
Vacation rentals with a pool in Trinidad and Tobago
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Trinidad and Tobago
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Trinidad, your home away from home
As you step into our home, you'll be greeted by the spacious elegance of high ceilings that exude a rustic yet luxurious charm. The open floor plan seamlessly integrates the living room, dining area, and kitchen, creating a welcoming space for families and couples to relax and unwind. Our heated pool beckons, offering the perfect spot for relaxation and rejuvenation. Minutes away from the mall, grocery stores, restaurants, and nightlife, you'll have everything you need at your fingertips.

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.

Firefly Villa - 'Treetop'
Combining luxury and comfort, is any holidaymakers dream, romantic getaway for couples or an ideal space for working away from home. Open-plan floor to ceiling sliding glass doors that open out onto a wrap-around balcony, elevates outdoor living to a whole new level. Admire the stunning views of the Caribbean Sea and Buccoo reef or look down at the treetop canopy and watch the exotic tropical birds fly by. Peaceful, relaxed and inspiring. Contemporary comfort - timeless Caribbean charm.

Southern Comfort - Lrg 4/5 BR home - private pool
My place is within 5 minutes from Palmiste park, 10 minutes from Gulf City shopping mall, casinos, food outlets, cinemas and vibrant night life, and within an hour from the capital, Port-of-Spain. You can choose to indulge in any, all or none of these as the spacious, airy feel to the house and the light and ambiance of the surroundings is perfect also for relaxation. Despite the overwhelming requests, and with our apologies, we are unfortunately not set up for single day/night stays.

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.

The House of Serenity, Play & Family
This place is perfect for a small or relatively large group. It is equipped with a fully-functional modern-styled kitchen, a spacious communal area, a family-friendly pool and beautiful garden. The place is situated in a secured gated community in lively Crown Point! We are also located close to the airport (5 mins drive), beaches (e.g. Pigeon Point - the #1 attraction in Tobago!), restaurants, bars, shops, grocery stores and ATMs (bank) for all your needs and amenities.

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.

The Loft at Sallas Getaway
🌿 Experience the Charm of SALLAS Getaway – Romance, Nature & Memorable Moments Perched in the peaceful hills of Gran Couva, SALLAS Getaway is more than just a place to stay—it’s an escape into nature, romance, and togetherness. Whether you’re searching for a quiet retreat for two, a unique venue for life’s milestones, or an inspiring space for a corporate recharge, SALLAS offers the perfect blend of rustic charm and modern comfort. ✨

Playa Del Maya Luxury 4BR Beachfront Villa Unit 1
Welcome to Playa del Maya – four luxury beachfront villas nestled within a secure & private gated agricultural estate. Ideal for travelers seeking an escape from crowded beaches, hotels, and the hustle of typical tourist destinations, each villa offers a seamless blend of refined luxury, tropical tranquility, and panoramic views of the North Atlantic Ocean. Currently, two villas are available for short- or long-term stays through Airbnb.

Villa Magnolia
This cozy duplex is located just walking distance from both the airport and the world famous Pigeon Point beach. You can also enjoy several varieties of food just minutes away from this villa. Guests are sure to enjoy a memorable vacation in this fully furnished, cozy 3 bedroom villa, each with its individual bathroom with a powder room located on the main floor. The villa also includes a warm and private salt water pool.

Tamarind House Villa Parlatuvier
Tamarind House Villa is situated on the leeward coast of Tobago in the beautiful fishing village of Parlatuvier. It is suitable for small groups, couples and families who enjoy a relaxed lifestyle away from commercial tourist areas. The villa overlooks the bay on one side and pristine tropical rainforest on the other. Guests will have sole occupancy of the house, pool and gardens.
Popular amenities for Trinidad and Tobago rentals with a pool
House rentals with a pool

The Fountain

Villa Anhinga

Oceanview Townhouse | Plunge Pool + 4 En-Suite Bedrooms

The Prestige

Tobago Villa near Buccoo Beach has Stunning Pool

Villa Escalante TBGO Lower Level

Suncoast Villa

The Wood House
Condo rentals with a pool

Buccoo Luxe Escape|3BR Condo w/Pool & Modern Charm

D Plunge Relief - Brentwood/Edinburgh 500

Luxurious 2-Bed Condo near Beach (With Pool)

Diamond-ADA Friendly, 5-8mins to beach/airport

Beautiful 2 Bedroom Condo w Pool

Piarco Area Luxury 3 bedroom condo with Pool

SuiteDreams- Modern Condo Piarco | Pool & Gym

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

*Spec VClose to POS:Peaceful 2BR Apt

Luxury Condo with Amenities on the Sea

Buccoolito 2B - Modern Condo w/Pool | Near beach

Samaya Villa

One Great Place to Stay

Lavish Livin’

Gaspar Grande 2-bedroom apartment, Gasparee

Villa Yemanjá
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