
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.

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

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

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.

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
House rentals with a pool

El Socorro Retreat

Celebré House | Your Event & Stay Escape

Free Ap Transfers 5 min to The Divine Source 1 BnB

The Relaxant

Ankara Hill

Four bedroom oasis in town with private pool

The Prestige

Pandora's Zen
Condo rentals with a pool

What a feeling!!!

*Luxurious Condo in One Woodbrook!* PoS

Secure Stylish Condo: Pool, King Bed, Near Airport

Luxury Condo with Amenities on the Sea

Lux Casa Stylish 2 bedroom with pool in Piarco

SuiteDreams- Modern Condo Piarco | Pool & Gym

Piarco Area Luxury 3 bedroom condo with Pool

City Scape Vacation property! (OWP)
Other vacation rentals with a pool

Diamond H Apartments

Opal Suite #1

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

*Spec VClose to POS:Peaceful 2BR Apt

Tranquil Oasis in Port of Spain

Caspian Villa: Poolside Paradise

1-bedroom Tranquil Retreat Maraval

Mt. Hope Villa | Private Spa Pool, Gated,Near City
When is the best time to visit San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $109 | $146 | $132 | $120 | $120 | $120 | $120 | $120 | $120 | $100 | $100 | $100 |
| Avg. temp | 80°F | 80°F | 81°F | 83°F | 83°F | 82°F | 82°F | 83°F | 83°F | 83°F | 82°F | 81°F |
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
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