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Best Vacation rentals and Airbnb offers in South Portland, ME
9.7 138 reviews
South Portland, ME
08/22 – 09/05
$267/nighttotal: $3738 (14 )
Cape Elizabeth Furnished Private In-law Apartment
1 2
apartment , Cape Elizabeth
This Cape Elizabeth apartment is conveniently located near downtown Portland, beaches, walking and biking trails, and the airport, making it an ideal base for exploring the area. The apartment has consistently received excellent ratings for location, cleanliness, and overall experience. The apartment is a one-bedroom unit with one bathroom, comfortably accommodating up to two guests. Amenities include a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and high-speed internet, ensuring a comfortable and enjoyable stay.
10 45 reviews
South Portland, ME
08/21 – 08/24
$564/nighttotal: $1692 (3 )
Brand New 1 Bedroom Apartment In Portland
1 4
apartment , Portland
This newly remodeled 1-bedroom apartment is located in Portland's historic West End, offering city center access and proximity to Bayside Bowl, Casco Bay Lines Ferry Terminal, Center for Cultural Exchange, Southworth Planetarium, Portland Observatory, and Maine Narrow Gauge Railroad. This accommodation features a fully equipped kitchen with a fridge, microwave, and dishwasher, complimentary WiFi, air conditioning, an in-unit washer/dryer, and off-street parking available a short 2-3 minute walk away, accommodating up to 4 guests.
10 7 reviews
South Portland, ME
08/14 – 08/16
$280/nighttotal: $560 (2 )
Stylish Westbrook Studio, 10 Min To Portland
1 2
apartment , Westbrook
This newly renovated studio apartment is located in Westbrook, just minutes from downtown Portland. This hotel-like studio offers a full kitchen, air conditioning, free parking, and a capacity for 2 guests, with a modern bathroom and a dedicated workspace.
9.8 351 reviews
South Portland, ME
08/14 – 08/16
$618/nighttotal: $1236 (2 )
🌟🌟🌟🌟🌟 Cute, Clean, Quaint West End
3 2
apartment , Portland
This Portland apartment is located in the West End, a short walk from Casco Bay, the Old Port, and major transportation hubs. It has received excellent ratings for cleanliness, location, and user experience. The apartment has three bedrooms and one bathroom, comfortably accommodating up to eight guests. It features a simple kitchen, air conditioning, parking, and entertainment options like Hulu and Netflix.
South Portland, ME
06/27 – 06/28
$1355/nightfor 1 night
King Bed Studio Suite With Laundry & Gym Access
1 2
studio , Portland
This modern studio apartment is situated in a Portland district, offering easy access to the city's attractions. This accommodation features a king bed, a full kitchen, in-unit laundry, complimentary WiFi, and on-site parking for $40 per night, with a 21+ booking policy.
9.7 84 reviews
South Portland, ME
08/22 – 09/05
$234/nighttotal: $3276 (14 )
Spacious, Quiet And Easy Walk To Downtown.
1 2
apartment , Portland
This first-floor apartment is located in a friendly Portland neighborhood, within walking distance of downtown Portland and directly across from a park. The 1-bedroom unit features a railroad-style layout, sleeps 2 guests, includes a full kitchen with dishwasher, in-unit laundry, and a clawfoot tub, offering easy access to downtown attractions and nearby green space.
9.9 300 reviews
South Portland, ME
10/21 – 10/31
$333/nighttotal: $3330 (10 )
Charming Modern West End Gem
2 3
apartment , Portland
This West End Portland apartment rental is located on a quiet residential street, approximately one mile from downtown Portland and walking distance to local shops and restaurants. The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a private garden, and designated parking.
9.7 286 reviews
South Portland, ME
08/22 – 09/05
$277/nighttotal: $3878 (14 )
Open Concept Loft In The Heart Of Downtown Center
1 2
apartment , Portland
This downtown Portland apartment, located in a historic 1890s building, offers easy walkability to numerous attractions. The one-bedroom unit sleeps four with a sofa bed, features a fully equipped kitchen, private back deck, and shared laundry facilities; guests can explore nearby dining and activities listed in the provided guide.
9.8 41 reviews
South Portland, ME
08/21 – 08/24
$443/nighttotal: $1329 (3 )
Staycation Here! Fast Wi-fi.
