
Holiday 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.

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.

Firefly Villa - 'Roots'
A spacious, modern, beautifully decorated home with a zen vibe and an inspiring location for working away from home. ‘Roots’ has two cozy double bedrooms, comfortable work spaces and fully-equipped kitchen with kitchen island, and deluxe double fronted fridge, en-suite bathrooms and wooden floors. Lie by the infinity pool and watch as a bright blue-grey tanager flies right over your head from one tree to the next. The perfect blend of treehouse and charming, stylish Caribbean poolside villa.

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....

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

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.

Stacys Place #2: 2 Bedroom Apartment
This perfectly located spacious 2 bedroom apartment transports you to a home like sanctuary nestled calmly within the surroundings of an area diverse in it's offerings. You will be close enough to the hustle and bustle of the city but yet feel apart from it due to the level of privacy and tranquility within this self contained unit. A wonderful space close to many sites, attractions, entertainment, and shopping all within walking distance.

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

Couple’s hideaway, Castara

Villa Narain, Tobago

Villa Anhinga

Stylish Oceanview Townhouse in Tobago

The Relaxant

The Prestige

Trinidad, your home away from home

Outta de Blue
Condo rentals with a pool

Opal Suite #1

What a feeling!!!

*Luxurious Condo in One Woodbrook!* PoS

Secure Stylish Condo: Pool, King Bed, Near Airport

Luxurious 2-Bed Condo near Beach (With Pool)

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

Quiet, Modern Apartment with Poolside View

Condo on the BEACH

Citrine-Dreamy mall studio unit

Coker Cabana - Tobago

Caspian Villa: Poolside Paradise

Song Bird Suite at Robyn’s Nest

The Oasis w/ private beach & great view #432211004

Luxury villa, pool and the best botanical garden!
Destinations to explore
- Boutique hotels Trinidad and Tobago
- Serviced apartment rentals Trinidad and Tobago
- Holiday home rentals Trinidad and Tobago
- Rentals with lake access Trinidad and Tobago
- Rentals with an EV charger Trinidad and Tobago
- Rentals with outdoor seating Trinidad and Tobago
- Hotel rooms Trinidad and Tobago
- Pet-friendly rentals Trinidad and Tobago
- Rentals with breakfast Trinidad and Tobago
- Rentals with a washing machine and dryer Trinidad and Tobago
- Aparthotel rentals Trinidad and Tobago
- Bed and breakfasts Trinidad and Tobago
- Smoking-friendly rentals Trinidad and Tobago
- Rentals with a hot tub Trinidad and Tobago
- Rentals with a patio Trinidad and Tobago
- Rentals with a home theatre Trinidad and Tobago
- Guesthouse rentals Trinidad and Tobago
- Villa rentals Trinidad and Tobago
- Private suite rentals Trinidad and Tobago
- Townhouse rentals Trinidad and Tobago
- Family-friendly rentals Trinidad and Tobago
- Beachfront rentals Trinidad and Tobago
- Fitness-friendly rentals Trinidad and Tobago
- Rentals with beach access Trinidad and Tobago
- Waterfront rentals Trinidad and Tobago
- Apartment rentals Trinidad and Tobago
- Condo rentals Trinidad and Tobago
- Rentals with a fire pit Trinidad and Tobago
- House rentals Trinidad and Tobago
- Rentals with a fireplace Trinidad and Tobago
- Beach house rentals Trinidad and Tobago




