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Vacation rentals with a pool in Port of Spain

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Port of Spain

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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A serene balcony features a hammock and a small dining set with two chairs, all placed on lush green turf. A telescope is positioned for panoramic views of the ocean and surrounding landscape, complemented by bright sunlight streaming in.

Place to stay in Port of Spain

4.91 out of 5 average rating, 117 reviews

Enchanted Forest:Projector/Pool/Jacuzzi/King Bed

Step into the enchanting embrace of our forest-themed villa nestled in the heart of Port of Spain. Elegance meets adventure in this central haven, where captivating ocean views and stunning sunsets, with boats dotting the horizon, await your arrival. This space promises an experience beyond the ordinary. With proximity to shopping malls, restaurants, nightlife and more. Our villa is the perfect blend of convenience and serenity, making it an ideal retreat for travelers seeking the extraordinary.

Top guest favorite

An inviting living area features two sofas, an armchair, and a coffee table. A dining table for eight is positioned under a ceiling light. Large windows offer views of the surrounding hills, complemented by warm-toned walls and decorative accents.

Condo in Woodbrook

4.98 out of 5 average rating, 59 reviews

Island Charm. Chic Escape. Adventure Await

🛏️ 3 bedrooms w/1 king & 2 queen. Lots artwork and 2 1/2 baths 🍽️ Full kitchen, 8-seater dining, 3 TVs, 1 of 75" 🌇 Balcony w/ skyline, hills, parks & some sunset views 🏊 Private pool, secure underground parking 📍 Walk to Queen’s Pk. Savannah, Botanic Gardens, restaurants, movies & more 🥁 Steps to steel pan yards, theatres, culture 🌿 30 mins drive to north coast: Maracas Bay, Paramin, rainforest, etc 🏙️ Shops, banks, gyms, close by ✨ Perfect for couples, families or business

Top guest favorite

An open-concept living area is highlighted by modern furnishings, featuring a large sectional sofa and a sleek entertainment unit. The adjoining kitchen boasts contemporary appliances and an island, with warm wooden flooring enhancing the spacious feel. Soft, natural light fills the space through recessed lighting.

Condo in Port of Spain

5 out of 5 average rating, 122 reviews

Contemporary Port of Spain Condo

Enjoy a stylish experience at this centrally located place. The unit it located steps away from any amenity you can think of. The best restaurants the island has to offer, banking, supermarkets, pharmacy, recreation, hospitals and much more. You can’t ask for a better or safer location. Perfect for your visit to Trinidad or for a luxury staycation. This unit aims to cater to your every need so your vacation or business trip is an enjoyable one. You will feel totally relaxed at this unit .

A large outdoor pool is surrounded by a tiled patio, offering expansive views of the nearby hills and sky. Sunlight reflects off the water's surface, while lush greenery and palm leaves frame the scene, highlighting the serene atmosphere of the complex.

Condo in Port of Spain

5 out of 5 average rating, 37 reviews

*Carnival ‘26 open!* Luxurious Condo in Woodbrook!

You’ll enjoy easy access to everything from this centrally located place, located in the most exclusive building in Port of Spain, Trinidad. -Secure & gated entrance -Parking included -5 minute drive to Ariapita avenue (“The Ave”) Our LUXURIOUS condo at 1 Woodbrook Place will make you feel at home while being the perfect getaway. Gym, Pool, Restaurants, Bars, IMAX Theater, Shopping, & NightClub are all conveniently located in the complex. Enjoy Amazing views of the city & the hills!!!

The living area is comprised of stylish seating, including two armchairs with yellow and white stripes and plush cushions, alongside a comfortable grey sofa. A wall-mounted TV is positioned above a decorative table. Framed artwork enhances the modern aesthetic of the space.

Apartment in Woodbrook

4.89 out of 5 average rating, 66 reviews

Exquisite 1BR • Modern • Vibrant • City View

✨ About This Space✨ Welcome to your private escape at One Woodbrook Place — a sleek, 1 bedroom, 1 bath apartment crafted for travelers who appreciate refined comfort, modern amenities and convenience. Step into a bright, thoughtfully designed space featuring an open-concept layout and amazing city views by day and dazzling lights by night. Whether you're a business traveler, consultant, digital nomad, or simply escaping for a relaxing getaway, this apartment is exactly what you need.

