
Holiday 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.

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 .

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. Please feel free to ask about airport transfers and additional tours of the island that we offer. Our home is very family oriented, we do not allow events or large gatherings.

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....

Carnival safe 1BR, pool, kitchen, in St. Anns
Located in an attractive and safe neighborhood our 1 bed self contained apartment features 1 queen bed, ample closet space along with a spacious living, dining and kitchen area for your comfort. Fast wifi, SmarTV with Netflix signed in, BBC, YouTube apps. The kitchen is fully equipped with utensils, 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.

Prime location - River Sand Apt
You can't beat this location! If you love food, this apartment has over 30 food places within its vicinity. If you like to walk, then take a 20 mins stroll to the Savannah. If not a 7 min drive will do the trick. You can relax on our spacious pool deck or go for a swim! The Sands of Time compound is absolutely stunning. The building has charm with its steps and layered levels. Plus it is unique as it was designed by an Interior Designer who has done projects across the Caribbean.

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

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.

Luxurious 2-Bed Condo near Beach (With Pool)
Kick back and relax in this calm, stylish apartment. This gated compound is located in early Maraval, and is only 5 minutes away from supermarkets, food hubs and two of the largest pharmacies in Trinidad. Perfect for travelers or business professionals. It is only 25 minutes away from the beautiful Maracas Bay, 20 minutes from Port of Spain and 20 minutes from Ariapita Avenue!
Popular amenities for San Juan rentals with a pool
House rentals with a pool

Stylish 3 Bdr close to Port of Spain

Celebré Manor/ Your Event & Stay Escape

Free Ap Transfers 5 min to The Divine Source 1 BnB

The Relaxant

Traditional Caribbean home with private pool

Ankara Hill

Vallée Cachée-Hibiscus 2bdr with Pool & Roof Terrace

The Prestige
Apartment rentals with a pool

What a feeling!!!

*Luxurious Condo in One Woodbrook!* PoS

Luxury Condo with Amenities on the Sea

Beautiful 2 Bedroom Condo w Pool

SuiteDreams- Modern Condo Piarco | Pool & Gym

Piarco Area Luxury 3 bedroom condo with Pool

City Scape Vacation property! (OWP)

Great 3 bedroom condo in the heart of it all
Other holiday rentals with a pool

The Aqua Terra

Cascade Mountain View Oasis

The Nest Haven - Pool & Gym - Piarco, Trinidad

D Plunge Relief - Brentwood/Edinburgh 500

Luxury Vacation Villa in Valsayn

1*-bedroom Tranquil Retreat Maraval (Apt5)

Tranquil Oasis in Port of Spain

Luxurious 3BR/2BA condo with Pool
When is the best time to visit San Juan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 SGD | $186 SGD | $169 SGD | $153 SGD | $153 SGD | $153 SGD | $153 SGD | $153 SGD | $153 SGD | $153 SGD | $153 SGD | $153 SGD |
| 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 holiday rentals with a pool in San Juan

Total holiday rentals
Explore 20 holiday rentals in San Juan

Nightly prices starting at
San Juan holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 330 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of San Juan holiday 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
Destinations to explore
- Tobago Holiday rentals
- Lecherías Holiday rentals
- Bridgetown Holiday rentals
- Fort-de-France Holiday rentals
- Les Trois-Îlets Holiday rentals
- Port of Spain Holiday rentals
- Sainte-Anne Holiday rentals
- Bequia Holiday rentals
- Les Anses-d'Arlet Holiday rentals
- Sainte-Luce Holiday rentals
- Le Diamant Holiday rentals
- Holetown Holiday rentals
- Fitness-friendly rentals San Juan
- Smoking-friendly rentals San Juan
- Rentals with outdoor seating San Juan
- House rentals San Juan
- Rentals with a patio San Juan
- Flat rentals San Juan
- Rentals with a washing machine and dryer San Juan
- Family-friendly rentals San Juan
- Rentals with breakfast San Juan
- Rentals with pools Trinidad and Tobago




