Holiday Rentals in Portland, ME

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Portland, ME holiday rentals
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1534 Holiday rentals and Airbnb in Portland, ME

Best family friendly Portland, ME holiday rentals

Among the 1534 accommodations in Portland, ME, here are the 4 best family friendly rentals

Quiet Family Vacation Home - Portland, ME
9.8 90 reviews

Quiet Family Vacation Home

apartment, Portland
This apartment is conveniently located in a peaceful neighbourhood just a few kilometres from Portland's bustling downtown area, offering easy access to nightlife, restaurants, and public transport. It consistently receives excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom flat comfortably accommodates up to four guests and features a fully equipped kitchen, a private patio with a barbecue, and air conditioning. Enjoy outdoor dining and relaxation in the garden, explore family-friendly attractions, and benefit from the convenience of on-site parking.
Beach Lovers' Dreamhouse - Portland, ME
10 22 reviews

Beach Lovers' Dreamhouse

apartment, South Portland
This South Portland house, a short walk from Willard Beach and Casco Bay, offers easy access to local shops, restaurants, and the coastal village atmosphere.
The two-bedroom, two-bathroom property sleeps four guests and includes a full kitchen with dishwasher, private off-street parking for two cars, a garden with outdoor games, and air conditioning.
The 8th Maine Regiment Lodge And Museum - Portland, ME
8.4 43 reviews

The 8th Maine Regiment Lodge And Museum

resort, Portland
The Eighth Maine Regiment Lodge and Museum is located in Portland, Maine, a short distance from the ferry dock to Peak Island and a short drive from Portland Head Light. The lodge has received very good user ratings for cleanliness and an excellent rating for its location.
The lodge is housed in a historic building dating back to the 1800s, offering guests a unique glimpse into Portland's rich history. The lodge provides a range of amenities, including a library, terrace, business centre, gift shop, and access to a museum with a focus on military history.
Convenient Portland Home 3 Miles From Downtown - Portland, ME
9.9 75 reviews

Convenient Portland Home 3 Miles From Downtown

apartment, Portland
This house is located in a peaceful residential neighbourhood in Portland, just a few kilometres from the waterfront, downtown, the historic Old Port, and Maine coastal beaches. It has excellent user, location, and cleanliness ratings.
This three-bedroom home comfortably accommodates up to seven guests and features a modern kitchen with a fridge, freezer, microwave oven, and dishwasher. Guests can enjoy a range of amenities, including air conditioning, a garden, a fitness centre, parking, and a large deck perfect for summer evenings.

Best Portland, ME holiday rentals with a pool

Among the 1534 accommodations in Portland, ME, here are the 4 best rentals with a pool

Historic Bakery House On Great Diamond Island With Lots Of Charm - Portland, ME
9.0 2 reviews

Historic Bakery House On Great Diamond Island With Lots Of Charm

apartment, Portland
This three-bedroom, two-bathroom flat in Portland is located a convenient 6-minute drive from Sand Beach and offers proximity to Sand Beach, Thompson's Point, and Higgins Beach, with major Portland landmarks such as the State Theatre and Portland Head Light also easily accessible.
This family-friendly apartment provides Wi-Fi, a full kitchen, a washer and dryer, access to a communal swimming pool and garden, and a private terrace, making it ideal for outdoor activities like hiking, biking, kayaking, bird watching, and boating for up to six guests.
Poolside Suite-gateway To Portland - Portland, ME
10 123 reviews

Poolside Suite-gateway To Portland

apartment, Falmouth
This one-bedroom apartment is situated in Falmouth, Maine, just a short walk from Mackworth Island and a 7-minute drive from Portland's Old Port, making it a convenient base for exploring the area. The apartment has received excellent ratings for cleanliness, location, and overall experience.
The self-contained unit comfortably accommodates two guests and features a private deck overlooking the pool, providing a relaxing outdoor space. Amenities include a Peloton bike, high-speed internet, streaming services, beach chairs, and homemade treats.
Modern Portland House - Minutes To The Old Port! - Portland, ME
10 16 reviews

