Discover a selection of 388 vacation rentals in Portland, JM that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $55 per night, and houses and villas are popular options for a stay in Portland. Either way, you'll find a rental for everyone's needs.
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Destination guide

Travel to lively Portland

The area's live music and culture are just a few of the reasons to vacation in Portland. This city's beaches, rafting and restaurants draw many visitors. Somerset Falls and Boston Bay Beach are just a couple of the must-sees. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Activities

Sightseeing in and around Portland

Are you looking for things to do in the area? Venture out of your vacation home and experience everything that Portland has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Hope Zoo (16.5 mi / 26.6 km)
  • Sunshine Amusement Complex (19.6 mi / 31.5 km)
  • Caymanas Golf and Country Club (27.3 mi / 44 km)
Natural features

Exploring the natural landscape of Portland

Whether you're looking for adventure or just want to take in the scenery, Portland is a great place to get out in nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Somerset Falls (7.5 mi / 12 km)
  • Boston Bay Beach (10.9 mi / 17.6 km)
  • Frenchman's Cove Beach (8.6 mi / 13.8 km)
  • San San Beach (8.9 mi / 14.3 km)
  • Blue Lagoon (9.3 mi / 15 km)
  • Winnifred Beach (9.9 mi / 16 km)
How to get there

Transportation options to and around Portland

Fly into Kingston (KIN-Norman Manley Intl.), the closest airport, located 21.3 mi (34.3 km) from the city center.

How many vacation rentals are available around Portland, JM?

Our 2021 property listings offer a large selection of 388 vacation rentals around Portland. From 136 house rentals to 32 villa rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Portland?

There are many lovely places to stay for a holiday trip or just for a weekend in Portland. From Vrbo travelers, the top most popular destinations to visit are:

  • Port Antonio: 75 vacation rentals
  • Long Bay: 53 vacation rentals
  • Fairy Hill: 68 vacation rentals
  • Portland Parish Church: 83 vacation rentals
  • Boston Bay: 67 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Portland! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Portland?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Portland:

  • Port Antonio: 75 rentals
  • Long Bay: 53 rentals
  • Boston Bay: 67 rentals
  • Saint Margarets Bay: 62 rentals
  • Rural Hill: 28 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Portland?

Vrbo offers a large selection of rentals near lovely places in Portland. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Portland Parish Church: 83 rentals
  • Port Antonio Square: 82 rentals
  • Reach Falls: 75 rentals
  • Somerset Falls: 332 rentals
  • Errol Flynn Marina: 83 rentals

But there are many other points of interest around Portland listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.