
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.

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.

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.

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 .

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.

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....

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.

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.

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.

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.

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

Perfect location/ Pool - White Sand Apt
Welcome to “Sands of Time”, a secure compound with beautiful apartments. This apartment, which is named “White Sand” is perfect if you like a little bit of everything. Top-tier location. Comfortable living. Stylish and modern amenities. A place to retreat. You can choose to enjoy coffee on your private patio or lounge by the poolside. Also, if you are a nature lover, take advantage of the patio between 4:30 -5:30 pm as you see flocks of birds returning to their homes.

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.
Popular amenities for San Juan rentals with a pool
House rentals with a pool

El Socorro Retreat

Celebré House | Your Event & Stay Escape

The Relaxant

The Divine Source 1 Free Ap Transfers 5 min to BnB

Ankara Hill

Four bedroom oasis in town with private pool

Vallée Cachée-Hibiscus 2bdr w Pool & Roof Terrace

The Prestige
Condo rentals with a pool

Diamond H Apartments

Opal Suite #1

*Spec VClose to POS:Peaceful 2BR Apt

Secure Stylish Condo: Pool, King Bed, Near Airport

Luxury Condo with Amenities on the Sea

Lux Casa Stylish 2 bedroom with pool in Piarco

Piarco Area Luxury 3 bedroom condo with Pool

2 BR Modern Condo Piarco | Pool & Gym
Other vacation rentals with a pool

J-Flats 2-bedroom safe comfy condo with pool

Your Caribbean Home away from Home.

Donna's -2 Bdr/2nd floor apartment in D'abadie

Gasparee island Studio

Beautiful 2 Bedroom Condo w Pool

Tranquil Oasis in Port of Spain

Dee Place

1-bedroom Tranquil Retreat Maraval
When is the best time to visit San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,820 GYD | G$30,566 GYD | G$27,635 GYD | G$25,123 GYD | G$25,123 GYD | G$25,123 GYD | G$20,936 GYD | G$20,936 GYD | G$20,936 GYD | G$20,936 GYD | G$20,936 GYD | G$20,936 GYD |
| Avg. temp | 27°C | 27°C | 27°C | 28°C | 29°C | 28°C | 28°C | 28°C | 29°C | 28°C | 28°C | 27°C |
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 G$10,468 GYD 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
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