Best Holiday rentals and Airbnb offers in Portland, ME
9.8 66 reviews
Portland, ME
25/08 – 29/08
£244/nighttotal: £976 (4 )
Island View House Bnb Self Check-in/ Free Parking
1 2
apartment , Portland
This Munjoy Hill apartment in Portland, Maine, is a 15-minute walk (approximately 1.2km) from Fort Allen Park and Casco Bay, offering scenic harbour views and numerous restaurants and coffee shops within a 5-minute walk (approximately 0.8km). The self-catering flat features a king-size bed, free high-speed Wi-Fi, Netflix, Amazon Prime Video, private parking, and sleeps two guests in one bedroom and one bathroom.
8.8 6 reviews
Portland, ME
23/07 – 27/07
£191/nighttotal: £764 (4 )
Charming 2-bedroom House With Ac, Wifi In Lovely Falmouth
2 2
apartment , Falmouth
This Falmouth lakeside property offers private lakefront access with a dock, situated near Portland and its Old Port, though precise distances aren't specified. The two-bedroom house, sleeping up to five guests, includes a loft, WiFi, air conditioning, a spa, and a washer/dryer; nearby attractions include Sebago Lake and Thompson's Point.
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 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.
9.0 2 reviews
Portland, ME
12/07 – 14/07
£765/nighttotal: £1530 (2 )
Amazing West End Apartment Walkable To Downtown And The Waterfront.
2 1
apartment , Portland
This West End Portland apartment, a short walk from Casco Bay and Deering Oaks Park, offers easy access to the Portland Museum of Art and State Theatre. The two-bedroom, one-bathroom flat sleeps six, boasting Wi-Fi, air conditioning, and proximity to attractions such as Thompson's Point and Old Orchard Beach.
9.8 22 reviews
Portland, ME
03/07 – 06/07
£493/nighttotal: £1479 (3 )
In The Heart Of The Old Port
1 1
apartment , Portland
This Portland Old Port flat is centrally located in downtown Portland, Maine, within walking distance of shops, restaurants, and the ferry terminal for Casco Bay island excursions. The one-bedroom apartment, including a loft sleeping area, comfortably sleeps four guests and features a full kitchen, high-speed internet, and a designated workspace; nearby Fore Street Garage offers parking at £35 per day.
8.3 3 reviews
Portland, ME
14/08 – 16/08
£413/nighttotal: £826 (2 )
Oakdale Area Nice Location
2 3
apartment , Portland
This Portland Oakdale apartment offers convenient access to Merrill Auditorium (3.1km), Portland Observatory (3.8km), and Portland International Jetport (6km). The 93 square metre flat comprises two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, free Wi-Fi, private parking, and a balcony.
Portland, ME
10/07 – 13/07
£378/nighttotal: £1134 (3 )
Cozy West End, Walk To Old Port
2 4
apartment , Portland
This two-bedroom flat offers immediate access to Portland's historic West End, placing you steps from the Old Port and city centre, with the arts and culinary scene within easy reach. This 1880s residence, accommodating up to four guests, features a fully equipped eat-in kitchen, a comfortable lounge, and a recently updated bathroom, with parks and cafes nearby for your convenience.
9.9 79 reviews
Portland, ME
18/08 – 22/08
£341/nighttotal: £1364 (4 )
Tower Suite Plus: Hot Tub, Pool, Parking, Spa Bath
1 2
apartment , Portland
This charming apartment is situated in a historic Victorian house in Portland, just 6 kilometres from the city centre and 3 kilometres from the airport and train station. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment is spacious and comfortably accommodates up to four guests, with two bedrooms, a modern bathroom, and a lounge/kitchenette. Guests can enjoy access to a shared hot tub, outdoor fire pit, and a large garden with picnic tables, as well as a Level 2 EV charging station.
9.8 8 reviews
Portland, ME
19/10 – 24/10
£203/nighttotal: £1015 (5 )
Modern Comfort Meets Maine Charm.
3 4
apartment , Portland
This three-bedroom flat, ideal for up to four guests, is located in a quiet Portland neighbourhood, 2.5 kilometres from the Old Port's restaurants, shops, and breweries, and across from Baxter Woods for walking trails. This property offers air conditioning, Wi-Fi, and a kitchen with a microwave and freezer, serving as a convenient base for exploring Portland's waterfront and culinary scene.