Modern Portland House - Minutes To The Old Port!

apartment, Portland
This three-bedroom house in a residential area of Portland offers a quiet retreat just a few minutes' drive from the historic Old Port's dining and nightlife.
This property features a rare backyard swimming pool, a large deck with a grill, and private driveway parking, accommodating up to six guests with seasonal pool access from early June.
Backyard Paradise - Portland, ME
9.5 88 reviews

Backyard Paradise

apartment, Portland
This waterfront property is ideally located in Portland, within easy reach of attractions like the Tate House Museum and Casco Bay, and just a short drive from the Children's Museum and Theatre of Maine. The accommodation has consistently received excellent ratings for its location, cleanliness, and overall experience.
This three-bedroom house comfortably accommodates up to seven guests. The property offers a range of amenities, including a private pool, a spacious garden, and a modern kitchen, perfect for families or groups looking for a relaxing and enjoyable stay.

Frequently asked questions about holiday rentals in Portland, ME

  • What should a first-time visitor not miss in Portland, ME?

    You definitely want to visit the Old Port, it's the historic heart of the city with cobblestone streets, shops, and restaurants. If you're into art, the Portland Museum of Art is a must-see. And for stunning views, head to the Eastern Promenade, a park overlooking the harbour.
  • What are the best Airbnb and holiday rentals in Portland, ME?

  • Which neighborhood in Portland, ME should you consider for a vacation rental?

    The Old Port is a popular choice for its central location and proximity to attractions. If you prefer a quieter vibe, the West End is a charming neighbourhood with Victorian architecture and tree-lined streets. For a more modern feel, the Bayside area offers waterfront views and trendy restaurants.
  • What are the most popular Airbnbs in Portland, ME?

  • What are the top family-friendly attractions in Portland, ME?

    The Children's Museum & Theatre of Maine is a great place for kids of all ages. The Portland Science Center is another hit, with interactive exhibits. And for a day out in nature, the Eastern Promenade offers scenic views and walking trails.
  • What are the best holiday rentals with a pool in Portland, ME?

  • When is the best time to book a vacation rental in Portland, ME?

    Portland is busiest during the summer months, from June to August, so booking in advance is essential. If you're looking for a more affordable trip, consider visiting during the shoulder seasons, spring or autumn. You'll still have plenty to see and do, but the crowds will be smaller.
  • What are the best rentals for families and kids in Portland, ME?

  • What are the best budget-friendly activities in Portland, ME?

    A stroll along the Eastern Promenade offers stunning views for free. The Portland Public Library is a beautiful building with free events and exhibits. And you can enjoy a picnic at the park or on the waterfront.
  • What are the best rentals or Airbnbs with a jacuzzi in Portland, ME?

  • What are the best restaurants with local dishes in Portland, ME?

    For fresh seafood, try The Lobster Shack at Two Lights. For a classic Maine meal, head to The Fore Street Restaurant. And for a taste of the city's vibrant food scene, check out the Portland Food Tours.
  • What are the best walking or cycling routes in Portland, ME?

    The Eastern Promenade is a great walking route with stunning views of the city and harbour. The Eastern Promenade is also a popular spot for cycling. For a longer ride, the Eastern Trail is a paved path that stretches for 14 km along the coast.
  • Are there pet-friendly attractions in Portland, ME?

    The Eastern Promenade is a great place to walk your dog, and many restaurants and shops in the Old Port welcome well-behaved pets. The Portland Museum of Art also allows dogs on a leash.
  • What are the top sports attractions and facilities in Portland, ME?

    The Portland Sea Dogs, the city's minor league baseball team, play at Hadlock Field. The Cross Insurance Arena hosts concerts and other events, and the University of Southern Maine also has a variety of sports facilities.

