect base for an enchanting Tobago escape.

Top Guest favourite

A spacious bed is dressed with crisp white linens, complemented by colorful decorative pillows featuring floral patterns. A soft lamp with an intricate base sits beside the bed, and gentle light filters through the light-colored curtains.

Apartment in Moriah

4.97 out of 5 average rating, 59 reviews

HOUSE IN THE MOUNTAIN! APARTMENT 2

A home away from home.....that comfortable relaxed feeling. Wake up to fresh air, and the sound of Tobago birds, including the Cocorico. Feel like listening to music......there is a Bluetooth speaker available! Feel like television......Direct TV is available! Feel like swimming and lounging - check out our pool and our floating breakfast - or - the beaches are not far away. Feel for entertainment....you can book our preferred entertainer! ....SAXOPHONIST....RICARDO SEALES!!!!!!

4.79 out of 5 average rating, 14 reviews

Apartment in Tobago

Gleneagles Nest 2

Cozy, nest-styled, self-contained apartment located in Mt. Irvine, Tobago. Our accommodation is conveniently just a 5 minute walk from the popular Mt. Irvine beach and Backbay Salt Pools/Beach. very spacious (450 square foot) and all self- contained. Each apartment consists of 2 open concept bedrooms, a bathroom, living space and kitchen. The entire apartment sleeps 4 persons comfortably (2 persons per bed). Accommodations for more guests can be arranged upon request.

A multi-level building is nestled among lush greenery, positioned on a hillside overlooking tranquil waters. The structure features wooden elements and spacious balconies that provide views of the surrounding landscape. Sunlight filters through the trees, creating a serene atmosphere.

5 out of 5 average rating, 11 reviews

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!

4.85 out of 5 average rating, 73 reviews

A cozy sleeping area features a spacious bed covered with a coral quilt. Natural light enters through green-shuttered windows, illuminating the polished concrete floor. A simple wooden bedside table and a chair are visible, framed by the entrance marked with lush greenery.

Apartment in Mt Irvine

Immersive, natural studio in enchanting garden

A fully appointed studio apartment located in a lush tropical garden resplendent with fruit trees, flowers, and herbs. The architectural design is natural Caribbean modern with local cedar cabinets and Samaan countertops overlayed on a polished concrete floor. Large sliding doors open the entire apartment up to the outdoors. A carpet of grass to sun bathe on or watch the stars. Al fresco dining area to enjoy the cool Caribbean nights.

4.8 out of 5 average rating, 10 reviews

A sunny exterior view of a Caribbean-style villa is presented, showcasing a yellow facade and a landscaped front yard. Lush palm trees and neatly trimmed hedges frame the entrance, with a clear path leading to the door, set against a backdrop of blue skies.

Home in Lowlands

Easy As Villa

Situated in the 20 acre gated Tobago Plantations Estate, this fully furnished Colonial/Caribbean style villa sits on the edge of a well - manicured 18 -hole golf course and opposite to two and a half miles of beach. The Villa is among a select handful of premiere Tobago luxury rentals and is located in the Tobago Plantations Estate, one of the most exclusive communities on this enchanting island in the South Caribbean Sea.

4.8 out of 5 average rating, 10 reviews

A refreshing swimming pool sits next to the covered veranda, offering views of the shimmering lake and surrounding trees. The clear blue sky with scattered clouds enhances the serene outdoor setting, providing a peaceful atmosphere for relaxation.

Villa in Canaan

The Lake House - Samaan Grove

This charming and elegant villa is in a prime location overlooking one of the Samaan Grove lakes. The single story villa is spacious and relaxing and has a covered veranda over looking the lake and an open terrace by the private swimming pool. Each bedroom is a/c and has a bathroom ensuite. The villa comfortably sleeps 8 people. Off road parking for 2 cars.

4.9 out of 5 average rating, 229 reviews

Two small yellow birds are perched among vibrant green leaves, with sunlight filtering through the foliage. The surrounding palm fronds create a tropical backdrop, enhancing the natural beauty of the scene.