9.9 558 reviews
Portland, ME
12/07 – 14/07
£948/nighttotal: £1896 (2 )
Old Port Penthouse Suite - Amazing Harbor Views
2 1
apartment , Portland
This penthouse apartment is located in Portland's Old Port district, directly across from the working waterfront, offering stunning views of the cityscape and harbour, and within walking distance of the Casco Bay Ferry, the popular Dimillos floating restaurant, and the award-winning Standard Baking bakery and Fore Street Restaurant. The accommodation has excellent user, location, and cleanliness ratings. The two-bedroom, two-bathroom apartment is 125 square metres and can comfortably sleep four guests. The property features a fully equipped kitchen, modern appliances, a spacious living area, and a private deck with breathtaking views.
9.9 57 reviews
Portland, ME
27/07 – 30/07
£933/nighttotal: £2799 (3 )
Back Cove 1st Floor 4 Bedroom, 1.5 Bath
4 9
apartment , Portland
This Portland apartment, located near Forest Avenue and Woodfords Corner, offers easy access to Back Cove and the University of Southern Maine, being a short 5-minute drive (approximately 3.2 km) from the Old Port. This spacious four-bedroom condo sleeps up to twelve guests, boasting a fully equipped kitchen, high-speed internet, off-street parking, and a private outdoor area with barbecue facilities; nearby attractions include the Back Cove Trail and The Great Lost Bear pub.
Search Coastal Holiday Rentals near Portland, ME
Experience relaxing maritime culture at coastal holiday rentals in Portland, ME, situated a short distance from popular beach communities.
9.0 19 reviews
Portland, ME
15/08 – 18/08
£918/nighttotal: £2754 (3 )
The Cove By Bayley Vacation Rentals
3 2
apartment , Scarborough
This family-friendly holiday home is located just a 3km walk from Pine Point Beach and Grand Beach, offering easy access to the beautiful Scarborough coastline. It has consistently received excellent user ratings, making it a popular choice for families seeking a comfortable and enjoyable stay. The property features three bedrooms and three bathrooms, spanning 104 square metres and comfortably accommodating up to eight guests. Enjoy the convenience of a fully equipped kitchen, a private patio, and a swimming pool, as well as the added benefit of air conditioning, free Wi-Fi, and parking.
Portland, ME
27/09 – 03/10
£974/nighttotal: £5844 (6 )
Salty Dolphin By Bayley Vacation Rentals
4 2
apartment , Scarborough
This family-friendly apartment in Scarborough's Pine Point district is a 5-minute walk from Pine Point Beach and a 6-minute drive from Old Orchard Beach, offering on-site parking and Wi-Fi. Spanning 171 square meters, this property accommodates up to 8 guests with 4 bedrooms and 3 bathrooms, featuring a full kitchen, air conditioning, a terrace with a barbecue, and a washer/dryer for a comfortable stay.
10 73 reviews
Portland, ME
06/10 – 09/10
£497/nighttotal: £1491 (3 )
Whole House On A Great Island In Casco Bay!
3 4
apartment , Long Island
Nona's View is a 45-minute ferry ride from Portland, Maine, offering easy access to the mainland while providing a peaceful escape on Long Island. The apartment has received excellent ratings for location, cleanliness, and overall experience. This three-bedroom, two-bathroom home can accommodate up to 10 guests. It offers a fully equipped kitchen, parking, internet access, and is pet-friendly, making it ideal for families or groups seeking a relaxing getaway.
9.9 837 reviews
Portland, ME
08/09 – 10/09
£464/nighttotal: £928 (2 )
Fabulous! Working Waterfront Views. 94 Walk Score.
1 1
apartment , Portland
This spacious apartment in Portland, Maine is located just a short walk from the Old Port, Arts District, and West End, placing you within easy reach of the city's main attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall guest experience. This three-storey home offers a combined 300 square metres of living space, making it ideal for larger groups. Guests can enjoy a modern kitchen with poured concrete countertops, access to a garden, and parking facilities.
Best family friendly Portland, ME holiday rentals
Among the 959 accommodations in Portland, ME, here are the 4 best family friendly rentals
9.8 17 reviews
Portland, ME
13/11 – 15/11
£342/nighttotal: £684 (2 )
Modern Lake House Close To Portland
3 2
apartment , Falmouth
This Falmouth lakeside property, situated within 14.5km of Riverside Municipal Golf Course, Casco Bay, and Westbrook College Historic District, offers tranquil views and convenient access to local attractions. This 93 square metre house sleeps six, boasting three bedrooms, one bathroom, a fully equipped kitchen, Wi-Fi, air conditioning, a terrace, garden, parking and BBQ facilities, perfect for family getaways or golfing breaks.