Popular destinations

Best Portland, ME holiday rentals with a balcony

A Peaceful Oasis On Munjoy Hill: 1st Flr - 3br + Parking - Portland, ME
10 8 reviews

A Peaceful Oasis On Munjoy Hill: 1st Flr - 3br + Parking

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.
Luxury On Back Cove - Three Gables - Portland, ME
9.7 4 reviews

Luxury On Back Cove - Three Gables

apartment, Portland
This Portland flat is a 19-minute walk from the Arts District and 4.2 kilometres from Merrill Auditorium, with Portland International Jetport Airport 4 kilometres away.
This 93 square metre, three-bedroom, two-bathroom apartment sleeps up to eleven guests and offers a private balcony, a garden, air conditioning, and complimentary WiFi, with a kitchen equipped with a fridge, microwave, and dishwasher.
Munjoy Hill Hideaway With Ac - Walk To Dining & Eastern Promenade - Portland, ME
8.6 31 reviews

Munjoy Hill Hideaway With Ac - Walk To Dining & Eastern Promenade

apartment, Portland
This one-bedroom flat is situated in Portland's Munjoy Hill district, within 800 meters of the Eastern Promenade and a short walk to local bakeries and restaurants.
This 69 square meter flat accommodates two guests and features a well-equipped kitchen, air conditioning, a deck, and parking, with easy access to the Casco Bay Ferry and the historic Old Port.
Walk To Willard Beach - Portland, ME
No reviews

Walk To Willard Beach

house, South Portland
This South Portland property offers a detached house for rent, ideally situated a minute's walk from Willard Beach, 22.5 kilometres from Funtown Splashtown USA, and 6.3 kilometres from Merrill Auditorium.
This detached house boasts a 400 square metre floor area, accommodating up to two guests with one bedroom and one bathroom, and features a fully equipped kitchen with a dishwasher and oven, air conditioning, a terrace, garden, and complimentary WiFi.

Best Portland, ME holiday rentals with parking

Sun-lit Family Friendly Home In Munjoy Hill - Portland, ME
9.8 69 reviews

Sun-lit Family Friendly Home In Munjoy Hill

apartment, Portland
This Munjoy Hill house, in Portland, Maine, offers a unique location near the Eastern Promenade and Portland Observatory, with convenient proximity to a sauna, kombucha brewery, bakery, and coffee shop.
The two-bedroom, two-bathroom property sleeps five guests comfortably, featuring a fully equipped kitchen, in-unit laundry, keyless entry, and private parking; nearby activities include exploring the Eastern Promenade and visiting the Portland Observatory.
Arlie's Digs! - One Block To Willard Beach! - Portland, ME
9.8 77 reviews

Arlie's Digs! - One Block To Willard Beach!

apartment, South Portland
This ground-floor flat is located in Willard Square, a short walk from Portland's beach and Scratch Bakery, and within 2 kilometres of the Portland Headlight, Fort Williams Park, and the Old Port. The accommodation has received excellent ratings for cleanliness, location, and user experience.
The flat is spacious with two bedrooms, a living room with seating for six, and a separate dining room. It offers a fully equipped kitchen, a private deck with a table and chairs, access to a large, grassy backyard, and dedicated parking for two cars.
The Highland House - Portland, ME
9.9 49 reviews

The Highland House

apartment, Portland
This Portland house, centrally located but with unspecified distances to landmarks, offers a convenient base for exploring the city.
The four-bedroom, one-bathroom property sleeps six guests and boasts a fully equipped kitchen, modern entertainment systems, high-speed internet, and a south-facing deck; making it ideal for family getaways or group trips.
Charming, Single-family Home - Munjoy Hill, Ocean - Portland, ME
10 59 reviews

Charming, Single-family Home - Munjoy Hill, Ocean

house, Portland
This charming three-bedroom house is located in the Munjoy Hill neighbourhood, just 0.8 km from the Eastern Promenade and the ocean, offering stunning views and easy access to walking and cycling trails. The property has consistently received excellent user ratings for its location, cleanliness, and overall experience.
The house is spacious and comfortable, accommodating up to four guests, and features a well-equipped kitchen, three bathrooms, and a private deck and patio. Guests can enjoy the modern in-home theatre, a wood-burning stove, bikes for exploring the neighbourhood, and a unique lower level designed for relaxation and work.
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