Portland holiday rentals

We found 1,441 holiday rentals — enter your dates for availability
Discover a selection of 89 homes, 163 apartments and other holiday rentals in Portland that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, including parking and a TV. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Portland

Showing deals for:27 Nov - 4 Dec

2nd Floor: Dining area looks out over the marsh side.
2nd Floor: Spiral stairs lead to ocean view attic bunk room.
2nd Floor: bistro with sliders to the deck and large yard below.
2nd floor: Living area with electric fireplace. Smart TV upgraded to 60” in 2023
Exceptional
(70 reviews)

Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Scarborough

20% off
S$7,755
for 7 nights, 1 home
S$1,108 per night
includes taxes & fees
Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard
Living room has queen size pull out sofa bed.
Property grounds
Floors recently refinished.
Open floor plan.
Wonderful
(40 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
S$4,929
for 7 nights, 1 home
S$704 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Kitchen
Casco Bay
picnic area
Dining area
Exceptional
(101 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
S$2,755
for 7 nights, 1 apartment
S$394 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
Interior
Interior
Interior
Beach
Exceptional
(23 reviews)

A Commanding View of Town of Old Orchard Beach

Old Orchard Beach

8% off
S$3,764
for 7 nights, 1 home
S$538 per night
includes taxes & fees
A Commanding View of Town of Old Orchard Beach
Interior
Interior
Private kitchen
Terrace/patio
Exceptional
(17 reviews)

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Scarborough

8% off
S$4,455
for 7 nights, 1 home
S$636 per night
includes taxes & fees
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Screened porch off of patio
Lovely Craftsman-style details greet guests at the front door
Open concept main floor with charming original Craftsman woodwork
Huge dining table and pass-through to kitchen
Exceptional
(79 reviews)

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Portland

8% off
S$9,459
for 7 nights, 1 home
S$1,351 per night
includes taxes & fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Living area
Terrace/patio
Room
Private kitchen
Exceptional
(185 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
S$2,010
for 7 nights, 1 apartment
S$287 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Private kitchen
Beach
Room
Interior
Exceptional
(56 reviews)

Cozy 1 BR Condo Steps From The Beach

Old Orchard Beach

8% off
S$1,618
for 7 nights, 1 apartment
S$231 per night
includes taxes & fees
Cozy 1 BR Condo Steps From The Beach
Private kitchen
Room
Property grounds
Dining
Wonderful
(14 reviews)

Updated cottage, walk to beach, screened in porch

Old Orchard Beach

8% off
S$1,998
for 7 nights, 1 home
S$285 per night
includes taxes & fees
Updated cottage, walk to beach, screened in porch
Private kitchen
Living area
Dining
Private kitchen
Exceptional
(134 reviews)

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Portland

11% off
S$2,745
for 7 nights, 1 apartment
S$392 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Dining
Living area
Interior
Room
Exceptional
(40 reviews)

Pine Point Beach private, quaint, charming studio.

Scarborough

8% off
S$1,827
for 7 nights, 1 apartment
S$261 per night
includes taxes & fees
Pine Point Beach private, quaint, charming studio.
Massive 100 inch smart TV
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
View from inside unit.
Exceptional
(7 reviews)

Exchange Street Skylight Loft

Portland

8% off
S$3,669
for 7 nights, 1 apartment
S$524 per night
includes taxes & fees
Exchange Street Skylight Loft
Space for shoes and coats before going upstairs into the living space.
Walk around behind the garage to access the apartment.
Your private deck and entrance.
Room
Exceptional
(12 reviews)

Private studio nestled in woods outside Portland

Westbrook

12% off
S$2,168
for 7 nights, 1 apartment
S$310 per night
includes taxes & fees
Private studio nestled in woods outside Portland
Interior
Tour the Victorian Mansion at the bottom of the street.
Scales! The best spot in town for a delish dinner.
Living area
Exceptional
(60 reviews)

Historic Home in the West End. Private Parking.

Portland

8% off
S$2,300
for 7 nights, 1 apartment
S$329 per night
includes taxes & fees
Historic Home in the West End. Private Parking.
Living area
Marina
Private kitchen
Dining
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

15% off
S$2,405
for 7 nights, 1 apartment
S$344 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Private kitchen
Outdoor dining
Property grounds
Living area
Exceptional
(27 reviews)

Direct ocean views from extra large balcony! Over 1200 square feet!

Old Orchard Beach

8% off
S$2,522
for 7 nights, 1 apartment
S$360 per night
includes taxes & fees
Direct ocean views from extra large balcony! Over 1200 square feet!
Living area
Interior
Exterior detail
Dining
Exceptional
(99 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
S$2,592
for 7 nights, 1 apartment
S$370 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Interior
Dining
Private kitchen
Outdoor dining
Exceptional
(147 reviews)

Fall In Love With Portland!

Portland

7% off
S$2,501
for 7 nights, 1 apartment
S$357 per night
includes taxes & fees
Fall In Love With Portland!
Large deck with seating for six, festive lighting and a firepit. Views and sun!
5 min car ride to Downtown/Old Port.
Large, well-stocked Kitchen w/stainless steel counter and appliances
Festive lighting at your control.
Exceptional
(131 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

6% off
S$2,858
for 7 nights, 1 apartment
S$408 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Living area
Interior
Walnut topped kitchenette counter with coffee maker.
Room
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
S$3,991
for 7 nights, 1 apartment
S$570 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Interior
Interior
Room
Living area
Exceptional
(20 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
S$4,198
for 7 nights, 1 apartment
S$600 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
Living area
Property grounds
Room
Exterior
Exceptional
(155 reviews)

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

Old Orchard Beach

14% off
S$2,092
for 7 nights, 1 apartment
S$299 per night
includes taxes & fees
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Interior
tour the Victoria Mansion at the bottom 
of the street
Scales! The best spot in the Old Port for upscale New England Seafood.
the State Theater is a 5-minute stroll up the street
Exceptional
(58 reviews)

Bright & Sunny West End Apartment with Private Parking.