9.8 278 reviews
Portland, ME
21/08 – 23/08
£1586/nighttotal: £3172 (2 )
Private House! 7 Min To Oldport! Walk To Ocean!
1 7
apartment , Portland
This spacious apartment is located in the Munjoy Hill neighbourhood, just 7km from the city centre and 7km from the Old Port, offering easy access to Portland's attractions. It benefits from excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The property spans 167 square metres and comfortably accommodates up to 16 guests. It features a well-equipped kitchen, a swimming pool, a garden, a spa, a fitness centre, and parking, providing everything you need for a relaxing and enjoyable stay.
9.9 75 reviews
Portland, ME
17/11 – 19/11
£604/nighttotal: £1208 (2 )
Large, Light Filled 4 Bedroom House - Walk To Ocean And Ferry
4 2
apartment , Portland
Heron's Perch, situated on Peaks Island, a short ferry trip from Portland, Maine, is steps from a local market and ice cream shop, and a short cycle ride (approximately 1.6km) from the ocean. This 186 square metre property, a four-bedroom house sleeping up to twelve guests, boasts two living rooms, a fully equipped kitchen including dishwasher, a garden, parking, and a back deck with grill; all within easy access of Portland.
9.7 291 reviews
Portland, ME
12/09 – 19/09
£265/nighttotal: £1855 (7 )
City Amenities, Casco Bay Sunrises And Natural Beauty
1 4
apartment , Portland
This Portland, Maine apartment is situated near Back Cove, offering easy access to Mackworth Island, the Eastern Promenade, and Portland city centre (a 5-minute drive). The 93 square metre property boasts two bedrooms, one bathroom, sleeps six comfortably, and includes a terrace, garden, spa, fitness centre, parking, and stunning Casco Bay views.
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
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.
9.7 117 reviews
Portland, ME
29/07 – 31/07
£298/nighttotal: £596 (2 )
There's No Place Like Home
3 4
apartment , Portland
This apartment is situated in a peaceful neighbourhood, just a short drive from the bustling Old Port Waterfront and within easy reach of Freeport's outlets. The property has consistently received excellent ratings for its cleanliness, location, and overall experience. The apartment has three bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a well-equipped kitchen, air conditioning, a swimming pool, parking, and a relaxing outdoor deck, making it perfect for a comfortable and enjoyable stay in Portland.
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 17 reviews
Portland, ME
21/09 – 24/09
£765/nighttotal: £2295 (3 )
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches And Downtown Portland
3 2
apartment , Scarborough
This Scarborough holiday home, minutes from beaches and Portland's Old Port, offers easy access to attractions such as Thompson's Point and Old Orchard Beach. Sleeping five guests, this three-bedroom, one-bathroom property boasts a private solar-powered spa with a heated indoor fitness pool (90°F), hot tub, sauna, and fire pit, alongside a four-season sunroom, kitchen with dishwasher, and free internet access.
9.9 164 reviews
Portland, ME
03/07 – 06/07
£1079/nighttotal: £3237 (3 )
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 1
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.
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.
9.6 387 reviews
Portland, ME
28/06 – 04/07
£192/nighttotal: £1152 (6 )
The Royal Exotic Portland Downtown
1 2
apartment , Portland
This charming flat is situated in the historic West End of Portland, just a short walk from the city centre, restaurants, the ocean, bars and parks. The property has received excellent ratings for its cleanliness, location and overall experience. The flat is a one-bedroom, one-bathroom property that can accommodate up to six guests. The well-equipped kitchen includes a fridge, freezer, microwave oven and dishwasher, and the apartment also benefits from air conditioning, parking and free internet access.
10 33 reviews
Portland, ME
07/08 – 10/08
£366/nighttotal: £1098 (3 )
Beautiful New Apt On Top Of Munjoy Hill With Private Deck And Private Parking.
1 2
apartment , Portland
This Munjoy Hill apartment in Portland, Maine, is moments from Casco Bay and the Portland Observatory, with Eastern Promenade and the Maine Narrow Gauge Railroad Museum within 1.6km. The self-catering flat offers one bedroom, one bathroom, sleeps two, and includes a fully equipped kitchen, private patio, in-unit laundry, and access to on-site barbecues; enjoy stunning waterfront views and easy access to local attractions.
