Best Holiday rentals and Airbnb offers in Portland, ME
10 2 reviews
Portland, ME
11/07 – 12/07
£493/nightfor 1 night
Coastal Retreat Steps To The Willard Beach
1 2
apartment , South Portland
This one-bedroom waterfront flat is located in South Portland, a short walk from Willard Beach and offering bay views, with easy access to local cafés and downtown Portland. This apartment sleeps two guests and features off-street parking, an in-unit washer and dryer, a Smart TV with cable, and a heat pump for efficient heating and cooling, making it ideal for a relaxing beach holiday.
9.9 117 reviews
Portland, ME
09/10 – 12/10
£337/nighttotal: £1011 (3 )
Portland Island View 2br Apt.
Views Of Casco Bay
2 3
apartment , Portland
This apartment is situated in a friendly neighbourhood on Casco Bay, just a short drive from the Old Port and its attractions. The property has excellent user, location, and cleanliness ratings, making it a popular choice for visitors. The apartment offers two bedrooms, sleeping up to four guests, and provides a comfortable and well-equipped living space. Guests can enjoy stunning water views, relax on the deck, or make use of the amenities including a fully equipped kitchen, laundry facilities, and a private parking space.
9.9 546 reviews
Portland, ME
17/11 – 19/11
£150/nighttotal: £300 (2 )
Retro Bnb In The Heart Of East End Portland
1 2
apartment , Portland
This Portland, Maine apartment, situated in the East End, is a short walk from East End Beach and numerous restaurants and cafes. The first-floor flat offers keyless entry, a queen-sized bed, a well-equipped kitchen with stainless steel appliances, in-room entertainment including Netflix, Amazon Prime and Hulu, and free on-street parking for up to two guests.
9.9 54 reviews
Portland, ME
30/07 – 02/08
£778/nighttotal: £2334 (3 )
Old Port Loft - 301
1 3
apartment , Portland
This Old Port flat is ideally situated in Portland, Maine, a short walk from the city's waterfront and its many attractions. The two-bedroom, two-bathroom apartment sleeps four guests and boasts a fully equipped kitchen, including a dishwasher, plus ocean views from the third floor.
10 150 reviews
Portland, ME
17/09 – 25/09
£285/nighttotal: £2280 (8 )
Urban Seaside Retreat- East End
Overlook Casco Bay
1 2
apartment , Portland
This Portland apartment, a unique two-level former carriage house on the Eastern Promenade, offers stunning Casco Bay views and is within walking distance of Portland's city centre. The one-bedroom, one-bathroom flat sleeps two, features a fully equipped kitchen, on-street parking, and laundry facilities (for longer stays), and boasts a sunny porch overlooking flower gardens.
9.5 705 reviews
Portland, ME
15/07 – 16/07
£231/nightfor 1 night
2nd Floor, 2 Bedroom , 2 Block Walk To Downtown.
1 3
apartment , Portland
This two-bedroom flat is situated on a quiet side street in Portland’s downtown/Old Port area, just a short walk from the city’s main attractions and a kilometre from the waterfront. The property has consistently received excellent ratings for cleanliness, location, and overall experience. The flat is spacious, with 111 square metres of living space, comfortably accommodating up to four guests. It features a fully equipped kitchen, air conditioning, parking, and a comprehensive guidebook with local information, ensuring a comfortable and enjoyable stay.
9.4 101 reviews
Portland, ME
09/10 – 12/10
£272/nighttotal: £816 (3 )
Back Cove Views
2 3
apartment , Portland
This Portland Back Cove apartment offers a tranquil setting near East End Beach, approximately 5km from Portland International Jetport and within a reasonable driving distance of the Portland Museum of Art and Wadsworth-Longfellow House. The 900-square-metre (approx. 9700 sq ft) property boasts a spacious two-bedroom layout, sleeping up to four guests, and features a fully equipped kitchen, free Wi-Fi, and a flat-screen TV with streaming services.