1 4
apartment , Portland
This top-floor Portland apartment, in a four-unit building across from a park, offers complete privacy and easy access via multiple entrances. The 2-bedroom, 1-bathroom unit sleeps 4, features a full eat-in kitchen with modern appliances (fridge, freezer, microwave, dishwasher), fast WiFi, air conditioning, and a large porch with park views; quiet hours are enforced.
9.5 93 reviews
South Portland, ME
06/27 – 06/28
$413/nightfor 1 night
Cozy Back Cove Apartment - 5 Min From Old Port
1 2
apartment , Portland
This Portland apartment rental, registration #STHR-005198-2023, is conveniently located near Back Cove, offering scenic views of the Portland skyline and easy access to the Old Port's restaurants and shops. The spacious one-bedroom unit, sleeping up to two guests, features air conditioning, parking, and a kitchen with a refrigerator; a nearby coffee and smoothie bar provides convenient morning options.
9.7 6 reviews
South Portland, ME
06/27 – 06/28
$664/nightfor 1 night
Sunny Zen West End Apt
1 2
apartment , Portland
This Portland apartment rental is conveniently located a 10-minute walk from Maine Medical Center, the Western Promenade, and Deering Oaks Park, offering easy access to restaurants and shops. The spacious first-floor unit features a newly renovated kitchen and living area, sleeps two guests, includes private outdoor seating, and offers a quiet, peaceful atmosphere with occasional shared-space access to an adjacent bedroom.
10 18 reviews
South Portland, ME
08/21 – 08/24
$666/nighttotal: $1998 (3 )
Beach Lovers' Dreamhouse
1 4
apartment , South Portland
This South Portland home, a short walk from Willard Beach and Casco Bay, offers easy access to restaurants, shops, and a bakery. The two-bedroom, two-bathroom house sleeps four, features a full kitchen with dishwasher, a private backyard with cornhole, and off-street parking for two cars.
Best South Portland, ME vacation rentals with a balcony
10 2 reviews
South Portland, ME
10/21 – 10/31
$4299/nighttotal: $42990 (10 )
Charming Historic Estate | Perfect For Wedding Headquarters, Groups & Events
10 3
apartment , Portland
This exquisitely restored 1800 Thomas Delano house, located in Portland's West End, offers easy walking access to the Arts District and Old Port. The 4,790-square-foot property boasts 11 bedrooms, 5 bathrooms, and can accommodate up to 18 guests, featuring a private backyard with patio, grill, and seasonally available antique carriage house for private dining.
South Portland, ME
08/14 – 08/16
$1228/nighttotal: $2456 (2 )
Enjoy The Good Life. Free Parking, Ac In Bedroom.
1 2
apartment , Portland
This Portland apartment is located a 7-minute walk from the Portland Museum of Art and 0.9 miles from the Portland Downtown Historic District. This 4310 sq ft rental offers 1 bedroom, 1 bathroom, and can accommodate 2 guests, featuring air conditioning, a balcony, a garden, and a full kitchen with a dishwasher and microwave, plus complimentary WiFi and free parking.
South Portland, ME
10/21 – 10/31
$296/nighttotal: $2960 (10 )
2br W/ Parking | 5 Min To Downtown
2 3
apartment , Portland
This two-bedroom apartment is centrally located in Portland, a five-minute drive from downtown, within 0.3 miles of Back Bay and 0.2 miles of the University of Southern Maine, and a short drive to the Old Port. This pet-friendly dwelling accommodates up to six guests with a fully equipped kitchen, complimentary high-speed Wi-Fi, a private deck, and on-site and street parking.
South Portland, ME
08/14 – 08/16
$2018/nighttotal: $4036 (2 )
Cozy Home In Westbrook Close To Beaches And Portland.
2 2
apartment , Westbrook
This Westbrook apartment is located 10 minutes by car from Portland International Airport (PWM) and offers convenient access to attractions like the Tate House Museum and Neal S. Dow House. This 1700 sq ft residence accommodates up to 4 guests and features air conditioning, a kitchen with a fridge, microwave, and dishwasher, a swimming pool, spa, terrace, garden, and parking.
Our Favorite Family-Friendly Vacation Rentals in South Portland, ME
These family-friendly vacation rentals in South Portland, ME offer plenty of room to spread out near local beaches.
