Best South Portland Vacation Rentals
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Great deal
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Beach access
Arlies Digs One Block To Willard Beach
- Cookware/ Kitchen utensils
- Air conditioning
- Luggage storage
- Laundry
- Ironing facilities
- Garden area
Arlies Digs One Block To Willard Beach South Portland villa is situated 400 metres from Willard Beach Parking, featuring such comforts as Wi-Fi and a private parking lot.
Arlies Digs One Block To Willard Beach
- Cookware/ Kitchen utensils
- Air conditioning
- Luggage storage
- Laundry
- Ironing facilities
- Garden area
Arlies Digs One Block To Willard Beach
Arlies Digs One Block To Willard Beach South Portland villa is situated 400 metres from Willard Beach Parking, featuring such comforts as Wi-Fi and a private parking lot.
The Coastal Connection
The 220 m² The Coastal Connection Apartment South Portland offers proximity to such tourist attractions as Congregation Bet Ha'am Reform Synagogue, situated just 7 minutes' walk away. This spacious apartment features Wi-Fi, along with parking for guests travelling by car.
The Coastal Connection
The Coastal Connection
The 220 m² The Coastal Connection Apartment South Portland offers proximity to such tourist attractions as Congregation Bet Ha'am Reform Synagogue, situated just 7 minutes' walk away. This spacious apartment features Wi-Fi, along with parking for guests travelling by car.
Modern Getaway By The Sea
- Free parking
- Air conditioning
- Flat-screen TV
The 3-bedroom Modern Getaway By The Sea Villa South Portland, located around a 5-minute walk from the modest Maine Military Museum, can host up to 6 guests. Located approximately 3 km from Children's Museum and Theatre of Maine, the villa provides Wi-Fi and private parking.
Modern Getaway By The Sea
- Free parking
- Air conditioning
- Flat-screen TV
Modern Getaway By The Sea
The 3-bedroom Modern Getaway By The Sea Villa South Portland, located around a 5-minute walk from the modest Maine Military Museum, can host up to 6 guests. Located approximately 3 km from Children's Museum and Theatre of Maine, the villa provides Wi-Fi and private parking.
Cheap South Portland Vacation Rentals
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Beach access
Modern Coastal Retreat On Cottage Road
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
Staying at the 2-bedroom Modern Coastal Retreat On Cottage Road South Portland, guests can easily reach Portland Head Lighthouse, located approximately 25 minutes' walk away. With a maximum capacity of 8 guests, the holiday home offers a car park.
Modern Coastal Retreat On Cottage Road
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
Modern Coastal Retreat On Cottage Road
Staying at the 2-bedroom Modern Coastal Retreat On Cottage Road South Portland, guests can easily reach Portland Head Lighthouse, located approximately 25 minutes' walk away. With a maximum capacity of 8 guests, the holiday home offers a car park.
Forest City Oasis And Spa
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Ironing facilities
- Sauna
- Garden area
To enjoy your vacation in South Portland, stay at the spacious 2-bedroom Forest City Oasis And Spa South Portland apartment, which is 3.1 km from Commercial Street and within 10 minutes' drive of Old Port. Wi-Fi and parking are also available at the apartment.
The availability of a sauna at this apartment ensures a relaxing stay.
Forest City Oasis And Spa
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Ironing facilities
- Sauna
- Garden area
Forest City Oasis And Spa
To enjoy your vacation in South Portland, stay at the spacious 2-bedroom Forest City Oasis And Spa South Portland apartment, which is 3.1 km from Commercial Street and within 10 minutes' drive of Old Port. Wi-Fi and parking are also available at the apartment.
The availability of a sauna at this apartment ensures a relaxing stay.
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Beach access
Walk To Willard Beach
- 24-hour reception
- Air conditioning
- Luggage storage
- Heating
- Garden area
Situated merely a 9-minute stroll from Fort Preble, the 1-bedroom Walk To Willard Beach South Portland villa ensures a great leisure experience by offering fisheries. Offering Wi-Fi, the South Portland holiday home is located 2.8 km from Maine Jewish Museum.
Walk To Willard Beach
- 24-hour reception
- Air conditioning
- Luggage storage
- Heating
- Garden area
Walk To Willard Beach
Situated merely a 9-minute stroll from Fort Preble, the 1-bedroom Walk To Willard Beach South Portland villa ensures a great leisure experience by offering fisheries. Offering Wi-Fi, the South Portland holiday home is located 2.8 km from Maine Jewish Museum.
Pet Friendly Vacation Rentals South Portland
Sunny House, By The Beach, Minutes From Portland
- 24-hour reception
- Air conditioning
- Heating
- Garden area
Sunny House, By The Beach, Minutes From Portland South Portland villa, located 5 minutes' walk from Saint John the Evangelist Roman Catholic Church, can host up to 6 guests. Located 4.6 km from the Libby house "Victoria Mansion", the 3-bedroom holiday home provides Wi-Fi and a car park.
