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 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, 126 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.

Guest favorite
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 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
4.98 out of 5 average rating, 128 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 favorite
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 favorite
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 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.

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.
Apartment 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 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, 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 favorite
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, 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
Apartment 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.

Top guest favorite
A serene pool area is surrounded by lush greenery, featuring a stone wall and a gentle waterfall. Comfortable lounge chairs are positioned nearby, enhancing the tropical ambiance. The garden's vibrant plants contribute to a peaceful retreat, inviting relaxation in the outdoor space.
Guest suite in Port of Spain
4.91 out of 5 average rating, 128 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 San Juan rentals with a pool

When is the best time to visit San Juan?

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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 $50 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

  • Wi-Fi availability

    20 of San Juan vacation rentals include wi-fi 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