Vacation Rentals in Portland, ME

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Portland, ME vacation rentals
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1534 Vacation rentals and Airbnb in Portland, ME

Best family friendly Portland, ME vacation rentals

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

Cape Elizabeth Home Close To Portland & Beaches! - Portland, ME
10 100 reviews

Cape Elizabeth Home Close To Portland & Beaches!

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.
Renovated Ranch 5 Bed 2 Bth, Open Concept. Close To Beaches, Airport & Portland - Portland, ME
9.6 15 reviews

Renovated Ranch 5 Bed 2 Bth, Open Concept. Close To Beaches, Airport & Portland

apartment, Scarborough
This five-bedroom farmhouse is situated just a short drive from Scarborough town centre, offering easy access to the area's beaches, airport and Portland. The property has received excellent reviews from previous guests, suggesting a comfortable and enjoyable stay.
The farmhouse is ideal for families and groups, with space for up to 12 guests. The property boasts a spacious backyard, woodland trails, a fully equipped kitchen, luxury amenities and access to a range of outdoor activities, including hiking, biking and skiing within 72 kilometres.
5 Star Back Cove Apartment With Water View! - Portland, ME
10 164 reviews

5 Star Back Cove Apartment With Water View!

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.
Lovely 3bdrm Home W/ Ac & Bbq 10min To Dt Portland - Portland, ME
9.8 210 reviews

Lovely 3bdrm Home W/ Ac & Bbq 10min To Dt Portland

apartment, Portland
This spacious Portland house, a 6.4km drive from downtown Portland's attractions, offers easy access to the city's amenities.
Sleeping up to eight guests, this three-bedroom, two-bathroom property boasts a fully-fenced garden with firepit and BBQ, a well-equipped kitchen including a double oven and dishwasher, and high-speed Wi-Fi.

Best Portland, ME vacation rentals with a pool

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

Maine Hacienda W/hot Tub & Seasonal Pool - Portland, ME
10 285 reviews

Maine Hacienda W/hot Tub & Seasonal Pool

apartment, Portland
This one-bedroom apartment is situated at the foot of Deering Highlands, a short walk from Woodford's Corner and Forest Avenue, with a 10-minute drive to downtown Portland. It has received excellent ratings for location, cleanliness, and user experience.
The apartment is perfect for couples, offering a private and comfortable space with a modern maritime vibe. Guests can enjoy a range of amenities including a seasonal pool, a year-round hot tub, a well-equipped kitchen, and dedicated off-street parking.
Tower Suite Plus: Hot Tub, Pool, Parking, Spa Bath - Portland, ME
10 84 reviews

Tower Suite Plus: Hot Tub, Pool, Parking, Spa Bath

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.
Coastal Island Retreat In Diamond Cove, Casco Bay - Portland, ME
10 2 reviews

Coastal Island Retreat In Diamond Cove, Casco Bay

house, Portland
This island dwelling on Diamond Cove offers a 30-minute ferry journey to Portland's Old Port and is near historic Fort McKinley.
The 241-square-metre property accommodates six guests across three bedrooms and two bathrooms, featuring a well-equipped kitchen, air conditioning on the ground floor, and access to communal amenities including a swimming pool.
Back Yard Paradise - Portland, ME
9.5 86 reviews

Back Yard 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've got to check out the Old Port, it's right on the waterfront and full of shops, restaurants and historic buildings. A walk along the Eastern Promenade is a must for its views of the harbour and Casco Bay. And don't forget to visit the Portland Museum of Art, it's got a great collection of American art.
  • What are the best Airbnb and vacation rentals in Portland, ME?

    Inn At Parkspring 5 | Self Check In | Parking, Private Oasis: 2 Apartments As 1 and Private Hill Top Apartment/w One Car Driveway are the most popular Airbnb and vacation rentals in Portland, ME among travelers.

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

    The Old Port is a great option for a vacation rental, it's right in the heart of the action and you're within walking distance of everything. If you want something quieter, consider the West End, it's a bit further out but still close to the city centre and has some lovely Victorian homes.
  • What are the most popular Airbnbs in Portland, ME?

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

    The Portland Children's Museum is a great place to take the kids, they'll love all the interactive exhibits. The Maine State Aquarium is also a popular choice, it's home to a variety of marine life. And for a bit of outdoor fun, head to the Eastern Promenade, there's plenty of space to run around and enjoy the views.
  • What are the best vacation rentals with a pool in Portland, ME?

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

    The best time to book a vacation rental in Portland is during the shoulder seasons, from April to May and September to October. You'll get the best deals and the weather is still pleasant. Of course, if you want to experience the summer festivals, you'll need to book in advance.
  • What are the best rentals for families and kids in Portland, ME?

  • What events or festivals should visitors check out in and around Portland, ME?