Sunny House, By The Beach, Minutes From Portland
- 24-hour reception
- Air conditioning
- Heating
- Garden area
Sunny House, By The Beach, Minutes From Portland
Sunny House, By The Beach, Minutes From Portland South Portland villa, located 5 minutes' walk from Saint John the Evangelist Roman Catholic Church, can host up to 6 guests. Located 4.6 km from the Libby house "Victoria Mansion", the 3-bedroom holiday home provides Wi-Fi and a car park.
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Guest favorite
Hallowell Rooming House
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
Located 2.8 km from Hallowell Reservoir, Historic Hallowell Aptviewshot Tubwalk Downtown hotel offers air-conditioned rooms about a 10-minute drive from Capitol Park. Overlooking the lake, the inn lies a few moments from Hallowell Antique Mall and includes a hot tub and a sauna.
The hotel is a perfect place for canyoning, fisheries, and darts.
Hallowell Rooming House
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
Hallowell Rooming House
Located 2.8 km from Hallowell Reservoir, Historic Hallowell Aptviewshot Tubwalk Downtown hotel offers air-conditioned rooms about a 10-minute drive from Capitol Park. Overlooking the lake, the inn lies a few moments from Hallowell Antique Mall and includes a hot tub and a sauna.
The hotel is a perfect place for canyoning, fisheries, and darts.
Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Golf centre
Staying at the 1-bedroom Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa, guests can visit Wiscasset Bay Gallery, which is just 100 metres away. Suitable for 2 guests, the Wiscasset holiday home offers hiking, mini golf, and cycling to diversify guests' leisure.
Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Golf centre
Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants
Staying at the 1-bedroom Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants Wiscasset villa, guests can visit Wiscasset Bay Gallery, which is just 100 metres away. Suitable for 2 guests, the Wiscasset holiday home offers hiking, mini golf, and cycling to diversify guests' leisure.
South Portland Vacation Rentals Oceanfront
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Best-rated
Island View House Bnb Self Check-In
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
Island View House Bnb Self Check-In Portland is located 2.6 km from the 47.5-acre public Edward Payson Park and a 17-minute walk from Eastern Promenade. Wi-Fi is available for guests' business or leisure needs.
Island View House Bnb Self Check-In
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
Island View House Bnb Self Check-In
Island View House Bnb Self Check-In Portland is located 2.6 km from the 47.5-acre public Edward Payson Park and a 17-minute walk from Eastern Promenade. Wi-Fi is available for guests' business or leisure needs.
Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
Nestled 4.7 km from McFarland Island, the 1-bedroom Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa is boasting a patio and a golf course for guests' enjoyment. Suitable for up to 4 guests, the holiday home offers opportunities for canyoning, snow skiing, and cycling.
Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Garden area
Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views
Nestled 4.7 km from McFarland Island, the 1-bedroom Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views Boothbay Harbor villa is boasting a patio and a golf course for guests' enjoyment. Suitable for up to 4 guests, the holiday home offers opportunities for canyoning, snow skiing, and cycling.
The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing
- Picnic area/ Tables
- Free parking
- Air conditioning
- Flat-screen TV
- Live entertainment
- Sun terrace
To enjoy your vacation in Portland, stay at the spacious 1-bedroom The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing Portland, which is 2.2 km from the well - respected Portland Museum of Art and around 20 minutes' walk from Casco Bay Islands. This 84 m² apartment is situated in proximity to the laid-back Munjoy Hill and offers a sun deck and a picnic area.
The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing
- Picnic area/ Tables
- Free parking
- Air conditioning
- Flat-screen TV
- Live entertainment
- Sun terrace
The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing
To enjoy your vacation in Portland, stay at the spacious 1-bedroom The Brew House - 2Nd Floor Private Apartment - Located Above Newscapes Brewing Portland, which is 2.2 km from the well - respected Portland Museum of Art and around 20 minutes' walk from Casco Bay Islands. This 84 m² apartment is situated in proximity to the laid-back Munjoy Hill and offers a sun deck and a picnic area.
South Portland Vacation Rentals with Private Pool
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Private beach
All Points' End
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Located just around the corner from Sebago Cove, the 3-bedroom All Points' End Naples villa gives easy access to various tourist attractions in the area. The Naples chalet is suitable for up to 4 guests and features private car parking.
All Points' End
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
All Points' End
Located just around the corner from Sebago Cove, the 3-bedroom All Points' End Naples villa gives easy access to various tourist attractions in the area. The Naples chalet is suitable for up to 4 guests and features private car parking.
