Holiday 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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Superhost
A modern kitchen with sleek black appliances is featured, complemented by a center island with bar seating. Lush greenery is present throughout the space, including potted plants. Decorative baskets and artistic sculptures enhance the visual interest of the room, while large windows allow natural light to illuminate the area.
Holiday home in Port of Spain
4.85 out of 5 average rating, 152 reviews

Jungle Oasis: Sea&City Views with Ruby Sunsets

Experience the ultimate escape at our luxurious villa. With breathtaking views of the Caribbean Sea, a serene environment, and fully-equipped amenities, this is the perfect getaway for couples, families, and business professionals. Let the cool windward breezes rejuvenate your soul while gazing upon the majestic boats sailing towards the horizon, painting the sky with a stunning array of ruby hues during the unforgettable sunsets. Book now and indulge in the tranquility of this tropical paradise

Guest favourite
Villa in Diego Martin
4.93 out of 5 average rating, 100 reviews

Garden Oasis 2: Villa with Private Pool

A stylish and spacious two-bedroom with a media lounge room located in one of the most desirable neighbourhoods in Trinidad. This duplex villa is fully serviced, and designed to define opulence. It awaits guests in a completely private and serene setting, where the only desire is to never leave. This property is located close to shopping, attractions, and an array of dining options. It is outfitted with five star furnishings, has a private pool, and BBQ grill to enhance the overall experience

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, 129 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
4.93 out of 5 average rating, 107 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.

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.

Superhost
A modern kitchen is displayed, featuring white cabinetry and a stainless steel refrigerator. Natural light enters through a window with sheer curtains. An open layout includes a smooth countertop that separates the kitchen from an adjoining space, equipped with small appliances and a microwave.
Flat in Port of Spain
4.83 out of 5 average rating, 12 reviews

Modern safe 1BED - gated,pool,kitchen,WiFi,Netflix

Located in an attractive and safe neighborhood our modern 1 bed self contained apartment has a queen bed, ample closet space with a spacious living, dining and kitchen area for your comfort. SmarTV with Netflix signed in & BBC, YouTube & fast WIFI. The kitchen is fully equipped with utensils, all 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.

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, 170 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
4.91 out of 5 average rating, 138 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

Superhost
A stylish living room features a beige sofa and a polished wooden coffee table, topped with a decorative bowl. Floor-to-ceiling curtains frame a sliding glass door that opens to a private balcony with two outdoor chairs, allowing natural light to brighten the space.
Flat in Woodbrook
4.75 out of 5 average rating, 59 reviews

Graceful 1BR Suite • Balcony Views • Cozy • Secure

✨ About This Space✨ Step into your private city-view retreat at One Woodbrook Place — In the heart of Port of Spain. Perfect for business travelers, executives, consultants, couples, or long-stay explorers. This 1 bedroom, 1 bath condo combines luxury, security, and unbeatable location. Enjoy stunning relaxing views, Wi-Fi, modern amenities, and 24/7 secure parking — all steps away from dining, nightlife, and cultural events.

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

Luxurious 1-Bedroom Condo (With Pool)

Take it easy at this unique and tranquil getaway. This gated compound is located in early Maraval, and is only 5 minutes away from the supermarket, food hubs and 2 of the largest pharmacies in Trinidad (Starlite and Superpharm). Perfect for travelers or business professionals. It is also 25 minutes away from the beautiful Maracas Bay, 20 minutes from Port of Spain and 15 minutes from Ariapita Avenue!

Superhost
Flat in Port of Spain
4.95 out of 5 average rating, 21 reviews

Prime Location 1BD | Pool | Gated

Experience the perfect home away from home in Maraval, Trinidad! Nestled on Valleton Avenue, this charming1-bedroom, 1.5 bathroom, fully equipped apartment offers a serene retreat with modern amenities and convenient proximity to nearby attractions. It is located within a minutes walk or drive away from restaurants, pharmacies, grocery stores, and shopping plazas and the Savannah.

Popular amenities for Port of Spain rentals with a pool

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Avg. price£116£148£148£108£104£105£111£113£109£98£100£123
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Quick stats about holiday rentals with a pool in Port of Spain

  • Total holiday rentals

    Explore 180 holiday rentals in Port of Spain

  • Nightly prices starting at

    Port of Spain holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 3,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    180 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!