10 8 reviews
Portland, ME
06/10 – 09/10
£226/nighttotal: £678 (3 )
Howard’s Guesthouse
3 4
apartment , Portland
This three-bedroom flat in Portland offers a prime hilltop position with panoramic views, just a short walk from the Eastern Promenade and East End beach. This two-storey residence accommodates up to five guests, featuring two primary bedrooms with Queen beds, a third bedroom with a Twin daybed and desk, two bathrooms (one with a washer/dryer), a private deck with a grill, and dedicated driveway parking for small to midsize vehicles.
10 75 reviews
Portland, ME
27/07 – 30/07
£564/nighttotal: £1692 (3 )
2 Floor 4 Bed/2 Bath Unit Sthr0037112021
4 9
apartment , Portland
This apartment is situated in a stylish neighbourhood just a short walk from Portland's lively city centre and a few blocks from the waterfront, offering easy access to shops, restaurants, and cultural attractions. It has received excellent ratings for cleanliness, location, and overall user experience. The apartment is a spacious four-bedroom property with two bathrooms, comfortably accommodating up to 12 guests. It features a well-equipped kitchen, a garden, high-speed Wi-Fi, and air conditioning, making it perfect for group trips and comfortable stays.
10 158 reviews
Portland, ME
18/07 – 20/07
£404/nighttotal: £808 (2 )
5 Star Back Cove Apartment With Water View!
1 2
apartment , Portland
This charming house is located in Back Cove, a tranquil neighbourhood just 1.5 kilometres from Casco Bay and the University of Southern Maine. With excellent user ratings, this property is a popular choice for travellers seeking a comfortable and convenient stay in Portland. The house offers one bedroom and one bathroom, with a total floor area of 65 square metres. Guests can enjoy a fully equipped kitchen, a private patio, a garden, and free Wi-Fi, making this a perfect base for exploring all that Portland has to offer.
10 50 reviews
Portland, ME
09/10 – 12/10
£345/nighttotal: £1035 (3 )
Near Portland Trails: Walkable Apartment W/ Deck
1 3
apartment , Portland
This two-bedroom Portland apartment, situated in the Back Cove neighbourhood, offers easy walking access to Portland Trails and is close to the Westbrook College Historic District and Cathedral of the Immaculate Conception. The 93 square metre (1000 square feet) property features a private deck, travel crib, and accommodates up to four guests, with nearby attractions including the Southworth Planetarium and Bayside Bowl.
Portland, ME
14/08 – 16/08
£376/nighttotal: £752 (2 )
Stay Aboard Enchanted – Your Dockside Getaway
1 3
boat , Portland
This dockside accommodation, named Enchanted, offers a unique maritime experience near Portland's cultural and entertainment districts, within 500 meters of its vibrant attractions. Enchanted provides two bedrooms, one bathroom, internet, air conditioning, and a kitchen for up to three guests, with the option for a bay cruise with a captain for an additional fee.
Best family friendly Portland, ME holiday rentals
Among the 959 accommodations in Portland, ME, here are the 4 best family friendly rentals
10 3 reviews
Portland, ME
22/08 – 05/09
£654/nighttotal: £9156 (14 )
Seas The Day By Bayley Vacation Rentals
3 2
apartment , Scarborough
This Pine Point, Scarborough flat is a short 0.3km stroll from a 6.4km-long beach, near Bayley's Lobster Pound and The Bait Shed, and conveniently located for the trolley to Old Orchard Beach. The 102 square metre self-catering property sleeps six, boasting three bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a three-season porch, propane grill, wood firepit, and four parking spaces.
9.2 7 reviews
Portland, ME
12/07 – 14/07
£655/nighttotal: £1310 (2 )
Luxe Coastal Retreat With Hot Tub & Fire Pit
4 2
apartment , Portland
This luxurious Portland apartment, situated in the North Deering neighbourhood, offers easy access to Westbrook College Historic District and the Tate House Museum, with Mackworth Island State Park and Little John Island Preserve also nearby. The 269 square metre (approximately 2890 square feet) property boasts four bedrooms, six bathrooms, and accommodates up to ten guests, featuring a fully equipped chef's kitchen, jacuzzi, terrace, garden, parking and oceanfront views.
