Holiday Rentals in Portland, ME

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Portland, ME holiday rentals
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Best Holiday rentals and Airbnb offers in Portland, ME

Best family friendly Portland, ME holiday rentals

Among the 959 accommodations in Portland, ME, here are the 4 best family friendly rentals

Captain’s Quarters Seaside Cottage - Portland, ME
10 20 reviews
Portland, ME
18/08 – 22/08
SG$651/nighttotal: SG$2604 (4 )

Captain’s Quarters Seaside Cottage

1 2
apartment , Falmouth
This Falmouth Flats cottage, a short distance (approximately 0.8 km) from the ocean and a few minutes' drive from Portland's city centre, offers easy access to both coastal walks and urban attractions.
The two-bedroom, one-bathroom holiday home sleeps three guests and includes a fully equipped kitchen with dishwasher, air conditioning, garden, parking, and excellent guest reviews; enjoy nearby Falmouth beaches and Portland's culinary scene.
Private House! 7 Min To Oldport! Walk To Ocean! - Portland, ME
9.8 278 reviews
Portland, ME
21/08 – 23/08
SG$2732/nighttotal: SG$5464 (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.
Renovated Old Port 2br Loft, Waterfront & Shops - Portland, ME
8.3 10 reviews
Portland, ME
03/08 – 06/08
SG$995/nighttotal: SG$2985 (3 )

Renovated Old Port 2br Loft, Waterfront & Shops

2 2
apartment , Portland
This Portland apartment, a stylishly renovated loft, is located in the Old Port district, a 2km walk from East End Beach and 5km from Portland International Jetport.
The 79 square metre property features two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with a fridge and dishwasher, free Wi-Fi, and air conditioning.
2br Apt | Full Kitchen | 10 Min To Old Port - Portland, ME
9.8 453 reviews
Portland, ME
09/10 – 12/10
SG$596/nighttotal: SG$1788 (3 )

2br Apt | Full Kitchen | 10 Min To Old Port

1 3
apartment , Portland
This Oakdale neighbourhood apartment in Portland, Oregon, is conveniently located near Whole Foods, Trader Joe's, and Hannaford's supermarkets, with new restaurants within walking distance.
This 111-square-metre (1194 sq ft) two-bedroom, two-bathroom dwelling, renovated from an 1891 historic home, sleeps six guests and boasts off-street parking for two cars, a private keypad entry, a restored clawfoot tub, a smart TV with Netflix and Sling, and a covered porch with garden access.

Best Portland, ME holiday rentals with a pool

Among the 959 accommodations in Portland, ME, here are the 4 best rentals with a pool

Good Vibes Portland Home - 4 Wonderful Seasons - Portland, ME
8.7 7 reviews
Portland, ME
07/09 – 12/09
SG$542/nighttotal: SG$2710 (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.
Tower Suite Plus: Hot Tub, W/d, Parking, Spa Bath - Portland, ME
9.9 77 reviews
Portland, ME
12/09 – 19/09
SG$536/nighttotal: SG$3752 (7 )

Tower Suite Plus: Hot Tub, W/d, Parking, Spa Bath

1 4
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.
There's No Place Like Home - Portland, ME
9.7 117 reviews
Portland, ME
16/07 – 20/07
SG$514/nighttotal: SG$2056 (4 )

There's No Place Like Home

3 2
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.
Luxury Oceanfront Falmouth Estate On Casco Bay - Portland, ME
10 3 reviews
Portland, ME
27/06 – 01/07
SG$7615/nighttotal: SG$30460 (4 )

Luxury Oceanfront Falmouth Estate On Casco Bay

1 4
apartment , Falmouth
This luxurious waterfront property is located in Falmouth, Maine, just a short distance from the charming town centre. The house enjoys breathtaking views of Casco Bay and direct access to the water.
This spacious home has six bedrooms and ten bathrooms, comfortably accommodating up to fifteen guests. Guests can enjoy a range of amenities including a gourmet kitchen, an indoor pool, a jacuzzi, a sauna, a tennis court, a dockhouse with stunning views, and a fully stocked bar.

