Holiday rentals with a pool in Port of Spain

Find and book unique homes with a pool on Airbnb

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

  • Total holiday rentals

    Explore 210 holiday rentals in Port of Spain

  • Nightly prices starting at

    Port of Spain holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,590 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    200 of Port of Spain holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Port of Spain rentals

  • 4.8 Average rating

    Port of Spain stays are highly rated by guests – averaging 4.8 out of 5!

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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Top guest favourite
Home in Goodwood Park Extension
4.91 out of 5 average rating, 22 reviews

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.

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Top guest favourite
Apartment in Piarco
4.98 out of 5 average rating, 41 reviews

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.

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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
4.98 out of 5 average rating, 139 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 .

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Guest favourite
The cabin is framed by a lush garden featuring vibrant yellow flowers carpeting the ground. An inviting wooden exterior, complemented by large windows, allows natural light to fill the space. Surrounding trees add to the tranquility of this serene hillside setting.
Holiday home in Port of Spain
4.97 out of 5 average rating, 66 reviews

Le Chalet

Located 25 minutes from the airport and nestled in the hills of Maracas valley, this cabin is just a 7 minute drive from the trail head of the highest waterfall in Trinidad at 300 feet and 3 minute drive from the hummingbird sanctuary. Also located nearby is the Ortinola estate where you can make your own chocolate. Please feel free to ask about airport transfers and additional tours of the island that we offer. Our home is very family oriented, we do not allow events or large gatherings.

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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
4.94 out of 5 average rating, 126 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.

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Superhost
Apartment in Port of Spain
4.85 out of 5 average rating, 66 reviews

Deluxe 2BR Condo • Elegant • Homey • Amazing Views

✨ About This Space ✨ Recharge, reflect, and stay productive in this classic executive 2-bedroom, 2- bath condo located in POS at One Woodbrook Place. Perfectly suited for business travelers, executives, consultants, couples, friends and family. This well-appointed space offers the ideal balance of privacy, luxury, convenience and location. Just steps away from top restaurants, entertainment and key business hubs, this home away from home is your space for productivity and relaxation.

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Guest favourite
The condominium towers rise against a clear blue sky, featuring balconies and large windows. Lush palm trees line the base, complementing the modern architectural design with warm tones and varying heights, creating a distinct city skyline.
Flat in Port of Spain Corporation
4.91 out of 5 average rating, 54 reviews

One Great Place to Stay

Ideal location for short and long stay. Conveniently located in centric Woodbrook. This luxurious condo with all inclusive facilities works both as a getaway site as well as a starting point with access to it all. Saint James’ western Main road is known as the street that never sleeps, The Savanah, Imax and Cinema One, Pharmacies, Banks, Shopping malls, Carnival prime location, Car rentals, Ariapita Avenue (The Avenue) Restaurants all within walking distance of this great place to stay.

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Guest favourite
A private pool is framed by a wooden deck and lush greenery, creating a calm outdoor space. The surrounding building features large windows that allow light to filter in, with carefully arranged plants adding a touch of color to the environment.
Flat in Port of Spain
4.94 out of 5 average rating, 105 reviews

Carnival safe 1BR, pool, kitchen, in St. Anns

Located in an attractive and safe neighborhood our 1 bed self contained apartment features 1 queen bed, ample closet space along with a spacious living, dining and kitchen area for your comfort. Fast wifi, SmarTV with Netflix signed in, BBC, YouTube apps. The kitchen is fully equipped with utensils, small appliances, washer & dryer so everything you need is in one place. Outdoor garden and pool area to enjoy. Easy access to Port Of Spain, the Savannah, restaurants, grocery and shops.

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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, 202 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.

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Superhost
Guest suite in San Juan
4.89 out of 5 average rating, 149 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 - the call and response of at least 10 species of birds, shady fruit trees, as well as the comforts of modern day life. Only 30 minutes drive from the beautiful Maracas Beach, this modern property is also in walking distance of supermarkets, pharmacies and local food joints. It's a mere 20 minutes from the Queen's Park Savannah.

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Guest favourite
Flat in Port of Spain
5 out of 5 average rating, 8 reviews

Upscale 2-beds, 2 baths oasis

Escape to our stunning 2-bedroom, 2-bathroom condo for a relaxing getaway. This beautifully appointed unit features: - A modern kitchen equipped with appliances - A spacious living area - Two bedrooms, each with en-suite bathrooms - A private balcony offering ocean and city views - A dedicated workspace Amenities: - 24-hour security - Swimming pool - Gym - Parking - In-house laundry facilities This stylish accommodation is perfect for a group trip!

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Top guest favourite
A bright living area features a green sofa and a dark leather couch, complemented by a glass coffee table. Large sliding doors open to a balcony with outdoor seating, offering views of the mountains. Artistic decor adorns the walls, enhancing the space.
Flat in Port of Spain
5 out of 5 average rating, 38 reviews

Beautiful and Spacious One Woodbrook Place Apt

Beautiful and spacious apartment in One Woodbrook Place, the best located upscale residence in Trinidad & Tobago. Quiet and secure, yet steps away from restaurants, bars, clubs and main entertainment areas, some within the complex. A short walk to the Queen’s Park Savannah, the heartbeat of Port of Spain, as well as offices of multinational companies, embassies and private medical facilities.

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Popular amenities for Port of Spain rentals with a pool

When is the best time to visit Port of Spain?

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