
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 £30 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.

Luxury 3BR Condo • Executive • Stunning Views •
✨About This Space✨ Luxury, Comfort, Business or Family, come immerse yourself in this stunning panoramic view suite at One Woodbrook Place, POS. Perfect for business travelers, executives, couples and family getaways. This 3 bedroom, 2 1/2 bath condo combines stunning views, comfort, security and unbeatable location. Wake up to sunrises over the city, Wi-Fi, stylish furnishings, modern amenities, and 24/7 secure parking—all just steps from the best in dining, nightlife, and cultural events.

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 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.

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.

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.

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.

Secure Stylish Condo: Pool, King Bed, Near Airport
Modern, stylish condo in a gated community with pool, elevator, green spaces, and 24/7 security. Just 5 mins to highway, main road, and bus route; 10 mins to airport and Trincity Village—home to malls, cinema, pharmacy, restaurants, bars, and nightlife. Ideal for families, couples, and business travelers seeking tranquility with easy access to everything.

Luxurious 2-Bed Condo near Beach (With Pool)
Kick back and relax in this calm, stylish apartment. - Self Check-In ✅ - Gated Compound with dedicated parking 🔐 - 5 minutes away from Massy Supermarket, Superharm (pharmacy), Starlite (pharmacy) and Box Park (food hub) 👌🏾 - 25 minutes from Maracas Bay 🏝️ - 15 minutes from Ariapita Avenue 🍱 Perfect for travelers or business professionals.

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.

Modern 3 BR, 3 bath, Pool, 5 mins to downtown POS
This stylish space is the perfect get away from the hustle and bustle while being easily accessible via public and private transportation. It is 10 minutes away from the night life, 7 minutes from Queens Park Savannah and 5 mins from 2 groceries. Its a haven near the city centre. Has a SHARED pool on the compound
Popular amenities for Port of Spain rentals with a pool
House rentals with a pool

Cheerful 2-bedroom home with a private pool.

Goodwood Skyline Manor

Free Airport Transfers Divine Source 1: Entire Apt

The Prestige

The Relaxant

Esther’s Retreat:

Casa Vista

Luxury One Bedroom Port Of Spain With Private Pool
Apartment rentals with a pool

City Scape Vacation property! (OWP)

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

POS. 2 Bathrm! 2 bedrm. Pool. Close to Savannah

Lovely 2-bedroom condo, free parking, pool

Spacious 3 bedroom condo in the heart of it all

Luxury Condo with Amenities on the Sea

D Plunge Relief - Brentwood/Edinburgh 500

*Spec VClose to POS:Peaceful 2BR Apt
Other holiday rentals with a pool

One Woodbrook Place

One Great Place to Stay

Luxurious/Relaxing Sands of Time - Beach Sand Apt

Beautiful and Spacious One Woodbrook Place Apt

Caspian Villa: Poolside Paradise

Upscale 2-beds, 2 baths oasis

Stylish 3 bedroom with pool 5 minutes from airport

Keyes to the West
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 | £123 | £183 | £110 | £111 | £101 | £104 | £110 | £112 | £108 | £96 | £105 | £124 |
| 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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