A coastal town with colorful houses, a prominent hill in the background, and a clear blue sky.

Portland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Portland vacation rentals

A kitchen with a dining table, chairs, a window with curtains, a potted plant, and a pot on the counter.

1. Lighthouse View

Lighthouse View
3.5 star property
Portland
6.0 out of 10, (1 review)
"Bed was not comfy as we had backache after second night , we turned mattress round was ok that night but the after that . The step into the shower was too high and we had to buy a step to get in it and also the floor surface was very slippy . Was ck an and tidy and overall not a bad place to stay and would recommend and return at some point "
United Kingdom
Anonymous traveler
The price is P20,041
P24,049 total
includes taxes & fees
Sep 1 - Sep 2
Lighthouse View
A spacious kitchen with a dining area, a grey sofa, and a vintage trunk.

2. Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"Very nice cottage in quiet location with room opening onto garden with lots of bird song. Snug with TV is very comfortable. Parking spot just outside cottage. Well appointed kitchen. Location is good for access to portland, but going elsewhere requires travelling through Weymouth which can be slow."
United Kingdom
Terry
The price is P34,999
P41,999 total
includes taxes & fees
Sep 3 - Sep 4
Mermaid Cottage
A spacious loft with high ceilings, exposed beams, and large windows. It features a yellow sofa, a blue sofa, and a dining area with a kitchen in the background.

3. Groves House

Groves House
3.0 star property
Portland
The price is P33,210
P39,852 total
includes taxes & fees
Sep 1 - Sep 2
Groves House
A coastal residential area with houses, a grassy field, and a beach with colorful kayaks.

4. Home From Home

Home From Home
3.0 star property
Portland
The price is P33,496
P40,196 total
includes taxes & fees
Aug 26 - Aug 27
Home From Home
A coastal hotel with a paved walkway and seating area, overlooking a pebble beach and cliffs.

5. Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is P34,069
P40,883 total
includes taxes & fees
Sep 13 - Sep 14
Anchor Cottage
A wide, pebbled beach with a clear sky and calm sea.

6. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is P33,067
P39,680 total
includes taxes & fees
Sep 18 - Sep 19
74 Reap Lane
A balcony with a view of a marina and cityscape.

7. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is P43,445
P52,134 total
includes taxes & fees
Sep 12 - Sep 13
Manhattan Beach
A bedroom with a bed, two pillows, a nightstand, a wall-mounted painting, and a window with curtains.

8. Portland View

Portland View
2.0 star property
Portland
The price is P32,351
P38,821 total
includes taxes & fees
Sep 13 - Sep 14
Portland View
A wooden sign with maritime-themed decorations and text, mounted on a green building.

9. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is P50,316
P60,379 total
includes taxes & fees
Sep 2 - Sep 3
Pebbles Reach
A balcony with wicker furniture, a glass table, and a view of the sea and buildings.

10. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is P40,153
P48,183 total
includes taxes & fees
Sep 18 - Sep 19
Bear's Apartment
A pebble beach with a clear sky and calm sea.

11. The Shambles

The Shambles
3.5 star property
Portland
The price is P44,375
P53,251 total
includes taxes & fees
Sep 13 - Sep 14
The Shambles
A dining area with a table set for two, a sofa, and a view of the sea through large windows.

12. Coastguard View

Coastguard View
3.0 star property
Portland
The price is P40,940
P49,128 total
includes taxes & fees
Aug 30 - Aug 31
Coastguard View
A wide, pebbled beach with a clear sky and calm sea.

13. The View

The View
2.0 star property
Portland
The price is P56,328
P67,594 total
includes taxes & fees
Sep 12 - Sep 13
The View
A boat on a pebbled beach with a clear view of the sea.

14. St Johns View

St Johns View
3.5 star property
Portland
The price is P71,502
P85,802 total
includes taxes & fees
Aug 29 - Aug 30
St Johns View
A wide, pebbled beach with a clear sky and calm sea.

15. Sea Gem

Sea Gem
3.5 star property
Portland
The price is P67,851
P81,422 total
includes taxes & fees
Aug 29 - Aug 30
Sea Gem
A dining area with a wooden table and chairs, a kitchen in the background, and a sliding glass door leading to a backyard.

16. Jurassic Coast House

Jurassic Coast House
3.5 star property
Portland
8.0 out of 10, Very Good, (1 review)
"Nice size property. Missing the more luxury/comfort items. Garden furniture ok not as images. Has a comfy dining table. Balcony furniture present but not suitable for the area. High stools and table not appropriate needs more relaxing items to make area useful otherwise it was good for drying clothes. Area is central and easy for amenities, cafes, beach, shops etc all easy to walk to. Noisy as near heliport and some days this is busy from early morning till after 10 at night. Not overly...
United Kingdom
Michelle
The price is P72,361
P86,833 total
includes taxes & fees
Sep 18 - Sep 19
Jurassic Coast House
A rocky beach with waves crashing onto the shore.

17. Kimberlin

Kimberlin
3.5 star property
Portland
The price is P136,991
P164,389 total
includes taxes & fees
Sep 4 - Sep 5
Kimberlin
A spacious loft with high ceilings, exposed wooden beams, and large windows.

18. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is P86,532
P103,839 total
includes taxes & fees
Aug 29 - Aug 30
The Old Portland Courthouse

19. Chandlers Nook

Chandlers Nook
2.0 star property
Portland
The price is P27,341
P32,809 total
includes taxes & fees
Sep 5 - Sep 6
Chandlers Nook
A modern kitchen with a dining area, featuring a large window, a microwave, and a sink.

20. Coastguard Lookout

Coastguard Lookout
2.0 star property
Weymouth
The price is P32,065
P38,478 total
includes taxes & fees
Sep 7 - Sep 8
Coastguard Lookout
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.
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Top Portland Hotel Reviews

Aaran Guesthouse

Aaran Guesthouse

10/10 Excellent
"There was nothing to dislike . The owner could not have been more helpful. She provided us with fresh milk and water every day to keep in a mini fridge ."
Marion 7-night trip
Posted 7 hours ago
Aaran Guesthouse

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Portland!

Frequently asked questions

Can I find a vacation rental in Portland?

Yes, you can find vacation rentals in Portland close to Osprey Leisure Centre, or you can select a more secluded option if you'd like a relaxing place to stay. Tourists appreciate the top-notch restaurants and bars in Portland. Make sure you have time to check out the university setting while you're in the area.

How many vacation rentals will I find in Portland?

Choose from 19 Expedia vacation rentals in Portland for a memorable vacation.

What can I see and do in Portland?

Cultural attractions include Portland Museum and Tout Quarry Sculpture Park, whereas Weymouth Bay and Dorset and East Devon Coast are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Portland Harbour and Portland Bill Lighthouse.

What are vacation rentals like in Portland?

Vacation rentals are private properties you can stay in for a couple days or more in Portland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.