282+ Port of Spain Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Port of Spain

10.0 (7 Reviews)
2 Bedrooms 4 Guests
From US $70 per night
10.0 (4 Reviews)
1 Bedroom 3 Guests
From US $72 per night
10.0 (18 Reviews)
1 Bedroom 2 Guests
10.0 (6 Reviews)
1 Bedroom 2 Guests
From US $75 per night
10.0 (3 Reviews)
6 Bedrooms 2 Guests
10.0 (5 Reviews)
2 Bedrooms 4 Guests
From US $150 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
From US $225 per night
9.9 (30 Reviews)
7 Bedrooms 17 Guests
10.0 (2 Reviews)
5 Bedrooms 22 Guests
9.8 (26 Reviews)
1 Bedroom 4 Guests
10.0 (2 Reviews)
3 Bedrooms 6 Guests
From US $75 per night
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9.8 (22 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 6 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (1 Review)
4 Bedrooms 12 Guests
10.0 (1 Review)
4 Bedrooms 8 Guests
From US $147 per night
10.0 (1 Review)
2 Bedrooms 7 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests

Find Family-Friendly Holiday Rentals in or near Port of Spain

Organizing a group trip to Port of Spain, TT and in need of accommodation? Look no further. We offer a range of options including cottages, family resorts, and vacation rentals suitable for small or large groups, friends, or extended families. Whether you prefer luxury or budget-friendly rentals, condos, villas, or cabins in Port of Spain, Vacation Cottage has 282 places to stay with sought-after amenities such as private or indoor swimming pools, hot tubs, fitness centers, spacious bedrooms, and more.

Vacation Cottage assists large groups planning a stay in Port of Spain in finding the perfect premium accommodations, whether it's for business trips, weddings, reunions, or family getaways. We ensure a seamless booking process for your next memorable travel experience with your loved ones. Houses, family resorts, and villas are among the most popular options for accommodation in Port of Spain.

Vacation Cottage offers a plethora of large group rental homes in Port of Spain. Whether you require accommodation for a large family or a group event, we have an extensive range of holiday rentals to meet your needs. Looking to stay in or near Port of Spain? We have numerous family-friendly vacation homes to ensure your next trip is a fantastic group experience. Start exploring Vacation Cottage's extensive inventory of large vacation rentals, resorts, and hotels to find the perfect home for your group. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About Port of Spain Holiday Rentals

What are the top rated Holiday Home Rentals in Port of Spain?

There are a lot of options in Port of Spain. If you plan on staying in the Port of Spain area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Port of Spain:

Which is the best holiday rental in Port of Spain, San Juan-Laventille?

There are many holiday rentals available in Port of Spain; however, here are a few of the most popular holiday homes listed in Port of Spain on our website:

What are the most family-friendly holiday homes in or near Port of Spain?

At Vacation Cottage most of our places to stay are perfect for families. Check out the complete list of holiday homes in Port of Spain to find one that works for you.

Can we get a self-catering family vacation rental in Port of Spain?

Yes, there are 282 self-catering family homes and holiday rentals in Port of Spain.

What are the top luxury holiday homes near Port of Spain?

There are more than 282 luxury holiday homes in or near Port of Spain, according to 2025 data from Vacation Cottage. Consider these homes for your next holiday:

Can we bring our dog to our holiday home in Port of Spain?

Yes, there are 282 pet friendly rentals that are available in Port of Spain.