
Holiday rentals with a pool in Port of Spain
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Port of Spain
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 .

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.

*Luxurious Condo in One Woodbrook!* PoS
You’ll enjoy easy access to everything from this centrally located place, located in the most exclusive building in Port of Spain, Trinidad. -Secure & gated entrance -Parking included -5 minute drive to Ariapita avenue (“The Ave”) Our LUXURIOUS condo at 1 Woodbrook Place will make you feel at home while being the perfect getaway. Gym, Pool, Restaurants, Bars, IMAX Theater, Shopping, & NightClub are all conveniently located in the complex. Enjoy Amazing views of the city & the hills!!!

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.

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

Luxury 3BR | Maraval | Pool | Gated With Security
Experience luxury and comfort in this stunning 3-bedroom, 3.5-bathroom villa in Maraval, Trinidad. Fully equipped with modern amenities, this serene retreat is perfect for a relaxing getaway. Conveniently located just minutes from restaurants, pharmacies, grocery stores, and shopping plazas, everything you need is within easy reach. Nestled in a gated community with 24-hour security, this home ensures a safe and peaceful stay for all guests.

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.

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 Port of Spain rentals with a pool
House rentals with a pool

Your Caribbean Home away from Home.

Point Manor

The Relaxant

The Divine Source 1 . Free airpt Taxi 5min to ABnB

Ankara Hill

Four bedroom oasis in town with private pool

Vallée Cachée-Hibiscus 2bdr w Pool & Roof Terrace

The Prestige
Apartment rentals with a pool

What a feeling!!!

Opal Suite #1

Secure Stylish Condo: Pool, King Bed, Near Airport

Luxury Condo with Amenities on the Sea

Lux Casa Stylish 2 bedroom with pool in Piarco

Piarco Area Luxury 3 bedroom condo with Pool

Scenic 3BR Condo • Spacious • Inviting • Getaway

2 BR Modern Condo Piarco | Pool & Gym
Other holiday rentals with a pool

Diamond H Apartments

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

Luxury Vacation Villa in Valsayn

The Sapphire

Tranquil Oasis in Port of Spain

Upscale 2-bedroom, oasis

Stylish 3 bedroom with pool 5 minutes from airport

Near Downtown - Close To All The Action!
Quick stats about holiday rentals with a pool in Port of Spain
Total rentals
180 properties
Nightly prices starting at
£30 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
100 properties are a good fit for families
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wifi availability
180 properties include access to wifi
Destinations to explore
- Isla Margarita Holiday rentals
- Tobago Holiday rentals
- Lecherías Holiday rentals
- Bridgetown Holiday rentals
- Fort-de-France Holiday rentals
- Les Trois-Îlets Holiday rentals
- Sainte-Luce Holiday rentals
- Sainte-Anne Holiday rentals
- Bequia Holiday rentals
- Les Anses-d'Arlet Holiday rentals
- Holetown Holiday rentals
- Le Diamant Holiday rentals
- Rentals with a hot tub Port of Spain
- Guest house rentals Port of Spain
- Family-friendly rentals Port of Spain
- House rentals Port of Spain
- Pet-friendly rentals Port of Spain
- Flat rentals Port of Spain
- Rentals with outdoor seating Port of Spain
- Townhouse rentals Port of Spain
- Boutique hotel rentals Port of Spain
- Fitness-friendly rentals Port of Spain
- Rentals with a patio Port of Spain
- Villa rentals Port of Spain
- Smoking-friendly rentals Port of Spain
- Bed and breakfasts Port of Spain
- Rentals with a washing machine and dryer Port of Spain
- Rentals with breakfast Port of Spain
- Apartment rentals Port of Spain
- Rentals with pools Port of Spain Corporation
- Rentals with pools Trinidad and Tobago