9.9 675 reviews
Portland, ME
13/11 – 15/11
£185/nighttotal: £370 (2 )
Historic Home In The West End. Private Parking.
1 2
apartment , Portland
This charming apartment is situated in the Old Port district of Portland, a short walk from the Portland Museum of Art and State Theater. It has received excellent ratings for its location, cleanliness, and overall experience. The flat offers two bedrooms and can accommodate up to three guests. It features a well-equipped kitchenette, a private bathroom, and thoughtful touches like a coffee maker, tea kettle, and stemware.
9.9 366 reviews
Portland, ME
13/11 – 15/11
£1252/nighttotal: £2504 (2 )
Newly Renovated, Classy, And Elegant!
5 2
apartment , Portland
This stylish flat is located just a short distance from downtown Portland, making it easy to explore the city's attractions and amenities. It has consistently received excellent ratings for cleanliness, location, and overall experience. The two-bedroom flat comfortably accommodates couples or small families. It comes equipped with a modern kitchen, a comfortable living area with a large TV, and a private terrace, making it a great choice for a relaxing stay.
Discover Self-Catering Rentals with a Pool in Portland, ME
A holiday rental or Airbnb with a swimming pool near the water in Portland, ME is a brilliant base for a relaxing swim. View our collection.
9.9 164 reviews
Portland, ME
15/09 – 18/09
£379/nighttotal: £1137 (3 )
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
1 4
apartment , Portland
This three-bedroom house is located just 5 kilometres from downtown Portland, offering easy access to the city's attractions, including restaurants, breweries, and wineries. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The house can accommodate up to eight guests and features a fully equipped kitchen, a private garden, and a swimming pool, perfect for relaxing and enjoying the outdoors. Guests can also benefit from amenities like air conditioning, free Wi-Fi, and parking.
10 9 reviews
Portland, ME
12/09 – 19/09
£1332/nighttotal: £9324 (7 )
Peaks Island Oceanfront Escape: Private Pool & A/c
1 4
apartment , Portland
This charming house is located on Peaks Island, just a short ferry ride from Portland, offering stunning ocean views and a peaceful escape from the city. The island is a popular destination for families and couples looking for a relaxing getaway, with plenty of walking trails, beaches, and restaurants to explore. This spacious house has four bedrooms and two bathrooms, comfortably accommodating up to ten guests. Enjoy the private pool, wrap-around porch, and fully equipped kitchen, along with the convenience of concierge services for grocery stocking and golf cart rentals.
10 98 reviews
Portland, ME
26/06 – 28/06
£473/nighttotal: £946 (2 )
Luxury Retreat In Back Cove | 10 Min To Downtown
1 1
apartment , Portland
This studio apartment is located in the Back Cove neighbourhood of Portland, a peaceful residential area just 3.2 kilometres from the city centre. It has received excellent ratings for cleanliness, location and user experience. The apartment is a one-bedroom studio, ideal for a couple, featuring a spacious open floor plan with three large dormers, exposed collar ties and oversized windows. The studio is equipped with a kitchenette, a king-sized bed, a marble rain shower, a deep soaking tub, a garden, a swimming pool and a fitness centre.
8.7 7 reviews
Portland, ME
07/09 – 12/09
£314/nighttotal: £1570 (5 )
Good Vibes Portland Home - 4 Wonderful Seasons
3 2
house , Portland
This holiday home is located in Portland, just 5 kilometres from the Portland Observatory and 27 kilometres from Funtown Splashtown USA. This makes it a great base for exploring the city and the surrounding area. The property is a 3-bedroom house, with a floor area of 134 square metres, and can accommodate up to 15 guests. It comes with a private pool, a fully equipped kitchen, a garden, parking, and a washing machine.
Frequently asked questions about holiday rentals in Portland, ME
What are the top family-friendly attractions in Portland, ME?