Frequently asked questions about holiday rentals in Portland, ME

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

    You have to visit the Portland Head Light, it's the oldest lighthouse in Maine and offers stunning views of the Atlantic Ocean. A stroll along the Eastern Promenade is also a must, it's a beautiful park with panoramic views of the city and harbour. And don't forget to check out the Old Port, a historic district with cobblestone streets, shops, and restaurants.
  • What are the best Airbnb and vacation rentals in Portland, ME?

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

    The Old Port is a popular choice for vacation rentals, as it is close to the harbour, restaurants, and shops. If you prefer a quieter neighbourhood, consider the West End, which has a more residential feel and is close to parks and beaches.
  • What are the most popular Airbnbs in Portland, ME?

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

    The Portland Museum of Art is a great option for families, with interactive exhibits and family-friendly programmes. The Children's Museum and Theatre of Maine is another popular choice, with hands-on exhibits and performances. For outdoor fun, head to the Eastern Promenade or the Portland Parks and Recreation Department's many playgrounds.
  • 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 peak season for tourism in Portland is from June to August, so book your vacation rental early if you're planning to visit during those months. You can often find good deals on rentals during the shoulder seasons, from April to May and September to October.
  • What are the best rentals for families and kids in Portland, ME?

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

    Take a walk along the Eastern Promenade, it's a beautiful park with panoramic views of the city and harbour. Visit the Portland Public Library, it's a beautiful building with free events and exhibitions. Explore the Old Port, a historic district with cobblestone streets, shops, and restaurants.
  • 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 on the Pier or Eventide Oyster Co. For a taste of Maine's culinary scene, head to Fore Street or The Honey Paw. And don't forget to try a Maine blueberry pie at one of the many local bakeries.
  • What are the best walking or cycling routes in Portland, ME?

    The Eastern Promenade offers a scenic 3.5 km walking path with views of the city and harbour. The Eastern Promenade Trail is a popular cycling route, with a mix of paved and unpaved paths. The Portland Trails network offers a variety of walking and cycling trails throughout the city.
  • Are there pet-friendly attractions in Portland, ME?

    Many of Portland's parks are dog-friendly, including the Eastern Promenade and Deering Oaks Park. The Portland Museum of Art also welcomes well-behaved dogs on a leash. Some restaurants have outdoor seating that is pet-friendly.
  • What are the benefits of choosing a vacation rental in Portland, ME?

    Vacation rentals offer more space and privacy than hotels. They also often come with amenities that are not typically found in hotels, such as kitchens and laundry facilities. And they can be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Portland, ME?

    The Portland Sea Dogs, a minor league baseball team, play their home games at Hadlock Field. The Portland Pirates, a minor league hockey team, play at the Cross Insurance Arena. The University of Southern Maine also has a variety of athletic facilities, including a track and field stadium.

Destinations nearby

Best Portland, ME holiday rentals with a balcony

Waterfront Two Master Suite Penthouse With Rooftop - Portland, ME
10 197 reviews
Portland, ME
21/09 – 24/09
SG$1843/nighttotal: SG$5529 (3 )

Waterfront Two Master Suite Penthouse With Rooftop

2 2
apartment , Portland
This penthouse apartment is situated on Portland's working waterfront in the Old Port district, just a short walk from the bustling Dimillo's Marina and within easy reach of local shops and restaurants. The property has received excellent user ratings for its location and amenities.
The apartment has two bedrooms and three bathrooms, providing space for up to four guests, and covers 158 square metres. It is fully equipped with modern conveniences, including a rooftop deck with stunning views, a well-equipped kitchen, and a Jacuzzi, making it an ideal choice for a comfortable and enjoyable stay in Portland.
Enjoy The Good Life. Free Parking, Ac In Bedroom. - Portland, ME
Portland, ME
25/08 – 29/08
SG$1036/nighttotal: SG$4144 (4 )

Enjoy The Good Life. Free Parking, Ac In Bedroom.

