Portland Holiday Rentals from NZ$157: Search Short-Term Rentals

A clear turquoise sea, a small island with dense green foliage, and a clear blue sky.

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Top Cities in Portland

A tropical beach with clear blue waters, sandy shore, and lush greenery.

Our top choices for Portland holiday rentals

1. Windbreak Villa

Buff Bay

includes taxes & fees

8 Aug - 9 Aug

2. Private Oasis - Portland’s Coastal Gated Hideaway

Fair Prospect

"The listing didn’t really represent this quant hideaway. I grew up in this community so it was great visiting and have this place to decompress and chill. Very cute spot, the host was super, asked if I needed anything at the store and he was very available to assist as needed, I had my ex to assist so didn’t need him, but he checked if I needed anything and was available if I did. And the view from the gazebo was my favourite. You will not be disappointed perfect for couples or just friends...

Janet

includes taxes & fees

2 Sept - 3 Sept

3. Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

Port Antonio

includes taxes & fees

13 Aug - 14 Aug

1 bedroom, iron/ironing board, free WiFi, bed sheets

4. Views from every angle - 2nd floor cozy villa

Port Antonio

includes taxes & fees

14 Aug - 15 Aug

5. Port Antonio East Side Villa

Port Antonio

includes taxes & fees

8 Aug - 9 Aug

6. Bright Country Apartment at Robin Hood guesthouse

Port Antonio

includes taxes & fees

8 Aug - 9 Aug

7. Downstairs Bedroom at Robin Hood guesthouse

Port Antonio

includes taxes & fees

8 Aug - 9 Aug

8. Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland

Port Antonio

includes taxes & fees

9 Aug - 10 Aug

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Top Portland Hotel Reviews

R Hotel Kingston

8/10 Good

"Clean rooms, good place to stay, quiet, great staff. But late breakfast"

Jamaica Palace Hotel

8/10 Good

"The property is well maintained. The staff were excellent. Breakfast was great every morning. We opted for the Jamaican breakfast and they didn’t disappoint. The rooms and bathrooms were clean, however one area that could be improved is the bathroom accessibility. The bathrooms were not equipped to adequately accommodate guests with limited mobility. Features such as accessible showers, grab bars, and sufficient space for maneuverability were lacking, which could make the stay challenging for guests with mobility needs. Improving these accommodations would make the hotel more inclusive and comfortable for all visitors. One other drawback was the unavailability of coffee and tea options in the rooms or even the common area. This is something they should consider improving. We also loved the pool area. The Jamaican Map design was a great idea. There were lots of lounge chairs, tables and umbrellas. Overall my family and I had a great time. I would stay here again."

Match Resort Hotel

8/10 Good

"This is a charming little resort. The staff, especially Mackenzie and Jodie, were very personable and friendly at all times. The rooms were adequate and fairly spacious, with comfortable beds, smart TVs as advertised, and functional minifridges. Despite a limited variety, the breakfast was adequate. One clear area for improvement, however, is property maintenance. There seems to be a plumbing issue which resulted in partially clogged drains and leaky ceilings. The pool was uninviting, and some of the amenities, like the bar and restaurant, were unmanned (though you could still place an order at the front desk). If you're looking for an affordable place to rest comfortably while you check out the attractions in Portland, this could be the place for you!"

Great Huts

10/10 Excellent

"More Than a Hotel—A True Jamaican Experience Great Huts is not just a hotel—it is an experience. The property stretches from the cliffs down to the beach, with winding paths through sea grape trees, coral rock, African-inspired art, treehouses, hidden sitting areas, and incredible views of the Caribbean. Everywhere you look feels like a postcard. We stayed in a treehouse and absolutely loved it. The room was unique, peaceful, and surrounded by nature. At night, the property became even more magical with warm lighting, ocean sounds, and a relaxed atmosphere. The staff was one of the best parts of our stay. Everyone was kind, attentive, welcoming, and genuinely cared about making sure we were comfortable. The food was also delicious, especially breakfast, and the dining area has so much character. Great Huts also helped arrange transportation and local experiences, including our Rio Grande rafting trip. They connected us with trusted people who took excellent care of us from beginning to end. This is not a typical polished resort with identical rooms and concrete hallways. It is rustic, artistic, cultural, and built into the natural landscape. That is exactly what makes it special. We had a tremendous stay and would absolutely return. Great Huts became one of the highlights of our entire Jamaica trip."

Moon San Villa at the Blue Lagoon

8/10 Good

"The property is perfectly located next to blue lagoon and the resort is beautiful. It could use some maintenance was a bit dusty, needed some refurbishing. There wasn’t any toiletries as the bookings saiid or the free boat ride so that should be updated. It is hard to get in contact with someone on site when needed. There is someone that pops in from time to time but no number to call. That would be nice to have. TVs don’t connect to wifi or have channels either. All in all it was a nice spot a/c works great, bed is comfy, the view is great, very welcoming and private. I would definitely go back"

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as NZ$157 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Room 1

Change your mind

Treat yourself

Be picky

Top Cities in Portland

Long Bay

Our top choices for Portland holiday rentals

1. Windbreak Villa

2. Private Oasis - Portland’s Coastal Gated Hideaway

3. Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

4. Views from every angle - 2nd floor cozy villa

5. Port Antonio East Side Villa

6. Bright Country Apartment at Robin Hood guesthouse

7. Downstairs Bedroom at Robin Hood guesthouse

8. Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland

9. DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

10. Horse Shoe Villas A family friendly 2 bedroom villa near to it all

11. Horse Shoe Villa Port Antonio air conditioned close to it all family friendly

12. Ahh! (Pool/Ocean View Room w/ Private Bath)

13. Jamaica House - The Blue Mountain Wilderness Retreat

14. Pearl Ocean Villa

15. Teejay's rustic retreat

16. Ridge Bay Chateau

17. Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure

18. Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland

19. Rockery Villa Cozy Hideaway for Couples. Come Relax and Enjoy cool sea breezes.

20. One Bedroom Sea View Villa, Frenchman's Cove Resort

Find holiday rentals that suit your style

Top Portland Hotel Reviews

R Hotel Kingston

S Hotel Kingston

AC Hotel by Marriott Kingston, Jamaica

ROK Hotel Kingston, Tapestry Collection by Hilton

Jamaica Palace Hotel

Match Resort Hotel

Sea Cliff Resort

Great Huts

Moon San Villa at the Blue Lagoon

Find out more about Portland