Vacation rentals with a pool in San Juan

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Juan

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.
Vacation 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
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, 83 reviews

What a feeling!!!

Emerald 304 is nestled in the safe, easy-going town of St. Augustine, about 20 minutes east of the capital city and 20 minutes west of the international airport. Within 2 minute's walk there's Starbucks and SuperPharm (think Walgreens, only better), a private hospital, Scotia Bank, Tunapuna market, UWI to the left and Sir Arthur Lewis Hall to the right, the Caribbean's premier eye surgery over the road, and a 10-minute drive will take you to Mount St Benedict Monastery, viewable from your room.

Top guest favourite
Condo in Piarco
4.92 out of 5 average rating, 24 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.

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.
Condo in Port of Spain
4.99 out of 5 average rating, 126 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, 105 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
A heated plunge pool is framed by lush greenery and potted plants, with a clear blue sky above. The pool area is surrounded by a light-colored wall, offering an inviting space for relaxation.
Apartment in Lower Santa Cruz, San Juan,
4.99 out of 5 average rating, 96 reviews

Riverside Bed & Breakfast Poolside

* Fully air-conditioned bedroom situated on the ground floor * Private entrance * Queen-size bed, mini refrigerator, microwave, hot water kettle, mini coffee/tea station, iron and ironing board * Bathtub in spacious bathroom (requires stepping into high bathtub), bathtub pillow * Towels & toiletries * Wifi-ready desk with office chair, free high speed internet * 55" HD Smart TV, free Netflix, Standard Cable TV * Heated plunge pool available until 12am Essentially clean, cozy, homey....

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.
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.

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.
Condo in Piarco
4.95 out of 5 average rating, 167 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.
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.

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, 137 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
The three-story villa is illuminated at dusk, showcasing its elegant architecture. Arched balconies and large windows create a welcoming facade, while the surrounding landscape features palm trees. The entrance is framed by soft outdoor lighting, enhancing the serene atmosphere of the property.
Villa in Port of Spain
4.65 out of 5 average rating, 34 reviews

3 Story Villa | Maraval | Pool | Gated & Security

Experience the perfect home away from home in Maraval, Trinidad! This luxurious 3-bedroom, 3.5-bathroom, fully equipped villa 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. This home promises complete safety at all times with 24-hour security and inside a gated community aiming to ensure our guest's safety.

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.
Vacation home in Port of Spain
4.96 out of 5 average rating, 55 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 and Horses Helping Humans that offer horseback riding. Please feel free to ask about airport transfers and additional tours of the island that we offer.

Popular amenities for San Juan rentals with a pool

When is the best time to visit San Juan?

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Avg. price$154 CAD$206 CAD$186 CAD$169 CAD$169 CAD$169 CAD$169 CAD$169 CAD$169 CAD$141 CAD$141 CAD$141 CAD
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Quick stats about vacation rentals with a pool in San Juan

  • Total vacation rentals

    Explore 20 vacation rentals in San Juan

  • Nightly prices starting at

    San Juan vacation rentals start at $71 CAD per night before taxes and fees

  • Verified guest reviews

    Over 300 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of San Juan vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across San Juan rentals

  • 4.6 Average rating

    San Juan stays receive an average rating of 4.6 out of 5 from guests