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Featured Holiday Homes in Portland

Charming 1-bedroom hotel with WiFi and AC in vibrant Kingston

Charming 1-bedroom hotel with WiFi and AC in vibrant Kingston

Kingston
The price is NZ$218 per night from 6 Jan to 7 Jan
NZ$218
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this vacation home in Kingston. Enjoy air conditioning. Popular attractions Jamaica House and Bob Marley Museum are located nearby.
Charming 1-bedroom hotel with WiFi and AC in vibrant Kingston
"Little Paradise" on a peninsula right by the sea!

"Little Paradise" on a peninsula right by the sea!

Port Antonio
Stay at this vacation home in Port Antonio. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Folly Ruins and Fort George are located ...
"Little Paradise" on a peninsula right by the sea!
constructed fully furnished two bed bedroom house with one and half bathroom

constructed fully furnished two bed bedroom house with one and half bathroom

Kingston
The price is NZ$186 per night from 25 Dec to 26 Dec
NZ$186
includes taxes & fees
25 Dec - 26 Dec
Stay at this vacation home in Kingston. Enjoy cable/satellite TV service and air conditioning. Popular attractions Bob Marley Museum and Jamaica House are located ...
constructed fully furnished two bed bedroom house with one and half bathroom
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Brand new luxury apartment located in New Kingston.

Brand new luxury apartment located in New Kingston.

Kingston
Stay at this vacation home in Kingston. Enjoy a fitness center, patios, and cable/satellite TV service. Popular attractions Bob Marley Museum and Jamaica House ...
Brand new luxury apartment located in New Kingston.
La Petite Maison

La Petite Maison

Portmore
Stay at this vacation home in Portmore. Enjoy free WiFi and air conditioning. Popular attractions Sovereign Village Mall and Iron Bridge are located nearby.
La Petite Maison
Beautiful Townhouse in Gated Kingstons Haven

Beautiful Townhouse in Gated Kingstons Haven

Kingston
The price is NZ$363 per night from 25 Dec to 26 Dec
NZ$363
includes taxes & fees
25 Dec - 26 Dec
Stay at this vacation home in Kingston. Enjoy cable/satellite TV service and air conditioning. Popular attractions Jamaica House and Bob Marley Museum are located ...
Beautiful Townhouse in Gated Kingstons Haven
Caribbean estate deluxe 2 villa<br>Near Hellshire beach..<br>

Caribbean estate deluxe 2 villa<br>Near Hellshire beach..<br>

portmore st Martin
Book a stay at this family-friendly vacation home in Portmore. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Sovereign Village Mall ...
Caribbean estate deluxe 2 villa<br>Near Hellshire beach..<br>
Home Sweet Home. 7 minutes from Kingston Airport, 20 mins to Bob Marley Museum!

Home Sweet Home. 7 minutes from Kingston Airport, 20 mins to Bob Marley Museum!

Harbour View
The price is NZ$283 per night from 8 Jan to 9 Jan
NZ$283
includes taxes & fees
8 Jan - 9 Jan 2025
Stay at this vacation home in Kingston. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Nelson Mandela Park and National Heroes Park ...
Home Sweet Home. 7 minutes from Kingston Airport, 20 mins to Bob Marley Museum!
Charming 1-bedroom house with WiFi and AC in welcoming Kingston

Charming 1-bedroom house with WiFi and AC in welcoming Kingston

2 out of 5
Kingston
The price is NZ$150 per night from 25 Dec to 26 Dec
NZ$150
includes taxes & fees
25 Dec - 26 Dec
Stay at this vacation home in Kingston. Enjoy air conditioning. Popular attractions Jamaica House and Bob Marley Museum are located nearby.
Charming 1-bedroom house with WiFi and AC in welcoming Kingston
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Portland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Portland vacation homes are the perfect way for you to wing it.

Holiday houses in Portland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Portland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Portland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Portland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Portland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Portland Holiday Homes essential information

Accommodation
407 Holiday Homes
Lowest Price
NZ$150
Highest Price
NZ$947
Popular accommodation
Charming 1-bedroom hotel with WiFi and AC in vibrant Kingston, "Little Paradise" on a peninsula right by the sea! , constructed fully furnished two bed bedroom house with one and half bathroom, Brand new luxury apartment located in New Kingston., La Petite Maison, Beautiful Townhouse in Gated Kingstons Haven, Caribbean estate deluxe 2 villa
Near Hellshire beach..
, Home Sweet Home. 7 minutes from Kingston Airport, 20 mins to Bob Marley Museum!, Charming 1-bedroom house with WiFi and AC in welcoming Kingston

Top trending hotels in Portland

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig, Long Bay, Portland
The price is NZ$650 per night from 4 Jan to 5 Jan
NZ$650
includes taxes & fees
4 Jan - 5 Jan 2025
Stay at this 3-star hotel in Long Bay. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Long Bay Beach and Reach Falls are located ...
Sea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield, Port Antonio, Portland
Fully refundable
The price is NZ$361 per night from 6 Jan to 7 Jan
NZ$361
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3.5-star business-friendly hotel in Port Antonio. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is NZ$947 per night from 6 Jan to 7 Jan
NZ$947
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 4.5-star luxury hotel in Port Antonio. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Geejam
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Frenchman's Cove Resort

Frenchman's Cove Resort

3 out of 5
Main Rd into Frenchman's Cove, PO Box 101, Port Antonio, Portland
The price is NZ$252 per night from 6 Jan to 7 Jan
NZ$252
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3-star beach hotel in Port Antonio. Enjoy a private beach, daily housekeeping, and a garden. Popular attractions Frenchman's Cove Beach and San ...
Frenchman's Cove Resort
Don't see what you're looking for?
See all available properties in Portland
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More ways to explore Portland

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