Holiday rentals with a pool in Port of Spain

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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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Superhost
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
4.92 out of 5 average rating, 122 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 favourite
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.
Apartment in Port of Spain
5 out of 5 average rating, 124 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 .

Guest favourite
A private backyard pool is showcased, illuminated in calming blue tones under the night sky. Surrounding the pool, there is a stone wall and soft lighting that creates a serene ambiance. An outdoor seating area is visible nearby, enhancing the outdoor space.
Home in Chaguanas Borough Corporation
4.92 out of 5 average rating, 102 reviews

Cheerful 2-bedroom home with a private pool.

This exclusive location is conveniently situated near all amenities, simplifying your trip planning. Situated in a secure gated community in Chaguanas, Trinidad, it features a private backyard pool. Just a one-minute drive from the highway and a mere two-minute drive from the primary shopping districts of Heartland Plaza and Price Plaza and downtown Chaguanas. Moreover, it is just a 30-minute drive from the capital, Port of Spain, and only 20 minutes from the Piarco International Airport.

Top guest favourite
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.
Apartment in Port of Spain
5 out of 5 average rating, 40 reviews

*Luxurious Condo in One Woodbrook!* PoS

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!!!

Guest favourite
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.
Flat 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.

Guest favourite
A tranquil pool area is surrounded by a spacious deck, featuring comfortable lounge chairs and a shaded dining space. Potted plants add greenery to the setting, while string lights subtly enhance the ambiance above the pool.
Flat in Port of Spain
4.92 out of 5 average rating, 26 reviews

Prime location - River Sand Apt

You can't beat this location! If you love food, this apartment has over 30 food places within its vicinity. If you like to walk, then take a 20 mins stroll to the Savannah. If not a 7 min drive will do the trick. You can relax on our spacious pool deck or go for a swim! The Sands of Time compound is absolutely stunning. The building has charm with its steps and layered levels. Plus it is unique as it was designed by an Interior Designer who has done projects across the Caribbean.

Top guest favourite
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.
Apartment in Piarco
4.95 out of 5 average rating, 161 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.

Guest favourite
A modern cottage with a distinctive architectural design features a sloped roof and a mix of soft colors on its façade. Natural stone accents are visible in the landscaping, complemented by a well-kept lawn and outdoor seating areas, creating a relaxing exterior.
Guest house 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.

Superhost
A modern kitchen features sleek white cabinetry and a minimalist design. Counter space is utilized for food preparation, complemented by gray patterned backsplash tiles. Two place settings are arranged, with matching plates and mugs. Stainless steel appliances, including a microwave and refrigerator, are also visible.
Guest suite in San Juan
4.9 out of 5 average rating, 136 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

Guest favourite
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, 71 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.

Guest favourite
The sleeping area is defined by a green accent wall, featuring a spacious bed dressed with white linens and a decorative pillow. A stack of neatly rolled towels is placed on a corner of the bed. A brown bench sits at the foot of the bed, adding functional style.
Flat in Belmont
5 out of 5 average rating, 20 reviews

Stacys Place #4: Studio Apartment

This studio apartment is ideal for any single traveler or couple seeking convenience of location. Surprisingly spacious with multiple living spaces and optimal functionality. Guests most certainly are delightfully surprised that this space lacks nothing. It is private and checks all the boxes of a home. A hotel room allure with an at home vibe. Perfect for work from home or traveling for business.

Top guest favourite
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
4.91 out of 5 average rating, 127 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.

Popular amenities for Port of Spain rentals with a pool

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

  • Total rentals

    180 properties

  • Nightly prices starting at

    £30 before taxes and fees

  • Total number of reviews

    3.5K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    180 properties include access to wifi