Loft in Crown Point

Caribbean Loft close by the sea

The sun-flooded loft is as pretty and comfortable on the inside as on the outside, sporting stylish and comfy furniture and a nice terrace with a hammock. In the very close vicinity you find the island's prettiest beaches as well as abundant faciliti

A serene veranda is featured, with a light blue table set for dining. Tall palm trees surround the area, providing a tropical ambiance. A view of the distant sea can be seen in the background, adding to the relaxed atmosphere of the space.

Apartment in Black Rock

4.73 out of 5 average rating, 115 reviews

Grafton Heights

This is an unique apartment with an intriguing interior. It is very airy surrounded by colorful gardens. Grafton Beach is only a short walk away. The sunsets over the Caribbean Sea are legendary. You will be welcomed and made most comfortable.

The exterior view of Leapfrog shows a rustic-style apartment beneath a larger villa. Lush greenery surrounds the building, with tropical plants and trees enhancing the natural setting. Steps lead up to the entrance, and the balcony features wooden accents and decorative railing.

4.74 out of 5 average rating, 27 reviews

Leapfrog, Castara, Tobago

Leapfrog is a self-contained apartment located in the idyllic village of Castara on the north (Caribbean) coast of the island of Tobago. It is a 5 minute stroll from two beautiful beaches and the village centre.

Popular amenities for Scarborough Smoke-Friendly Accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Smoking-friendly apartment rentals

The exterior of a multi-level building is showcased, surrounded by lush greenery and colorful flowering plants. A pathway leads through a well-maintained lawn, while a covered balcony with white railings offers shaded outdoor space. The building features a green metal roof and a well-manicured landscape.

Apartment in Scarborough

4 out of 5 average rating, 8 reviews

Crown apartment

A functional kitchen is presented with wooden cabinetry and tiled flooring. Essential appliances are included, such as a refrigerator, oven, and microwave. Natural light fills the space through window treatments featuring checkered patterns, adding a warm touch to the cooking area.

Apartment in Bon Accord

4.8 out of 5 average rating, 5 reviews

Claudia's comfortable Studio Apartment

4.9 out of 5 average rating, 68 reviews

A two-story yellow house is set on a lush landscape, featuring palm trees and vibrant flora. A curved driveway leads to the entrance, framed by a decorative gate. Balconies are visible on the upper level, surrounded by greenery.

Apartment in Black Rock

2 BR steps to the beach, & pool.

4.83 out of 5 average rating, 41 reviews

Porridges Place

Two champagne flutes are positioned on a balcony railing, capturing the moment as sparkling wine is poured. The background features a vibrant sunset over the beach, surrounded by palm trees, creating a serene atmosphere.

Apartment in TT

Beachfront Bliss

A deck area features a table with two chairs, offering a serene view of the water and greenery. The surrounding bamboo fencing provides privacy, while lush trees enhance the natural setting, creating a peaceful retreat.

5 out of 5 average rating, 3 reviews

The Peach Room

4.9 out of 5 average rating, 89 reviews

A clear blue pool is surrounded by a terracotta patio, with comfortable lounge chairs arranged nearby. Lush greenery is visible in the background, alongside a view of the ocean under a clear sky. The area offers a spacious and relaxing environment.

Apartment in Plymouth

Cabanas 3 with Private Gazebo; Walk to Beach

A small rectangular hot tub is visible, featuring clear water illuminated by soft blue lighting. The tub is surrounded by a smooth white surface, with a contrasting dark wooden deck nearby.

Apartment in Scarborough

4.67 out of 5 average rating, 3 reviews

Breeze Manor apartment 2

Smoke-Friendly Holiday Houses

This spacious villa features a red-tiled roof and an expansive terrace overlooking a large swimming pool. Lush gardens surround the property, with various palm trees and colorful landscaping visible in the background. The peaceful hillside adds a natural backdrop to this serene setting.

