Book Holiday Homes in Portland

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Featured Holiday Homes in Portland

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$184 per night from 2 Apr to 3 Apr
NZ$184
includes taxes & fees
2 Apr - 3 Apr
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
Very cozy, clean, close to Bob Marley Beach, Cane River Falls & close to airport

Very cozy, clean, close to Bob Marley Beach, Cane River Falls & close to airport

Bull Bay
The price is NZ$136 per night from 2 Apr to 3 Apr
NZ$136
includes taxes & fees
2 Apr - 3 Apr
Stay at this vacation home in Kingston. Enjoy free WiFi, air conditioning, and an indoor pool. Popular attractions Wickie Wackie Beach and Nelson Mandela Park ...
Very cozy, clean, close to Bob Marley Beach, Cane River Falls & close to airport
Cute and Cozy Ez Home

Cute and Cozy Ez Home

Portmore
The price is NZ$220 per night from 15 Apr to 16 Apr
NZ$220
includes taxes & fees
15 Apr - 16 Apr
Stay at this vacation home in Portmore. Enjoy free WiFi, private pools, and a garden. Popular attractions Sovereign Village Mall and Old Gaol House are located ...
Cute and Cozy Ez Home
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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$176 per night from 15 Apr to 16 Apr
NZ$176
includes taxes & fees
15 Apr - 16 Apr
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
El Paraíso @ The Westbury •Cozy 2BR Apt in New Kingston

El Paraíso @ The Westbury •Cozy 2BR Apt in New Kingston

Kingston
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 ...
El Paraíso @ The Westbury •Cozy 2BR Apt in New Kingston
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.
Beautiful Townhouse in Gated Kingstons Haven

Beautiful Townhouse in Gated Kingstons Haven

Kingston
The price is NZ$359 per night from 2 Apr to 3 Apr
NZ$359
includes taxes & fees
2 Apr - 3 Apr
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
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
Stay at this vacation home in Kingston. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Nelson Mandela Park and National Dance Theatre ...
Home Sweet Home. 7 minutes from Kingston Airport, 20 mins to Bob Marley Museum!
Sleepover 3BR Cottage in Kingston

Sleepover 3BR Cottage in Kingston

Kingston
Stay at this vacation home in Kingston. Enjoy air conditioning. Popular attractions Bob Marley Museum and Jamaica House are located nearby.
Sleepover 3BR Cottage in 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
499 Holiday Homes
Lowest Price
NZ$136
Highest Price
NZ$814
Popular accommodation
constructed fully furnished two bed bedroom house with one and half bathroom, Very cozy, clean, close to Bob Marley Beach, Cane River Falls & close to airport, Cute and Cozy Ez Home, Charming 1-bedroom hotel with WiFi and AC in vibrant Kingston, El Paraíso @ The Westbury •Cozy 2BR Apt in New Kingston, Brand new luxury apartment located in New Kingston., Beautiful Townhouse in Gated Kingstons Haven, Home Sweet Home. 7 minutes from Kingston Airport, 20 mins to Bob Marley Museum!, Sleepover 3BR Cottage in Kingston

Top trending hotels in Portland

Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield, Port Antonio, Portland
Fully refundable
The price is NZ$357 per night from 14 Apr to 15 Apr
NZ$357
includes taxes & fees
14 Apr - 15 Apr
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
Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig, Long Bay, Portland
Fully refundableReserve now, pay when you stay
The price is NZ$361 per night from 2 Apr to 3 Apr
NZ$361
includes taxes & fees
2 Apr - 3 Apr
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
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is NZ$814 per night from 22 Apr to 23 Apr
NZ$814
includes taxes & fees
22 Apr - 23 Apr
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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Match Resort Hotel

Match Resort Hotel

3 out of 5
Dolphin Bay, Port Antonio
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 8 Apr to 9 Apr
NZ$192
includes taxes & fees
8 Apr - 9 Apr
Stay at this 3-star hotel in Port Antonio. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions ...
Match Resort Hotel
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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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