10 85 reviews
Portland, ME
31/07 – 03/08
£336/nighttotal: £1008 (3 )
Historic Maine Barn With Private Saltwater Hot Tub
1 2
farm , Cape Elizabeth
This charming converted barn, located just a few kilometres from Portland and the coast, offers a tranquil escape in the heart of Cape Elizabeth. With excellent user, location and cleanliness ratings, you can be sure of a comfortable and enjoyable stay. The cosy cottage has one bedroom and one bathroom, sleeping up to two guests. Enjoy a private deck, a large garden, and access to nearby walking trails, perfect for exploring the beautiful surroundings.
9.9 234 reviews
Portland, ME
12/07 – 14/07
£526/nighttotal: £1052 (2 )
Modern & Sunny East End House. Private Parking!
1 1
apartment , Portland
This Portland apartment, near the Eastern Promenade with its Casco Bay views, is conveniently located within a few hundred metres of numerous restaurants, cafes, and breweries. The two-bedroom, one-bathroom dwelling sleeps four, features a fully equipped kitchen including a dishwasher, offers private parking, and provides a Pack 'n Play and highchair upon request.
Find the Best Luxury Holiday Rentals in Portland, ME
Comfort, quality and a prime location; each luxury holiday rental or Airbnb in Portland, ME is selected with your relaxation in mind.
9.7 21 reviews
Portland, ME
27/06 – 04/07
£649/nighttotal: £4543 (7 )
Urban Oasis With Spa And Gardens In Portland.
3 2
bungalow , Portland
Best Portland, ME holiday rentals with a balcony
Portland, ME
12/07 – 14/07
£313/nighttotal: £626 (2 )
The Woodland Loft At Falmouth
2 2
house , Falmouth
Portland, ME
31/07 – 03/08
£1475/nighttotal: £4425 (3 )
Cozy Home In Westbrook Close To Beaches And Portland.
2 2
apartment , Westbrook
9.9 140 reviews
Portland, ME
21/09 – 24/09
£1070/nighttotal: £3210 (3 )
Penthouse Two Master Waterfront Suite With Rooftop
2 2
apartment , Portland
10 7 reviews
Portland, ME
26/09 – 03/10
£584/nighttotal: £4088 (7 )
Sea Glass - Peaks Island Backshore Oceanfront Cottage With Stunning Views!
3 2
apartment , Portland
Compare Dog-Friendly Self-Catering Rentals in Portland, ME
These dog-friendly holiday rentals and Airbnbs in Portland, ME feature outdoor showers and access to pet-welcoming beaches.
9.7 308 reviews
Portland, ME
07/09 – 12/09
£204/nighttotal: £1020 (5 )
Bright Spacious West End 2br With Parking
1 2
apartment , Portland
10 5 reviews
Portland, ME
27/09 – 03/10
£1581/nighttotal: £9486 (6 )
Spacious West End Penthouse | Great For Groups
5 2
apartment , Portland
9.6 45 reviews
Portland, ME
28/09 – 30/09
£316/nighttotal: £632 (2 )
Spacious 3 Br In Portland's Libbytown!
3 3
apartment , Portland
9.5 28 reviews
Portland, ME
14/08 – 16/08
£415/nighttotal: £830 (2 )
Usm Area. Great Location.
1 3
apartment , Portland
Our Favourite Self-Catering Rentals with a Hot Tub in Portland, ME
These holiday rentals near the water in Portland, ME come with a hot tub or jacuzzi, ideal for a private evening soak. Explore now.
9.9 50 reviews
Portland, ME
06/08 – 09/08
£604/nighttotal: £1812 (3 )
3 Br Portland Home W/hot Tub-8mins From Old Port
1 2
apartment , Portland
10 100 reviews
Portland, ME
25/08 – 29/08
£354/nighttotal: £1416 (4 )
Saint Lawrence Luxury Suite 1br Apartment Get Away
1 2
apartment , Portland
9.9 85 reviews
Portland, ME
05/08 – 08/08
£248/nighttotal: £744 (3 )
Majestic Sanctuary!!
2 2
apartment , Westbrook
9.9 130 reviews
Portland, ME
27/06 – 01/07
£877/nighttotal: £3508 (4 )
Bright, Spacious Home, New Kitchen, Hot Tub, Beautiful Art, Ev Charger
1 4
house , Portland
Guest-Favourite Holiday Rentals with a Spa in Portland, ME
Wellness travel to Portland, ME starts with a holiday rental that features a proper spa.