10 31 reviews
South Portland, ME
08/14 – 08/16
$1147/nighttotal: $2294 (2 )
Eastbayside/munjoy - Charming Downtown Escape
3 2
apartment , Portland
This East Bayside Portland condo is conveniently located within walking distance of the State Theatre and Cathedral of the Immaculate Conception, offering easy access to Portland's culinary and entertainment scene. This 1100-square-foot apartment features three bedrooms, two bathrooms, and accommodates up to six guests, boasting amenities such as a fully equipped kitchen, air conditioning, parking, and internet access.
9.9 565 reviews
South Portland, ME
10/21 – 10/31
$356/nighttotal: $3560 (10 )
Cozy East End 2 Bdrm. With Private Entrance
1 3
apartment , Portland
This 2-bedroom apartment is located on Munjoy Hill, just a short walk from Washington Avenue's restaurants and the Eastern Promenade's scenic views. The apartment has excellent user, location, and cleanliness ratings. The apartment can accommodate up to 4 guests and has a well-equipped kitchen, free parking, and keyless entry. You can enjoy the apartment's cozy atmosphere with books, games, and streaming services.
9.9 367 reviews
South Portland, ME
10/13 – 10/25
$230/nighttotal: $2760 (12 )
Explore Portland From A 18th-century Victorian
1 2
apartment , Portland
This top-floor Portland apartment, located steps from restaurants like the Knotted Apron and Woodfords Bar & Grill and a short distance from Portland's Old Port, offers easy access to public transportation and the Portland International Jetport. The unit features one bathroom, sleeps up to four guests (with an extra bedroom costing $50/night), includes a full kitchen with a dishwasher, and boasts Victorian-style décor with hardwood floors, a clawfoot tub, and two couches.
South Portland, ME
10/21 – 10/31
$457/nighttotal: $4570 (10 )
Forest City Oasis And Spa
2 3
apartment , South Portland
This 2-bedroom, 1-bathroom apartment in South Portland offers a tranquil garden oasis with a pond and waterfalls, located just a 5-minute drive from downtown Portland and its cultural attractions like the Maine Military Museum and Lyric Music Theater. Guests can enjoy luxurious indoor amenities including a fireplace and jacuzzi, outdoor living spaces with a sauna and fire pits, and convenient in-unit laundry, with opportunities for birdwatching, motor boating, and whale-watching nearby.
Frequently Asked Questions about vacation rentals in South Portland, ME
When is the best time to book a vacation rental in South Portland, ME?
The best time to book a vacation rental in South Portland is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and still enjoy pleasant weather.
What are the best Airbnb and vacation rentals in South Portland, ME?
What are the best restaurants with local dishes in South Portland, ME?
For classic New England fare, try The Lobster Shack. If you're looking for something a little more upscale, check out The Grill at the Portland Regency Hotel. For a more casual dining experience, try The Front Room, it's known for its delicious sandwiches and soups.
What are the most popular Airbnbs in South Portland, ME?
What are the best walking or cycling routes in South Portland, ME?
The Eastern Promenade is a great place for a walk or bike ride, it offers scenic views of the city and the harbor. The South Portland Greenway is a 5-mile paved trail that runs along the waterfront.
What are the best vacation rentals with a pool in South Portland, ME?
What are the benefits of choosing a vacation rental in South Portland, ME?
Vacation rentals in South Portland offer more space and privacy than a hotel room. You can also often find rentals that are pet-friendly or have amenities that are not available in hotels.
What are the best rentals or Airbnbs with a jacuzzi in South Portland, ME?
What are the top sports attractions and facilities in South Portland, ME?
The South Portland Community Center offers a variety of sports programs and facilities, including basketball courts, a swimming pool, and a fitness center. The city also has several parks with baseball fields, soccer fields, and tennis courts.
Destinations nearby
Best South Portland, ME vacation rentals with parking
9.9 951 reviews
South Portland, ME
06/27 – 06/28
$406/nightfor 1 night
Private Bungalow W/ Hot Tub, Free Parking & Pool
1 2
house , Portland
This charming bungalow is located in Portland, just a short walk from Thompson's Point, a lively entertainment and cultural hub, and a 20-minute drive to downtown Portland and Maine's beautiful beaches. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This cozy retreat features one bedroom and one bathroom, comfortably accommodating two guests. Enjoy a range of amenities including a private garden, a swimming pool, a jacuzzi, and a fully equipped kitchen, perfect for a relaxing and memorable getaway.