1 2
apartment , Portland
This Portland flat is situated 7 minutes' walk from the Portland Museum of Art and 1.4 kilometres from the historic Portland Downtown Historic District, offering convenient access to local attractions.
This 37 square metre apartment accommodates two guests with one bedroom and one bathroom, featuring air conditioning, a private balcony, complimentary Wi-Fi, and a kitchen equipped with a fridge, microwave, and dishwasher.
Ocean Front Estate. 15 Min To Portland. - Portland, ME
9.6 7 reviews
Portland, ME
08/08 – 12/12
SG$6602/nighttotal: SG$831852 (126 )

Ocean Front Estate. 15 Min To Portland.

5 1
apartment , Scarborough
This Scarborough holiday home is located just a 15-minute walk from Casco Bay and Higgins Beach, offering easy access to the beautiful coastline. It has received excellent guest reviews, making it a popular choice for families and groups.
The property is spacious, with 929 square metres of floor space and capacity for up to 10 guests. It offers a range of amenities, including a private pool, fitness centre, and a garden with barbecue facilities, providing plenty of opportunities for relaxation and entertainment.
2br W/ Parking | 5 Min To Downtown - Portland, ME
Portland, ME
21/09 – 24/09
SG$582/nighttotal: SG$1746 (3 )

2br W/ Parking | 5 Min To Downtown

2 2
apartment , Portland
This downtown Portland flat offers a prime location, situated a 12-minute walk from Fitzpatrick Stadium and a 10-minute walk from Deering Oaks Park, providing convenient access to local attractions.
This pet-friendly two-bedroom apartment accommodates up to six guests with air conditioning, complimentary Wi-Fi, a fully equipped kitchen, and on-site parking.

Best Portland, ME holiday rentals with parking

Chart House: Charming Three-bedroom Cape. - Portland, ME
9.9 36 reviews
Portland, ME
30/07 – 02/08
SG$893/nighttotal: SG$2679 (3 )

Chart House: Charming Three-bedroom Cape.

1 3
apartment , Falmouth
This Falmouth, Maine property, a three-bedroom Cape Cod-style house, is situated near the Presumpscot River, a short distance (precise distance in kilometres unavailable) from Falmouth town centre and local attractions.
The 1940s house offers a spacious layout with five downstairs rooms, two upstairs bedrooms (each with a queen-size bed and en-suite bathroom), a private patio, deck, gazebo, and grill; it sleeps six guests and includes a fully equipped kitchen, laundry facilities, ample off-street parking, and a fenced yard.
Modern & Sunny House Steps From The Promenade. Private Parking! - Portland, ME
10 42 reviews
Portland, ME
12/07 – 14/07
SG$888/nighttotal: SG$1776 (2 )

Modern & Sunny House Steps From The Promenade. Private Parking!

2 1
apartment , Portland
This Portland East End property is conveniently located a short walk from Casco Bay and the Portland Observatory, with the Maine Jewish Museum and the Cathedral of the Immaculate Conception within 1.6km.
The two-bedroom house, sleeping up to five guests, boasts a fully equipped kitchen, private patio, free Wi-Fi, on-site parking, and a spa; enjoy nearby waterfront activities and explore Portland's historical sites.
Historic Munjoy Hill Apartment, Just 3 Blocks From The Ocean & Pet-friendly! - Portland, ME
9.2 7 reviews
Portland, ME
03/08 – 06/08
SG$577/nighttotal: SG$1731 (3 )

Historic Munjoy Hill Apartment, Just 3 Blocks From The Ocean & Pet-friendly!

1 2
apartment , Portland
This dog-friendly apartment in Portland's Munjoy Hill neighbourhood is situated 0.5 km from the Eastern Promenade and 0.3 km from the Portland Food Co-op, within easy reach of local bars and restaurants such as Low Key.
The 88 square metre flat offers one bedroom, one bathroom, and sleeps six, featuring a fully equipped kitchen, private garden, spa, parking, air conditioning, internet access and a safe space.
Charming Modern West End Gem - Portland, ME
9.9 300 reviews
Portland, ME
20/10 – 23/10
SG$355/nighttotal: SG$1065 (3 )

Charming Modern West End Gem

2 4
apartment , Portland
This West End Portland flat is situated on a quiet residential street, approximately 1.6 kilometres from downtown Portland, offering easy access to shops and restaurants.
The two-bedroom, one-bathroom apartment sleeps four guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and stylish furnishings; nearby attractions include the city's many historical sites.
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