Portland

8% off
S$3,563
for 7 nights, 1 apartment
S$509 per night
includes taxes & fees
Bright & Sunny West End Apartment with Private Parking.
Discover Victoria Mansion at the bottom of the street.
Scales in the Old Port for the best seafood
Interior
The State Theater is a 5 minute walk away.
Exceptional
(53 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
S$2,473
for 7 nights, 1 apartment
S$353 per night
includes taxes & fees
Charming West End Hideaway. Private Parking
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Delight in the waterfront landscape of Portland

Enjoy the area's live music, museums and theatre scene with a rental holiday home in Portland. This cosmopolitan city attracts visitors thanks to its seafood restaurants and shopping. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Portland

Do you want to discover attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Portland a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Aquaboggan Water Park (10.8 mi / 17.3 km)
  • Dunegrass Golf Club (11.8 mi / 18.9 km)
  • Pirate's Cove (12 mi / 19.3 km)
  • Funtown Splashtown USA (12.7 mi / 20.5 km)
  • Old Orchard Beach Parasail (15.1 mi / 24.2 km)
  • Len Libby Chocolates (7.6 mi / 12.3 km)

Exploring the natural features in Portland

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Portland. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Eastern Promenade (0.8 mi / 1.3 km)
  • East End Beach (0.9 mi / 1.4 km)
  • Willard Beach (1.8 mi / 2.9 km)
  • Thompson's Point (2 mi / 3.2 km)
  • Sand Beach (2.2 mi / 3.5 km)
  • Higgins Beach (7 mi / 11.2 km)

Travelling to and around Portland

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 2.9 mi (4.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 26.8 mi (43.2 km) away.

If you prefer train travel, the main station is Portland Transportation Center.

Frequently asked questions

What is the best area to stay in Portland when booking a holiday rental?
One of the more popular neighbourhoods to experience a holiday home in Portland is Downtown Portland. Base yourself here and you won't be too far from leading visitor attractions like Portland Museum of Art and Wadsworth-Longfellow House.
What is the most popular type of holiday rental accommodation in Portland?
Apartments are the most popular style of holiday rental in Portland, according to our data. Even if you've got a different idea about what you'd like, Vrbo has holiday homes in a variety of shapes and sizes. Compare our options to find your perfect match.
How much does it cost to rent a holiday rental in Portland?
The average price for a holiday rental in Portland is based on several factors, including season, property type and length of stay. Whether you prefer a sprawling villa with room to move around or a quaint cabin for just you and the kids, just enter your travel dates to discover some great-value stays.
How much does it cost to rent a beach house in Portland?
The average price for a holiday home by the beach in Portland will depend on when you're going and the style and size of property you're looking for. You can easily and quickly find prices on Vrbo by entering the dates you'll be travelling. Then use our filters to pick the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Portland?
Yes, there are. Take your pick of 189 holiday rentals that allow pets in Portland on Vrbo. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly holiday rentals to find a pad where your pup can get in on the fun.
Can I rent a house with a pool in Portland?
Mark the "pool" box in our handy filter tool and select from 17 houses with private pools in Portland on Vrbo. Morning soak, afternoon splash or midnight swim? How you spend your free time is up to you when your holiday home has a swimming pool.
What are popular rental amenities in Portland?
When it comes to rental amenities that people are searching for in Portland, mountain views, an electric car charging station and a garden rank highest. With Vrbo holiday homes, there are choices to match your taste and style, whether you're travelling with your partner, your family or even pets.
Are there large group holiday rentals in Portland?
Portland has 17 holiday properties that can accommodate 10 or more people. These stays come with all the space you need to share good times with your favourite people.
Are there holiday rentals in Portland that welcome kids?
Portland has 185 family-friendly holiday homes. And securing a stay that welcomes kiddos is a breeze with Vrbo's "Properties good for families" filter. As well as having the whole place to yourselves, you'll get access to conveniences and perks like bunk beds, kitchens and private pools.
What are the top attractions for families in Portland?
There are tons of exciting things to see and do with the family in Portland, including:
  • Higgins Beach
  • East End Beach
  • Pine Point Beach
Are there one-bedroom holiday rentals in Portland?
You can choose from 65 one-bedroom rentals in Portland. Whether you'd prefer a townhouse or a condo, our one-bedroom properties are perfect if you don't require a lot of space. One of the main perks of having your own digs? You'll never need to share your getaway with strangers.
Can I find two-bedroom holiday rentals in Portland?
Take off with your loved ones and experience complete comfort and privacy in one of the 57 two-bedroom holiday rentals Portland has to offer.
Are there holiday rentals with WiFi in Portland?
Portland has 95 holiday rentals with WiFi, so you can stay connected while you're on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to sending emails, these Vrbo homes make it a breeze to get online.
How can I find holiday rentals with air conditioning in Portland?
You can pick from 161 holiday homes with air conditioning in Portland giving you that gentle, cool breeze and extra level of comfort. Simply enter your desired travel dates and then use our handy filter tool to help you book properties with air conditioning.
How old do you have to be to rent a holiday rental in Portland?
It's a good idea to check with the Portland holiday rental you want on Vrbo as the age limit varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday rental in Portland for?
The amount of time you can book a Portland holiday home for differs depending on the property. Simply tap in your preferred travel dates to see available options offering longer term stays. They include all you require to make your extended holiday more enjoyable and convenient, like laundries and air conditioning. Some Vrbo holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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