Top guest favorite

An outdoor area features an infinity pool complemented by a jacuzzi, surrounded by well-maintained gardens. Lush green hills provide a scenic backdrop, and various tropical plants line the edges of the patio, creating a tranquil setting.

Apartment in Port of Spain

4.98 out of 5 average rating, 52 reviews

Cascade Mountain View Oasis

Situated 10 minutes from Port of Spain and nestled in Cascade in the Northern Mountain Range, lies the beautiful Cascade Mountain View Oasis. Experience a safe, peaceful haven for the ideal getaway. Equipped with an infinity pool and jacuzzi that overlooks the view of the mountains. 7 minutes from the historic Queens Park Savannah, home of our iconic carnival celebrations, 12 minutes’ drive from the popular Ariapita Avenue with its diverse array of restaurants, bars and night life.

Top guest favorite

A modern living area features a plush sectional sofa with decorative pillows, oriented towards a sleek glass coffee table. A large flat-screen TV is mounted on a stylish accent wall, with calming blue lighting enhancing the contemporary design. An open layout is visible, leading to a well-appointed kitchen.

Condo in Piarco

4.95 out of 5 average rating, 157 reviews

The Pad Luxury, Piarco Trinidad (With Pool)

The Pad: Modern Condo Near Piarco International Airport Dive into a realm of elegance and ease at "The Pad at Piarco" – our contemporary 2-bedroom condo nestled within a secure gated community. Situated just a stone's throw away from Piarco International Airport. This refined haven is crafted for those with an eye for luxury. Cool off at the swimming pool or relax in the plush interiors. The Pad at Piarco is in close proximity to 24hr gas stations, groceries, and vibrant malls.

A saltwater pool is surrounded by tropical plants and flowering shrubs. The pool deck features beige stone tiles, and a jacuzzi is located nearby. A modern cottage structure with large windows and a staircase can be seen in the background.

Guesthouse in Saint Joseph

4.84 out of 5 average rating, 103 reviews

Vista Stays ... The Cottage

Looking for a quiet and peaceful setting away from the hustle and bustle of everyday living, look no further. Our modern cottage is set in a rainforest environment with mountain views and tropical garden for relaxation. Rejuvenate in the refreshing salt water pool and jacuzzi. Leave the cooking to our Chef, as we serve up breakfast, lunch and fine dining dinner experiences. It gets even better as our massage therapist pamper you with massage and spa treatments tailored for you.

A serene swimming pool features a clear blue surface, surrounded by a tiled deck. Lush greenery, including potted plants, enhances the inviting ambiance. The property’s entrance includes large French doors, allowing natural light to flow into the space.

Guest suite in San Juan

4.9 out of 5 average rating, 135 reviews

Oasis, Your home away from home.

Nestled at the foothills of the Northern Range in the lush, peaceful valley of Santa Cruz, this property offers the beauty of nature - birds chirping in the morning, fruit trees. as well as the comforts of modern day life. Only 30 minutes drive from the beautiful beaches of the north coast in general and Maracas Beach in particular, this modern property is also in walking distance of supermarkets, pharmacies and local food joints. It's a mere 20 from the Queen's Park Savannah

A private pool area is highlighted, featuring two connected pools with a tile border. A gazebo is situated nearby, surrounded by lush greenery. Decorative lamps line the pool's perimeter, casting soft light in the open space.

Home in Las Lomas #2

4.87 out of 5 average rating, 195 reviews

Nature Getaway Resort with private pool

Lovely 2 bedroom home plus loft with resort type amenities tucked away in the woods but just a 10 min drive from the airport. The house comes equipped with a full kitchen which includes - Gas burner stove/oven, double door refrigerator, dish washer, microwave and toaster oven. All utensils and cookware is included. There is a private pool (heated if required) with gazebo. There are four (4) hammocks for relaxing, kids play park with two slides and swings.

A shimmering swimming pool is framed by elegant columns and lounge chairs, inviting relaxation. The surrounding area features well-maintained gardens and stylish architecture, with a backdrop of bright blue skies.