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Beach access
Sea Shell
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Golf course
The 1-bedroom Sea Shell Villa Old Orchard Beach is situated approximately 5 minutes' walk from Congregation Beth Israel Orthodox Synagogue, featuring such comforts as Wi-Fi and parking.
Sea Shell
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Golf course
Sea Shell
The 1-bedroom Sea Shell Villa Old Orchard Beach is situated approximately 5 minutes' walk from Congregation Beth Israel Orthodox Synagogue, featuring such comforts as Wi-Fi and parking.
Hasty House Studio
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
The 1-bedroom Hasty House Studio Auburn boasts a convenient location around 700 metres from Veteran's Park. The maximum occupancy at the 23 m² apartment is 2 guests.
Hasty House Studio
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Hasty House Studio
The 1-bedroom Hasty House Studio Auburn boasts a convenient location around 700 metres from Veteran's Park. The maximum occupancy at the 23 m² apartment is 2 guests.
Cabin At The Beach
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
Up to 6 guests can stay at the 2-bedroom Cabin At The Beach Old Orchard Beach and enjoy the miniature Pirate's Cove Golf Course, located approximately 5 minutes' walk away. This 1-bathroom villa features opportunities for cycling and fisheries in the area, 4.4 km from Monkey Trunks Saco.
Cabin At The Beach
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
Cabin At The Beach
Up to 6 guests can stay at the 2-bedroom Cabin At The Beach Old Orchard Beach and enjoy the miniature Pirate's Cove Golf Course, located approximately 5 minutes' walk away. This 1-bathroom villa features opportunities for cycling and fisheries in the area, 4.4 km from Monkey Trunks Saco.
Are you in a hurry?
Here is a quick list of Vacation Rentals in South Portland, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| The Coastal Connection |
7.0 / 10 (1 Reviews) |
From 670$ | |
| Hallowell Rooming House |
9.0 / 10 (312 Reviews) |
From 110$ | |
| Lovely Studio W/Full Kitchen/Free Wifi- Next To River/Antique Shops/Restaurants |
9.3 / 10 (20 Reviews) |
From 49$ | |
| Island View House Bnb Self Check-In |
9.2 / 10 (162 Reviews) |
From 334$ | |
| Brand New Guest Apartment With Furnished Deck, Fast Wifi, Dock, & Water Views |
9.3 / 10 (29 Reviews) |
From 117$ |
Frequently Asked Questions
Which vacation rentals in South Portland are closest to the beach?
The Cabin at the Beach and Walk to Willard Beach offer quick walks to the sandy shore. Enjoy the local beach amenities and beautiful sunsets.
Visit early in the morning for beach access before crowds arrive and enjoy a peaceful morning.
Are there vacation rentals in South Portland with water views?
The Brand New Guest Apartment offers stunning water views and a furnished deck. Enjoy the beautiful scenery while relaxing at your rental.
Book your stay during weekdays to find better rates for waterfront rentals.
What vacation rentals are pet-friendly in South Portland?
The Hasty House Studio welcomes pets, making it a great choice for those traveling with dogs. Enjoy spending time together in a cozy setting.
Check for specific pet policies and fees to avoid surprises during your stay.
Which vacation rentals in South Portland have a full kitchen?
Lovely Studio W/Full Kitchen and The Brew House - 2Nd Floor Private Apartment both feature full kitchens. Prepare meals easily during your stay.
Shop at local markets like the Portland Farmers' Market for fresh ingredients to use in your kitchen.
Are there budget-friendly vacation rentals in South Portland?
The Lovely Studio and All Points' End provide affordable options for travelers. Both options maintain comfort without breaking the bank.
Book in advance during off-peak seasons, like early spring, to secure lower rates.
What vacation rentals in South Portland have two bedrooms?
Consider The Coastal Connection or Forest City Oasis And Spa for spacious two-bedroom options. Ideal for families or larger groups.
Look for last-minute deals to find budget-friendly two-bedroom rentals.
Which vacation rentals in South Portland are great for families?
Sunny House, By The Beach and Modern Getaway By The Sea are excellent choices for families. Both offer space and comfort near beach activities.
Choose a rental with a backyard for kids to play safely when not at the beach.
What is a popular local festival to attend in South Portland?
The South Portland Arts & Crafts Festival in September showcases local artisans and crafts. It is a great way to experience local culture.
Arrive early on festival days to find convenient parking and explore before it gets crowded.
How can I get around South Portland easily?
Use local bus services like the South Portland Bus Lines for convenient transport. They connect major areas, including downtown and beaches.
Purchase a day pass for buses to save on travel costs when exploring multiple locations in a day.
What are some must-try local foods in South Portland?
Enjoy fresh seafood dishes like lobster rolls at local restaurants. Places like the Lobster Shack are well-known for their quality.
Visit local food trucks during lunch hours for quick and delicious meals under $10.