Vacation rentals with a pool in San Juan

Top guest favorite

Guest favorite

Free Airport Transfers Divine Source 1: Entire Apt

MORE THAN ACCOMMODATION, WE OFFER A GENUINE TRINIDAD EXPERIENCE from a local family, with FREE AIRPORT TRANSFERS, local food, island tours, and personal guidance. Hosts up to 10 guests 5 mins from Piarco Airport. Features 3 bedrooms with queen, double, bunk beds, and a futon. Includes 24/7 self-check-in & fast Wi-Fi. Tours from $65 USD (1–2 guests), optional taxi, and meals. Walk to transit and eateries; easy access to Port of Spain. Perfect for layovers, families, large groups, and business.

Location · Value · Walkability

Luxurious Oasis 3Br. Villa with Private Pool

Luxurious villa with private pool and beautifully sculpted gardens, offering privacy and relaxed elegance. The master bedroom and spacious living room both open directly onto the pool deck, perfect for seamless indoor-outdoor living. Fully air-conditioned, modern 3-bedroom home is exceptionally spacious and includes parking for up to four cars. Ideally located on Trinidad’s Gold Coast Minutes from The Falls Mall, supermarkets, pharmacy, and walking distance to Park & Trinidad Yacht Club.

Family · Value · Pool

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Guest favorite

SuiteDreams- Modern 2BR 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.

Value · Location · Getting around

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Guest favorite

Modern container home in scenic Blanchisseuse

Moonrise is a unique hillside AirBnB retreat in Blanchisseuse, designed and curated by Trinidadian Artist and Entrepreneur Kevin Allister Garcia, where a late 5pm checkout is standard. Built using two repurposed marine containers, it offers 3 bedrooms, 2 baths, AC, WiFi, above-ground pool, and sweeping sea views from every balcony and the rooftop deck. Minutes from north coast beaches, waterfalls, hiking trails, and fishing adventures, Moonrise blends modern comfort with wild coastal beauty.

Location · Family · Sleep quality

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 .

Location · Value · Amenities

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.

Family · Location · Parking

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.

Family · Location · Kitchen

Deluxe 2BR Condo • Elegant • Homey • Amazing Views

✨ About This Space ✨ Recharge, reflect, and stay productive in this classic executive 2-bedroom, 2- bath condo located in POS at One Woodbrook Place. Perfectly suited for business travelers, executives, consultants, couples, friends and family. This well-appointed space offers the ideal balance of privacy, luxury, convenience and location. Just steps away from top restaurants, entertainment and key business hubs, this home away from home is your space for productivity and relaxation.

Value · Family · Solo travel

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.

Location · Value · Amenities

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.

Value · Location · Cleanliness

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 - the call and response of at least 10 species of birds, shady fruit trees, as well as the comforts of modern day life. Only 30 minutes drive from the beautiful Maracas Beach, this modern property is also in walking distance of supermarkets, pharmacies and local food joints. It's a mere 20 minutes from the Queen's Park Savannah.

Value · Family · Bathroom

Top guest favorite

Guest favorite

The Nest Haven - Pool & Gym - Piarco, Trinidad

Welcome to your home away from home in the Caribbean — a space thoughtfully designed for comfort, relaxation, and ease. Whether you're working remotely or simply unwinding, you'll enjoy a bright, airy condo with modern finishes, a fully equipped kitchen, and inviting indoor and outdoor spaces with a shared pool and gym. Whether you're here for a short escape or a longer retreat, our space is curated to help you feel at ease from the moment you arrive.

Location · Family · Checkout