The Portland Museum of Art is a great place to visit with kids, and the Children's Museum & Theatre of Maine is always a hit. For some outdoor fun, head to the Eastern Promenade, which has a playground and scenic walking paths. And don't forget to visit the Portland Head Light, the oldest lighthouse in Maine.
What are the best Airbnb and holiday rentals in Portland, ME?
When is the best time to book a vacation rental in Portland, ME?
Summer is the busiest time in Portland, so if you're looking for the best deals, book your vacation rental in the shoulder seasons - spring or autumn. You'll still have great weather and fewer crowds.
What are the most popular Airbnbs in Portland, ME?
What events or festivals should visitors check out in and around Portland, ME?
The Maine Lobster Festival in Rockland is a must-see in August, and the Portland Food & Wine Festival in September is a great way to sample local cuisine. For a festive atmosphere, visit the Christmas by the Sea festival in December.
What are the best holiday rentals with a pool in Portland, ME?
What are the best budget-friendly activities in Portland, ME?
Take a stroll along the Eastern Promenade for panoramic views of the city and harbour. Visit the Portland Public Library, a beautiful building with free exhibits and events. And explore the many parks and green spaces, like Deering Oaks Park, for a relaxing and inexpensive afternoon.
What are the best rentals for families and kids in Portland, ME?
What are the best restaurants with local dishes in Portland, ME?
For a classic Maine lobster roll, try The Lobster Shack at Two Lights. If you're looking for something more upscale, Fore Street offers a seasonal menu with fresh, local ingredients. And for a casual, family-friendly option, head to Becky's Diner for a hearty breakfast.
What are the best rentals or Airbnbs with a jacuzzi in Portland, ME?
What are the best walking or cycling routes in Portland, ME?
The Eastern Promenade is a great option for a scenic walk or bike ride. The Eastern Promenade is a 1.5km long park with stunning views of Casco Bay. For a longer ride, try the Eastern Trail, which runs along the coast for 18km.
Are there pet-friendly attractions in Portland, ME?
Many of Portland's parks and green spaces are dog-friendly, including Deering Oaks Park and the Eastern Promenade. Some restaurants also have outdoor patios where you can bring your furry friend.
What are the benefits of choosing a vacation rental in Portland, ME?
Vacation rentals often offer more space and privacy than a hotel room. They can also be a more cost-effective option, especially for families or groups. And many vacation rentals are located in residential neighbourhoods, giving you a more authentic experience of the city.
What are the top sports attractions and facilities in Portland, ME?
Portland is home to the Portland Sea Dogs, a minor league baseball team. The Hadlock Field is a great place to catch a game. The city also has a number of other sports facilities, including the Cross Insurance Arena, which hosts a variety of events.
Destinations nearby
Best Portland, ME holiday rentals with a balcony
10 5 reviews
Portland, ME
17/11 – 19/11
£234/nighttotal: £468 (2 )
A Peaceful Oasis On Munjoy Hill: 1st Flr - 3br + Parking
3 2
apartment , Portland
This spacious three-bedroom flat in Portland's Munjoy Hill district is a five-minute walk from the Eastern Promenade and a fifteen-minute walk to the Old Port. This 139 square meter apartment accommodates six guests and offers a fully equipped kitchen, in-unit laundry, air conditioning, a private garden, and is family-friendly with provided amenities.
Portland, ME
14/08 – 16/08
£782/nighttotal: £1564 (2 )
Modern Waterfront Apt With Bay Views
1 3
apartment , Falmouth
This modern waterfront flat in Falmouth offers picturesque bay views and is situated 5 kilometres from Portland Observatory and 5.8 kilometres from Merrill Auditorium. This 1-bedroom, 1-bathroom apartment with a floor area of approximately 56 square metres accommodates up to three guests and features air conditioning, a private balcony, complimentary WiFi, a fully equipped kitchen with a dishwasher and microwave, and a washing machine, with hiking opportunities nearby.