    The Maine Lobster Festival in Rockland is a real highlight, it's held every August and is a huge celebration of all things lobster. The Portland Food and Wine Festival in September is another great event, with food stalls, cooking demonstrations and wine tastings. And for a bit of local culture, check out the Portland International Film Festival in February.
  • 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 a taste of Maine, try the lobster roll at The Lobster Shack at Two Lights. If you're looking for something a bit more upscale, try Fore Street, they have a great menu of seasonal New England dishes. And for a casual meal, check out The Holy Donut, they have some delicious and unique donut flavours.
  • What are the best walking or cycling routes in Portland, ME?

    The Eastern Promenade is a great place for a walk or a bike ride, it offers stunning views of the harbour and Casco Bay. The Eastern Promenade is also a great place for a walk or a bike ride, it offers stunning views of the harbour and Casco Bay. The Eastern Promenade is also a great place for a walk or a bike ride, it offers stunning views of the harbour and Casco Bay.
  • Are there pet-friendly attractions in Portland, ME?

    Many of the parks and green spaces in Portland are pet-friendly, including the Eastern Promenade and the Portland Public Library. There are also a number of pet-friendly restaurants and cafes, so you won't have to leave your furry friend behind.
  • 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, a beautiful stadium right in the heart of the city. If you're a hockey fan, check out the Portland Pirates, who play at the Cross Insurance Arena. And for a bit of outdoor fun, head to the Eastern Promenade, there's plenty of space for a game of frisbee or a picnic.

Popular destinations

Best Portland, ME holiday rentals with a balcony

Penthouse Two Master Waterfront Suite With Rooftop - Portland, ME
10 419 reviews

Penthouse Two Master Waterfront Suite With Rooftop

apartment, Portland
This penthouse suite is situated on Portland's working waterfront, overlooking Dimillo's Marina, a short walk from the Old Port and within easy reach of the city's major attractions. It has been rated excellent for user experience, location, and cleanliness.
The apartment is a spacious 149 square metre two-bedroom property that can accommodate up to four guests. Its features include a jacuzzi, a terrace, a garden, parking, a fully equipped kitchen, and a washer/dryer.
Oakdale Area Nice Location - Portland, ME
8.3 3 reviews

Oakdale Area Nice Location

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.
Casco Bay Sunrise - Portland, ME
9.7 298 reviews

Casco Bay Sunrise

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.
Monument Garden Sweet - Portland, ME
9.9 733 reviews

Monument Garden Sweet

apartment, Portland
This apartment in Portland is conveniently located just a short walk from East End Beach and within easy reach of downtown attractions. It has been rated excellent for location, cleanliness, and user experience.
This spacious property has five bedrooms, making it ideal for large groups or families. It features a fully equipped kitchen, free parking, Wi-Fi, air conditioning, and a garden, ensuring a comfortable and enjoyable stay.

Best Portland, ME holiday rentals with parking

Portland Stately 3-br, 2.5 Ba | Walk To Back Cove - Portland, ME
No reviews

Portland Stately 3-br, 2.5 Ba | Walk To Back Cove

apartment, Portland
This historic three-bedroom flat is located in a distinguished Portland neighbourhood close to the Back Cove, offering convenient access within 500 metres of the Old Port's renowned restaurants, breweries, shops, and trails, and just a few kilometres from the city centre and waterfront.
This property for six guests features two en-suite bedrooms, a kitchen with a fridge, air conditioning, a jacuzzi, parking, and a sunny backyard, blending original period details with modern comforts for a pleasant stay.
Historic Seaside Cottage 5 Min From Portland! - Portland, ME
9.4 235 reviews

Historic Seaside Cottage 5 Min From Portland!

apartment, Falmouth
The Seaside Cottage Retreat is located in Falmouth, just a short drive from both downtown Portland and the scenic Mackworth State Park. The property enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This charming cottage offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy a private yard, full house access, and a kitchen equipped with modern appliances, perfect for preparing meals during your stay.
Skyline 138: Charming West End Mansard Penthouse - Portland, ME
9.2 36 reviews

Skyline 138: Charming West End Mansard Penthouse

apartment, Portland
This spacious Portland penthouse apartment, sleeping eight, is situated in the West End, a five-minute walk from the Western Promenade and Deering Oaks Park and fifteen minutes from the Old Port.
The 126 square metre dwelling boasts three bedrooms, one bathroom, a fully equipped galley kitchen, free Wi-Fi, on-street parking, and a balcony; nearby attractions include the Portland Museum of Art and Maine Medical Center.
Vibrant Bayside, Walk To All The Action. - Portland, ME
9.4 662 reviews

Vibrant Bayside, Walk To All The Action.

apartment, Portland
This Portland studio apartment enjoys a central location in downtown Portland, a 1.1km walk from the city centre, 2.4km from the Old Port, and just a short distance from Deering Oaks Park.
The ground-floor self-contained apartment sleeps two guests, features a full kitchen with fridge, freezer and microwave, air conditioning, free parking nearby, and includes Netflix and Hulu.