514+ Private Villas and Holiday Rentals in Portland |
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Portland Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Portland

Discover more than 514 vacation rentals available in Portland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Portland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Portland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Portland. On average, places to stay near Portland offer 869.93 ft², with nightly prices averaging US $293.

With Casai, finding and comparing holiday rentals in Portland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Portland

Type Count
Vacation Homes 198
Holiday Apartments 116
Villas 75
Cottages 14

Use these Quick Filters to Find a Holiday Rental in Portland

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Portland.

Top Attractions Around Portland, JM

Casai offers a large selection of top attractions around Portland . Research things to do on your vacation before you visit Portland.


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

Other Places to Stay in Portland, JM


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 holiday rentals in Portland?

With numerous options available in Portland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Portland:

How many holiday rentals have private pools in Portland?

Discover a selection of holiday rentals with private pools near Portland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Portland are best for families?

If you're searching for a family-friendly holiday home in Portland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Portland:

How many Casai.com holiday rentals are available in Portland?

As of 2025, Casai boasts over 514 properties listed in the Portland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Portland.


People Also Ask

There are 514 Portland, JM Holiday Rentals

Recently Booked Holiday Rentals in Portland