9.6 24 reviews
Portland, ME
03/08 – 06/08
£565/nighttotal: £1695 (3 )
Portlands Best Ocean Views From A 40-foot Private Deck
2 2
apartment , Portland
This apartment is situated in Portland's East End, just a short walk from Fort Allen Park, the Eastern Promenade, and East End Beach, offering easy access to the area's attractions and a peaceful, scenic setting. It has received excellent reviews from previous guests, highlighting its comfortable interior and convenient location. The two-bedroom flat spans 111 square metres and comfortably accommodates four guests. It boasts a well-equipped kitchen, a spacious deck with stunning ocean views, and modern amenities for a comfortable stay, including air conditioning and internet access.
10 97 reviews
Portland, ME
09/10 – 12/10
£940/nighttotal: £2820 (3 )
Lovely Cape Elizabeth Family Home 3 To 5 Miles To Portland & Beaches 3,700sf A/c
5 3
apartment , Cape Elizabeth
This family-friendly holiday home is located in Cape Elizabeth, just 3 miles from Casco Bay and Crescent Beach State Park. It has received excellent ratings for user experience, location, and cleanliness. The property offers 5 bedrooms and can comfortably accommodate up to 8 guests in its 344 square metres of space. Enjoy the garden with barbecue grills, relax in the jacuzzi, or have fun in the dedicated arcade/game room.
Top-Rated Self-Catering Holiday Rentals with Free Parking in Portland, ME
Free on-site parking comes with these holiday rentals near the water in Portland, ME, letting you focus on the coast and local beaches.
8.0 6 reviews
Portland, ME
28/08 – 27/09
£364/nighttotal: £10920 (30 )
Spacious And Modern One Bedroom Apartment
1 2
apartment , Portland
This apartment is located on Valley Street, just a short walk from Casco Bay, Maine Medical Center, the Portland Exposition Building, and Deering Oaks Park, offering easy access to Portland's attractions and green spaces. The apartment has received very good ratings for user experience, location, and cleanliness. The apartment is a one-bedroom, one-bathroom flat with a floor area of 79 square metres and can accommodate up to three guests. It comes with a fully equipped kitchen, a washing machine, free Wi-Fi, a patio, a garden, parking, and air conditioning.
10 18 reviews
Portland, ME
12/07 – 14/07
£1332/nighttotal: £2664 (2 )
Westend Large Penthouse Walk To Old Port W/parking
4 1
apartment , Portland
This spacious West End Portland flat, a 10-minute walk (approximately 1.6km) from the Old Port, is situated in a historic 1848 Sea Captain Ingraham mansion, offering treetop and partial harbour views and proximity to the Congress Street and Arts District. The four-bedroom, three-bathroom penthouse sleeps ten guests, boasting dedicated off-street parking for two cars, a fully equipped kitchen (fridge, microwave), air conditioning, internet access, and a private office; nearby attractions include the Portland Museum of Art, State Theatre, Victoria Mansion, and Charles Q. Clapp House.
9.8 94 reviews
Portland, ME
18/08 – 22/08
£253/nighttotal: £1012 (4 )
Apartment In Arts District
1 2
apartment , Portland
This Portland Arts District apartment is a two-minute walk from the State Theatre and a kilometre from the Old Port, offering easy access to Portland Museum of Art and the Cumberland Club. The self-contained studio flat, sleeping two, features a king-size bed, fully equipped kitchenette (fridge, freezer, microwave), air conditioning, parking, and blackout shades; it overlooks a garden and is situated above a restaurant and bar.
8.9 67 reviews
Portland, ME
07/09 – 12/09
£399/nighttotal: £1995 (5 )
Nature With In-town Living That Feels A World Away. May-june-july Special!!!
3 2
apartment , Portland
This Portland vacation home is conveniently located in Stroudwater, just a short distance from the Tate House Museum and Casco Bay, offering easy access to both historical and scenic attractions. It has received consistently high ratings for its cleanliness, location, and overall experience. The property has three bedrooms and can accommodate up to six guests, spanning 204 square metres. It comes equipped with a range of amenities including a fully equipped kitchen, air conditioning, a garden, and parking, ensuring a comfortable and enjoyable stay.
