Portland holiday rentals

We found 1,402 holiday rentals — enter your dates for availability
Discover a selection of 90 homes, 165 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:11 Dec - 18 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
(72 reviews)

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

Scarborough

20% off
AU$8,099
for 7 nights, 1 home
AU$1,157 per night
includes taxes & fees
Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard
Bathroom
Bright and comfortable living room in a quiet Portland neighborhood
Fully equipped kitchen with everything needed for cooking
Room
Exceptional
(50 reviews)

Quiet 2BR/2BA Home w/ Parking • Dog-Friendly • Near Downtown Portland

Portland

8% off
AU$3,228
for 7 nights, 1 home
AU$461 per night
includes taxes & fees
Quiet 2BR/2BA Home w/ Parking • Dog-Friendly • Near Downtown Portland
Exterior
Living area
Interior
Private kitchen
Exceptional
(21 reviews)

Entire House - three suites - conferences, reunions, retreats

Westbrook

8% off
AU$9,868
for 7 nights, 1 home
AU$1,410 per night
includes taxes & fees
Entire House - three suites - conferences, reunions, retreats
Kitchen recently renovated.
Property grounds
Living room has queen size pull out sofa bed.
Open floor plan.
Wonderful
(40 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
AU$5,154
for 7 nights, 1 home
AU$736 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Exterior
Private kitchen
Outdoor dining
Private sandy beach area
Wonderful
(5 reviews)

Lakefront 15 mins from Portland with Private Beach and Fenced in Yard

Windham

20% off
AU$7,085
for 7 nights, 1 home
AU$1,012 per night
includes taxes & fees
Lakefront 15 mins from Portland with Private Beach and Fenced in Yard
Master bedroom with queen bed and ceiling fan
Willard Beach
Back yard
Dining
Exceptional
(72 reviews)

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

South Portland

8% off
AU$4,415
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Kitchen
Casco Bay
Dining area
WELCOME
Exceptional
(101 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
AU$2,920
for 7 nights, 1 apartment
AU$417 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
The living room leads out to a private deck with a dining table that seats 4.
Outdoor dining
Private kitchen
Exterior detail
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
AU$3,950
for 7 nights, 1 home
AU$564 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
Interior
Interior
Terrace/patio
Private kitchen
Exceptional
(17 reviews)

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

Scarborough

8% off
AU$4,369
for 7 nights, 1 home
AU$624 per night
includes taxes & fees
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Kitchen at night with setup for a dinner party
Looking up to the house from Garrison Cove
View from Roof Top deck
Dining Room Seating for ten, extra dining also available
Exceptional
(86 reviews)

Amazing Views, and Comfortable Spaces in this Well Appointed Island Home

Bailey Island

8% off
AU$8,364
for 7 nights, 1 home
AU$1,195 per night
includes taxes & fees
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Private kitchen
Interior
Interior
Beach
Exceptional
(23 reviews)

A Commanding View of Town of Old Orchard Beach

Old Orchard Beach

8% off
AU$3,945
for 7 nights, 1 home
AU$564 per night
includes taxes & fees
A Commanding View of Town of Old Orchard Beach
Living area
Terrace/patio
View from living room
Room
Exceptional
(189 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
AU$2,143
for 7 nights, 1 apartment
AU$306 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Exterior
Beach
Interior
Room
Exceptional
(58 reviews)

Cozy 1 BR Condo Steps From The Beach

Old Orchard Beach

8% off
AU$1,715
for 7 nights, 1 apartment
AU$245 per night
includes taxes & fees
Cozy 1 BR Condo Steps From The Beach
Living area
Marina
Private kitchen
Dining
Exceptional
(13 reviews)

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

South Portland

16% off
AU$2,547
for 7 nights, 1 apartment
AU$364 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Open concept main floor with charming original Craftsman woodwork
Lovely Craftsman-style details greet guests at the front door
Warm and inviting living room with gas fireplace
Huge dining table and pass-through to kitchen
Exceptional
(80 reviews)

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

Portland

8% off
AU$9,421
for 7 nights, 1 home
AU$1,346 per night
includes taxes & fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Large open concept living space with tall sloped celling and a loft.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Exceptional
(7 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,924
for 7 nights, 1 apartment
AU$561 per night
includes taxes & fees
Exchange Street Skylight Loft
Living area
Private kitchen
Dining
Interior
Exceptional
(49 reviews)

Large three bedroom condo, steps from beach and amusement area

Old Orchard Beach

8% off
AU$5,216
for 7 nights, 1 apartment
AU$745 per night
includes taxes & fees
Large three bedroom condo, steps from beach and amusement area
Dining
Living area
Private kitchen
Interior
Exceptional
(41 reviews)

Pine Point Beach private, quaint, charming studio.

Scarborough

8% off
AU$1,892
for 7 nights, 1 apartment
AU$270 per night
includes taxes & fees
Pine Point Beach private, quaint, charming studio.
Your private deck and entrance.
Walk around behind the garage to access the apartment.
Space for shoes and coats before going upstairs into the living space.
Private kitchen
Exceptional
(14 reviews)

Private studio nestled in woods outside Portland

Westbrook

13% off
AU$2,141
for 7 nights, 1 apartment
AU$306 per night
includes taxes & fees
Private studio nestled in woods outside Portland
Interior
Outdoor dining
Private kitchen
Dining
Exceptional
(13 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,169
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Dining
Room
Property grounds
Private kitchen
Wonderful
(14 reviews)

Updated cottage, walk to beach, screened in porch

Old Orchard Beach

8% off
AU$2,280
for 7 nights, 1 home
AU$326 per night
includes taxes & fees
Updated cottage, walk to beach, screened in porch
Off-street parking behind building dedicated to this unit only.
Living area
Room
Interior
Exceptional
(40 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$2,682
for 7 nights, 1 apartment
AU$383 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Private kitchen
Dining
Interior
Living area
Exceptional
(147 reviews)

Fall In Love With Portland!

