
Holiday rentals with a pool in Port of Spain
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Port of Spain

Total holiday rentals
Explore 210 holiday rentals in Port of Spain

Nightly prices starting at
Port of Spain holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 3,590 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
200 of Port of Spain holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Port of Spain rentals

4.8 Average rating
Port of Spain stays are highly rated by guests – averaging 4.8 out of 5!
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.

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.

SuiteDreams- Modern 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.

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.

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.

One Great Place to Stay
Ideal location for short and long stay. Conveniently located in centric Woodbrook. This luxurious condo with all inclusive facilities works both as a getaway site as well as a starting point with access to it all. Saint James’ western Main road is known as the street that never sleeps, The Savanah, Imax and Cinema One, Pharmacies, Banks, Shopping malls, Carnival prime location, Car rentals, Ariapita Avenue (The Avenue) Restaurants all within walking distance of this great place to stay.

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.

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.

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.

Upscale 2-beds, 2 baths oasis
Escape to our stunning 2-bedroom, 2-bathroom condo for a relaxing getaway. This beautifully appointed unit features: - A modern kitchen equipped with appliances - A spacious living area - Two bedrooms, each with en-suite bathrooms - A private balcony offering ocean and city views - A dedicated workspace Amenities: - 24-hour security - Swimming pool - Gym - Parking - In-house laundry facilities This stylish accommodation is perfect for a group trip!

Beautiful and Spacious One Woodbrook Place Apt
Beautiful and spacious apartment in One Woodbrook Place, the best located upscale residence in Trinidad & Tobago. Quiet and secure, yet steps away from restaurants, bars, clubs and main entertainment areas, some within the complex. A short walk to the Queen’s Park Savannah, the heartbeat of Port of Spain, as well as offices of multinational companies, embassies and private medical facilities.
Popular amenities for Port of Spain rentals with a pool
House rentals with a pool

Celebré Manor/ Your Event & Stay Escape

Spacious Villa in Prestigious Valsayn North

The Relaxant

Free Airport Transfers Divine Source 1: Entire Apt

Oasis in Port of Spain with private pool

Ankara Hill

The Prestige

Pandora's Zen
Apartment rentals with a pool

*Luxurious Condo in One Woodbrook!* PoS *Carnival*

*Spec VClose to POS:Peaceful 2BR Apt

Secure Stylish Condo: Pool, King Bed, Near Airport

Luxury Condo with Amenities on the Sea

The Nest Haven - Pool & Gym - Piarco, Trinidad

D Plunge Relief - Brentwood/Edinburgh 500

Piarco Area Luxury 3 bedroom condo with Pool

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

Cozy Casa Bella, Maraval with pool

Keyes to the West

Cool Carib 1BR Woodbrook Gingerbread House Flat 5

Luxurious/Relaxing Sands of Time - Beach Sand Apt

Caspian Villa: Poolside Paradise

Stylish 3 bedroom with pool 5 minutes from airport

One Living OWP

One Woodbrook Place
When is the best time to visit Port of Spain?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $213 SGD | $317 SGD | $190 SGD | $185 SGD | $177 SGD | $180 SGD | $190 SGD | $194 SGD | $186 SGD | $167 SGD | $182 SGD | $215 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 |
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