Villa in Port of Spain

4.85 out of 5 average rating, 67 reviews

Luxury 3BR | Maraval | Pool | Gated With Security

Experience luxury and comfort in this stunning 3-bedroom, 3.5-bathroom villa in Maraval, Trinidad. Fully equipped with modern amenities, this serene retreat is perfect for a relaxing getaway. Conveniently located just minutes from restaurants, pharmacies, grocery stores, and shopping plazas, everything you need is within easy reach. Nestled in a gated community with 24-hour security, this home ensures a safe and peaceful stay for all guests.

Top guest favorite

A spacious pool area is surrounded by lush tropical plants and palm trees. The inviting pool features a hot tub nearby. Natural stone borders the pool, while a smooth patio provides a serene outdoor environment, enhancing the feeling of relaxation amidst the verdant garden.

Guest suite in Port of Spain

4.9 out of 5 average rating, 126 reviews

Tropical Haven - 2 bedroom apartment in Maraval

This spacious and tropical apartment has two bedrooms and two bathrooms, as well as a large open-plan kitchen and living room. There is also a luxurious pool in the lush garden. It is located in a quiet neighbourhood on the St. Andrews Golf Course in Moka and is only 20 minutes away from Maracas Beach or Port of Spain.

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Popular amenities for Port of Spain rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A two-story guest house features arched windows and a balcony on the upper level. In the foreground, a decorative fountain is surrounded by a tiled area and a shimmering pool, with various outdoor seating options visible under the covered patio.

Home in Chaguanas Borough Corporation

4.92 out of 5 average rating, 12 reviews

Point Manor

A comfortable living area features a combination of brown and grey seating, complemented by colorful throw pillows. Natural light filters through sheer curtains, enhancing the space. A round glass table sits on a patterned rug, while two area mats define the seating arrangement.

4.83 out of 5 average rating, 46 reviews

The Relaxant

A private pool is framed by decorative white lattice fencing. The crystal-clear water of the pool reflects the greenery surrounding the area, creating a tranquil outdoor space. Lush trees provide shade and enhance the serene atmosphere of the backyard.

Home in Port of Spain

4.7 out of 5 average rating, 33 reviews

Four bedroom oasis in town with private pool

A tranquil pool area is surrounded by lush greenery, featuring tall tropical plants and a stone patio. The pool's clear water reflects the sky above, creating a serene retreat in the outdoor space.

Home in Port of Spain

4.86 out of 5 average rating, 7 reviews

Ankara Hill

A spacious bedroom is presented, featuring a large bed with a patterned blanket. A mounted television is visible on the wall opposite a set of built-in cabinets, while natural light enters through the window adorned with blinds.

Home in Tacarigua

4.9 out of 5 average rating, 51 reviews

The Prestige

A two-story rental house is shown from a lower angle, highlighting its modern architecture. The exterior features large windows and a balcony. The clear blue sky creates a bright backdrop, while lush greenery is visible in the foreground.

Home in Maraval

Maraval Hilltop Views

Top guest favorite

A bright outdoor space features a stunning pool complemented by a stone patio. Lounge chairs are positioned near the water, while a stylish seating area with a canopy sits to one side. Lush greenery surrounds the area, enhancing a serene atmosphere.

Home in Saint Clair

5 out of 5 average rating, 9 reviews

Pandora's Zen

An inviting pool area showcases a uniquely shaped swimming pool with clear blue water. Two charming dolphin sculptures, each with water flowing from their mouths, are positioned beside lush green plants and a decorative stone fountain, creating a relaxing atmosphere.

Home in Tunapuna/Piarco Regional Corporation

5 out of 5 average rating, 8 reviews

Esther’s Retreat:

Condo rentals with a pool

A large swimming pool is surrounded by a spacious patio area, featuring a shaded gazebo to the side. Lush greenery frames the scene, while a light fixture stands beside the pool. A sign nearby provides pool rules for guests.

Condo in Petit Valley

4.92 out of 5 average rating, 13 reviews

Diamond H Apartments

A comfortable living area features a gray sectional sofa adorned with colorful pillows. A glass coffee table rests on a vibrant area rug, while a wall-mounted television is positioned opposite the seating. Natural light enters through two large windows framed by shades.

Condo in Saint Augustine

4.9 out of 5 average rating, 82 reviews

What a feeling!!!

