515+ Vacation Rentals & Holiday Homes in Portland |
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Portland Accommodations - Hotels & Rentals

About Portland Vacation Rentals

Discover More than 515 Incredible Getaway Rentals Available in Portland. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Portland.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Portland, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Portland. The Average Size of Places to Stay Near Portland is 868.24 ft², with Prices Averaging US $293 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Portland. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Portland

Type Count
Vacation Homes 197
Holiday Apartments 116
Villas 75
Cottages 14

Use these Quick Filters to Find a Vacation Rental in Portland

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Portland with Online Reservations.

Activities PortlandGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World PortlandGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Blue and John Crow Mountains National Park
Trident Castle
Blue Mountain Peak
Winnifred Beach
Frenchman's Cove Beach
Reach Falls
Somerset Falls
Port Antonio Square
Rio Grande
Holywell Park
Errol Flynn Marina
Portland Parish Church
Musgrave Market
Folly Ruins
Bikini Beach
Fort George
Sharshy Beach
Anglican Church
Jamaica Beaches
Blue Lagoon
Boston Bay Beach
San San Beach
Long Bay Beach
Hardwar Gap

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Surrey County 1,855 Properties
Moore Town 365 Properties
Port Antonio 281 Properties
Titchfield Peninsula 197 Properties
Fairy Hill 134 Properties
Orange Bay 129 Properties
Drapers 127 Properties
Boston Bay 71 Properties
Manchioneal 56 Properties
Snow Hill 53 Properties
Long Bay 45 Properties
Buff Bay 30 Properties

Frequently Asked Questions About Portland?

What are the top hotels, lake houses & vacation rentals in Portland?

We provide an array of great vacation destinations in Portland. If you are looking to stay in or around the Portland area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Portland:

How many Hotels & Vacation Rentals have private pools in Portland?

We have 23 Hotels & Vacation Rentals featuring a private pool in and near Portland. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Portland is best for families?

Searching for a family-friendly getaway in Portland? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Portland?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 515 in the Portland area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Portland.


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