Portland

7% off
AU$2,708
for 7 nights, 1 apartment
AU$387 per night
includes taxes & fees
Fall In Love With Portland!
Living area
Interior
Dining
Exterior detail
Exceptional
(99 reviews)

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

Portland

8% off
AU$2,834
for 7 nights, 1 apartment
AU$405 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
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  • All the privacy of home

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

    More space, more privacy, more amenities — more value

Why visit Portland

  • Stunning coastal scenery: Explore breathtaking beaches and picturesque waterfront views that showcase the natural beauty of Maine.
  • Historic charm: Discover well-preserved historic houses and landmarks that reflect Portland's rich cultural heritage.
  • Outdoor activities: Enjoy various outdoor pursuits, from hiking in nearby parks to leisurely strolls along the scenic coastline.
  • Vibrant local culture: Experience the bustling downtown area filled with eclectic shops, eateries, and lively cultural events.
  • Iconic lighthouses: Visit Portland's famous lighthouses, iconic symbols of the city's maritime history.

Popular types of accommodation in Portland

Discover Portland, Maine – a charming coastal city offering seaside stays and cosy holiday rentals. Enjoy a selection of private holiday homes, quaint cottages, and stylish condos, each promising a quintessential Maine experience. From scenic waterfront views to vibrant local culture, your stay in this historic city is sure to be both refreshing and memorable.

  • Private Holiday Homes: These are standalone residences offering privacy and exclusivity, making them the top choice for visitors seeking a unique holiday retreat in Portland.
  • Cottages: Quaint and charming, cottages provide a cosy escape, ideal for those desiring a picturesque stay in the city.
  • Condos: Modern and convenient, condos offer a blend of style and comfort for holidaymakers exploring Portland.
  • Apartments: Well-appointed apartments deliver practicality and ease, perfect for a comfortable urban experience.
  • Cabins: Rustic and intimate, cabins offer a distinctive getaway for travellers looking for a more laid-back escape.**

Top attractions in Portland

Portland, Maine, is a charming city perfect for outdoor enthusiasts and families alike. Visitors can enjoy stunning beaches, explore historic houses, and admire iconic lighthouses. The city offers a rich cultural experience alongside beautiful scenery, making it an ideal destination for those seeking adventure or relaxation. With its blend of history and nature, Portland promises memorable experiences for every traveller.

  • Sand Beach: Experience the tranquil beauty of Sand Beach, where soft sands meet gentle waves, perfect for sunbathing and beach activities. Enjoy picturesque views and a relaxed atmosphere, ideal for unwinding amidst nature.
  • Victoria Mansion: Step back in time at Victoria Mansion, a stunning example of Italianate architecture. This historic house museum offers a glimpse into 19th-century opulence, showcasing exquisite furnishings and rich cultural history.
  • International Cryptozoology Museum: Delve into the world of the unknown at the International Cryptozoology Museum, where you can explore fascinating exhibits on mythical creatures and legendary beasts, blending curiosity and culture in a unique setting.

Things to do recommended for couples

Seeking a romantic escape in Portland? Explore the charming Old Port district with its cobblestone streets, indulge in a sunset cruise along Casco Bay, or share a candlelit dinner at a waterfront restaurant, savouring fresh seafood and stunning views. Perfect for couples looking to connect.

Things to do recommended for families

Families will love exploring the Children's Museum & Theatre of Maine, where interactive exhibits spark creativity. A visit to the Portland Head Light offers stunning coastal views, while the scenic ferry ride to Peaks Island provides a delightful day out with beaches and bike rentals for all ages.

Things to do recommended for groups

Experience the thrill of racing at Beech Ridge Motor Speedway, located 11km from Portland. Perfect for groups, this venue offers an exhilarating atmosphere filled with sports and adventure vibes, ensuring an unforgettable outing for everyone in your party.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Portland

Regardless of whether you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to refine your search according to your key priorities. Here are some helpful booking tips for Stayz.

  • Traveling to Portland with a group: Think about how many bedrooms you require, along with amenities like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and more on Stayz.
  • Traveling to Portland with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Portland: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, explore Stayz properties that welcome pets. The majority of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities such as a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Best time to go to Portland

If you're planning a trip to Portland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January26.1°F (-3.3°C)Light RainMostly SunnyLowSlightly Low
February27.0°F (-2.8°C)Light RainMostly SunnyLowSlightly Low
March33.4°F (0.8°C)Light RainMostly SunnyLowSlightly Low
April43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
May54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
June61.9°F (16.6°C)Light RainMostly SunnyHighSlightly High
July68.9°F (20.5°C)Light RainMostly SunnyHighSlightly High
August68.5°F (20.3°C)Light RainMostly SunnyHighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly SunnyAverageAverage

Booking with Stayz is a breeze

Are you eager to save on your upcoming journey? Being flexible with your travel dates can lead to considerable savings, as prices often fluctuate. Additionally, booking an extended stay can unlock even greater discounts. To discover a Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a dedicated area to initiate new journeys, continue your plans, or review and arrange your bookings. Properties you have either saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • Dunegrass Golf Club (11.8 mi / 18.9 km)
  • Seacoast Adventure (16.4 mi / 26.5 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.