Home in Western Tobago

4.71 out of 5 average rating, 14 reviews

The Brash Villa of Tobago/Reef View

The modern condo exterior is highlighted by soft purple and white lighting, showcasing a sleek stone facade. Each unit features a balcony and individual entrances, with lampposts illuminating the pathway. A spacious parking area is visible in the foreground.

Home in Tobago

Deja Blue Villa Tobago

A spacious poolside area is depicted with two comfortable chairs and a wooden table on a covered patio. Decorative string lights are draped overhead, casting a soft glow. The pool features a floating lounge and is surrounded by lush greenery.

Home in Black Rock

4.83 out of 5 average rating, 29 reviews

Miles Away - for lovers of sunsets & sea views

A clear blue infinity pool is presented, reflecting the sky. Palm trees frame the view, and lounge chairs are positioned nearby, inviting relaxation. The backdrop features lush greenery and distant ocean views, creating a tranquil outdoor setting.

Home in Parlatuvier

4.84 out of 5 average rating, 32 reviews

Rainbow Loving Caribbean Lifestyle

4.85 out of 5 average rating, 53 reviews

The two-bedroom guesthouse features a welcoming living area with soft seating and large windows, allowing natural light to fill the space. A dining area with a table and chairs is adjacent to the kitchen, which showcases modern appliances and ample countertop space.

Home in Scarborough

Palm Haven - Home away from home

Home in Plymouth

New place to stay

Casa de Morrison - 3 bedroom House

A clear swimming pool is seen in the foreground, surrounded by a tiled deck. Shaded lounging areas and white lounge chairs are positioned nearby. The two-story villa is visible in the background, featuring a red-tiled roof and multiple balconies, set against a lush green landscape.

Home in Scarborough

4.75 out of 5 average rating, 4 reviews

Casa Clara - a bright & spacious holiday retreat

4.95 out of 5 average rating, 22 reviews

A modern single-story house is set against a bright blue sky. The entrance is approached via a short pathway, flanked by green grass. Two parked cars are visible in the driveway, with neighboring structures partially seen in the background.

Home in Signal Hill

Winston’s Court (Single Room)

Other smoking-friendly holiday rentals

A spacious bed is dressed in a bright green cover, complemented by decorative cushions featuring stripes and polka dots. Light-colored walls and tiled flooring create a fresh and airy feel, while bedside sconces provide soft lighting.

Private room in Tobago

4.89 out of 5 average rating, 9 reviews

Eve’s Retreat

Private room in Crown Point

A room features a comfortable queen bed with a suspended net, complemented by bedside tables. A small dining area is visible in the corner. The space is well-lit, showcasing a light-coloured wall and tiled flooring, creating a relaxing atmosphere.

4.8 out of 5 average rating, 117 reviews

APT 4 -Studio, Carolina Point, Near Pigeon Point

A light and inviting room is furnished with two beds, one with a decorative towel arrangement. The kitchenette features wooden cabinetry and essential appliances, including a refrigerator and microwave. Natural light filters through the window, adorned with striped curtains, enhancing the warm color palette of the space.

Private room in Castara

4.67 out of 5 average rating, 30 reviews

Community vibes alive

Private room in Crown Point

4.63 out of 5 average rating, 8 reviews

Candles in the wind. Private room

Private room in Parlatuvier

A private pool reflects the clear blue sky, surrounded by lush greenery and palm trees. The pool area is framed by a stone edge, offering views of the water and distant mountains. Multiple lounge chairs are present nearby, inviting relaxation.

4.96 out of 5 average rating, 46 reviews

Beach Side Apartments (Apartment 2)

4.85 out of 5 average rating, 67 reviews

A two-story building is framed by well-tended floral gardens, with pots of colorful plants positioned along the path. A balcony adorned with decorative railings extends from the upper level, while a bright blue sky casts a cheerful light on the property.

Private room in Canaan

Serenity Apartments

Private room in Scarborough

5 out of 5 average rating, 5 reviews

Cozy Room @ Hope Cottage Guest House