Condo in Petit Valley

4.86 out of 5 average rating, 21 reviews

2nights-$299*Spec VClose to POS:Peaceful 2BR Apt

Condo in D'Abadie

4.83 out of 5 average rating, 71 reviews

Executive 3 Bedroom Condo With King Bed & Pool

A contemporary living area features a light-colored sectional sofa accompanied by a black throw blanket. A patterned area rug lies beneath, while a modern chandelier hangs from the ceiling. A large television is positioned on a black console, complemented by framed artwork on the walls.

Condo in Woodbrook

4.77 out of 5 average rating, 53 reviews

Cozy 2BR condo in Woodbrook, Port-of-Spain

A serene outdoor area is depicted, featuring a lush green lawn and a tranquil pool surrounded by palm trees. Gazebo structures with red roofs provide shaded seating, with the calm coastal waters visible in the background.

Condo in Port of Spain

4.86 out of 5 average rating, 72 reviews

Luxury Condo with Amenities on the Sea

A grey sectional sofa is featured, accompanied by two decorative pillows. A textured blue throw is draped over the arm, adding a layer of comfort. Natural light filters through sheer curtains, while a landscape painting adorns the wall, creating a relaxed living area.

Condo in D'Abadie

5 out of 5 average rating, 15 reviews

Luxurious 3BR/2BA condo with Pool

A spacious living area features a comfortable sofa against a neutral wall. A flat-screen television is mounted on the wall, accompanied by a sleek white media console. Natural light floods the space through sliding glass doors with vertical blinds, enhancing the modern design.

Condo in Piarco

4.87 out of 5 average rating, 30 reviews

Lux Casa TT- Stylish 2 bedroom condo with pool

Other vacation rentals with a pool

A modern living area features a light-colored sofa adorned with floral-patterned cushions, positioned across from a round wooden coffee table. A mirror adds dimension to the wall, while a dining space with sleek chairs is visible in the background, complemented by contemporary artwork.

Apartment in Saint Joseph

4.74 out of 5 average rating, 92 reviews

The Aqua Terra

A living area is presented with a glass coffee table in the foreground, complemented by a modern sofa. A shelving unit holds framed artwork and a television. Natural light filters through sheer curtains, creating a bright atmosphere. A large leafy plant adds a touch of greenery.

Apartment in Woodbrook

5 out of 5 average rating, 4 reviews

Luxury 1-Bd Apt Woodbrook

Villa in Tunapuna/Piarco Regional Corporation

5 out of 5 average rating, 13 reviews

Luxury Vacation Villa in Valsayn

A modern kitchen area features sleek cabinets and stainless steel appliances, including a refrigerator and microwave. A white marble countertop with three black bar stools creates a dining space. The living area is visible, showcasing a flat-screen TV mounted on the wall and a dark sofa.

Apartment in Maraval

4.74 out of 5 average rating, 34 reviews

2-bedroom Tranquil Maraval Retreat

Top guest favorite

A swimming pool is depicted with clear blue water and a small waterfall feature. Colorful beach balls float on the surface. Lush greenery surrounds the area, providing a refreshing contrast. A fence outlines the pool, ensuring safety and privacy.

Apartment in Belmont

5 out of 5 average rating, 8 reviews

Tranquil Oasis in Port of Spain

A private pool area features a sparkling swimming pool surrounded by green artificial grass. The wall behind is adorned with a striking abstract mural, while a flat-screen television is mounted nearby. Comfortable seating options can be seen, making it suitable for relaxation and entertainment.

Apartment in Port of Spain

5 out of 5 average rating, 5 reviews

Lavish Livin’

A modern living area features a sleek white entertainment unit positioned under a large, wall-mounted television. The unit is complemented by a textured wall in soft tones, and a decorative mirror is visible to the left, while a green plant adds a touch of nature.

Condo in Piarco

4.86 out of 5 average rating, 14 reviews

2 BR Modern Condo Piarco | Pool & Gym

A modern apartment complex is observed against a bright blue sky, surrounded by lush palm trees. The buildings feature multiple stories with balconies, and a well-maintained pathway leads to a serene water feature situated among garden landscaping.

Apartment in Woodbrook

4.76 out of 5 average rating, 21 reviews

Apartment in One Woodbrook Place

Quick stats about vacation rentals with a pool in Port of Spain

Total rentals
180 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
100 properties are a good fit for families
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wifi availability
170 properties include access to wifi

Destinations to explore