Portland Holiday House Rentals from AU$132: Search Holiday Homes

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 beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.

Our top choices for Portland holiday homes

A coastal view with clear turquoise waters and a grassy foreground.

1. Ac'ed 2 bedroom Beach House

Hellshire

Chevaughn G.

includes taxes & fees

19 Oct - 20 Oct

A living room with a sofa, a glass coffee table, and red patterned curtains.

2. Charming 2-bedroom house in Portmore with WiFi, AC

Portmore

Sophia

includes taxes & fees

17 Oct - 18 Oct

A swimming pool area with a waterfall feature, a television screen, and a mural of a house.

3. Cute and Cozy Ez Home

Bridgeport

shardae w.

includes taxes & fees

17 Oct - 18 Oct

A modern building with two large garage doors, a tiled roof, and a well-maintained lawn.

4. 1Bdrm, A/C, Wi-Fi, Washer & Dryer - Spacious Apt

Barbican

Fouh E.

A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

5. Phoenix Park Villas Portmore

Portmore

Kimoya

includes taxes & fees

17 Oct - 18 Oct

A view of a coastal area with lush greenery, a small building, and a body of water.

6. Perfect View - Entire House

Drapers

"I loved the one bedroom apartment located downstairs with a large bedroom that had a comfortable and clean king size bed. I loved the air conditioning through out the apartment. Beautiful large windows to let sun in if desired or keep it close and use light throughout. Well lit inside and out. Easy code access, no physical keys to loose. Wash & dryer room. Powerful shower. Complete kitchen with open dining to seat 4 or more. Excellent choice in color scheme for decor. Really lovely and peaceful...

Andrea

A large, multi-story building with a swimming pool and outdoor seating area.

7. The Palms at Galina Luxury Rental Fully Staffed

Galina

Letesa K.

A covered outdoor seating area with blue chairs and a metal table.

8. FULLY APPOINTED HOME AWAY FROM HOME

Harbour View

Winsome T.

includes taxes & fees

17 Oct - 18 Oct

A clear blue pool surrounded by a white fence, palm trees, and a cloudy sky.

9. Taylormade Golf Retreat III

Kingston

Arlana

A modern living room with a grey sofa, a potted plant, and a colorful rug.

10. Charming 2-bedroom property, in Exclusive gated community

Caribbean Estates

Cleata B.

A modern kitchen with dark cabinets, a central island, a microwave, a toaster, and a sink.

11. La Petite Maison

Greater Portmore

Salom

A bedroom with a bed, a dresser, a mirror, and two windows with curtains.

12. Pond View 1BR Apartment • Peaceful Pamphret Stay

Pamphret

A brightly colored room with orange and blue walls, wicker furniture, and a glass coffee table.

13. ★ Cozy Kingston Getaway ★ Relaxing, Quaint & Centrally Located ★

Ziadie Gardens

Claudette N.

A balcony with a view of the sea, a yellow building, and a table with chairs.

14. 2-bedroom modern oceanview home in Port Antonio, 15 mins from beaches

Port Antonio

A spacious living area with a white sectional sofa, a round coffee table, and a view of the outdoors through large windows.

15. Amazing Caribbean Sea & Mountain Views, Luxury, Privacy, 4 bd suites, sleeps 12

San San

"This is a property built in the 70s that have not been upgraded since the 90s other than the clim units in the bedrooms. The main living area of the house is open do not have clim. During dinner, we were sweating a lot and we ended up with multiple bugs bites. The house has no real windows, it’s only ventilation shutters that separate you from outside. On the positive side, we ate extremely well and the staff was great. So pictures of the house on the website are deceiving and were probably...

Anonymous traveller

16. The Golf Oasis II

Kingston

A living room with two blue sofas, a black coffee table, and a vase with yellow flowers.

17. Charming 3-bedroom house in wonderful Kingston with WiFi, AC.

Kingston

A beach with pebbles, waves, and dense green foliage.

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

Port Antonio

Troy W.

A bedroom with a wooden bed, two bedside tables with lamps, an air conditioner, and a window with curtains.

19. 2 Bedroom Townhouse at Surbiton Square

Half Way Tree

"I've never given any property a full 5 out of 5, but this place is worth it and more. The property looks exactly as nice as the pictures, Beautiful and spacious, the area is secured and in a perfect location, can get to Brooklyn Grocery Store or Mega Mart with ease, the Manager was easy to get in touch with and responded quickly. I've always stayed in hotels and/or Family members houses but as long as this is available I'll not stay any where else when i return to Kingston. The ease of cooking...

Tamiko

A balcony with a wooden bench, white balustrades, and a tiled floor.

20. Spacious Port Antonio villa w/360° Sea & Mountain Views

Port Antonio

Dale M.

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Top Portland Hotel Reviews

Great Huts

10/10 Excellent

"Great Huts is an amazing African cultural experience with great art in a natural setting. We stayed in a two-story tree house with a view of Boston Bay. The staff is friendly and very helpful. The food and entertainment are amazing. I highly recommend staying at the Great Huts at least once."