South Portland, ME
10/21 – 10/31
$158/nighttotal: $1580 (10 )
Charming Private 1st Floor Studio Apartment
1 3
studio , Portland
This studio apartment is located in Portland's Oakdale neighborhood, a short walk from Casco Bay and 9 minutes from Hadlock Field. This studio offers on-site parking, free Wi-Fi, a full kitchen with an oven and microwave, and a garden with a fire pit.
9.1 156 reviews
South Portland, ME
10/13 – 10/25
$294/nighttotal: $3528 (12 )
Island View House Bnb Self Check-in
1 2
apartment , Portland
This Portland apartment rental boasts an excellent location in the Downtown Historic District, within walking distance of the Portland Museum of Art, 0.8 miles from the Portland Downtown Historic District, and a short drive from Portland International Jetport and popular water parks like Funtown Splashtown USA. The unit includes a well-equipped kitchen with oven, microwave, and fridge, free Wi-Fi, free private parking, air conditioning, and a private bathroom; bed linens and towels are provided.
9.8 27 reviews
South Portland, ME
08/21 – 08/24
$853/nighttotal: $2559 (3 )
Gem On Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
2 4
apartment , Portland
This two-bedroom Portland condo, located in the Arts District, is a 10-15 minute walk from many attractions and shops, including Bayside Bowl and the Maine Sports Hall of Fame. The 2-bathroom apartment sleeps four guests, features a modern kitchen with a fridge, microwave, and dishwasher, 350 Mbps satellite WiFi, Smart TVs, free parking in a nearby garage, and a spa, perfect for exploring Portland's Old Orchard Beach Pier and Casco Bay Lines Ferry Terminal.
Browse Vacation Rentals with a Pool in South Portland, ME
Enhance your coastal getaway with a South Portland, ME vacation rental featuring a pool.
9.6 7 reviews
South Portland, ME
08/22 – 09/05
$5736/nighttotal: $80304 (14 )
Ocean Front Estate. 15 Min To Portland.
5 2
apartment , Scarborough
This ocean-front vacation home is located in Scarborough, within a 15-minute walk of Casco Bay and Higgins Beach, and 3 miles from Scarborough Beach State Park and Prouts Neck. The house enjoys an excellent user rating. This 10,000 square feet house has five bedrooms and can accommodate up to 10 guests. It features a kitchen with a refrigerator and an oven, a private pool, a fitness center, and an arcade/game room.
9.9 77 reviews
South Portland, ME
08/21 – 08/24
$495/nighttotal: $1485 (3 )
Tower Suite Plus: Hot Tub, W/d, Parking, Spa Bath
1 4
apartment , Portland
This charming apartment is located in a historic Victorian house in the West End of Portland, just a short walk from the Fore River Reservation trail system, Capisic Pond Park, and several restaurants. The apartment has received excellent ratings for cleanliness, location, and user experience. This spacious apartment comfortably sleeps four guests and includes two bedrooms, a newly renovated bathroom, and a lounge/kitchenette. Guests can enjoy a half-acre yard with picnic tables, a year-round hot tub, a seasonal swimming pool, and a Level 2 EV charging station.
South Portland, ME
10/13 – 10/25
$633/nighttotal: $7596 (12 )
Portland Pool House - Minutes To The Old Port!
3 2
house , Portland
This Portland vacation home is located a short distance from the Old Port, 2.7 miles from the Portland Observatory, and 3.2 miles from Merrill Auditorium. This 2150 sq ft, 2-bedroom, 2-bathroom rental accommodates up to 11 guests and features air conditioning, a kitchen, free WiFi, free private parking, and a private swimming pool with a terrace offering garden views.
10 17 reviews
South Portland, ME
10/13 – 10/25
$928/nighttotal: $11136 (12 )
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches And Downtown Portland
3 2
apartment , Scarborough
This Scarborough vacation rental, minutes from beaches, lighthouses, and Portland's Old Port, offers convenient access to Thompson's Point, Old Orchard Beach, the Old Orchard Beach Pier, Children's Museum & Theatre of Maine, and the Maine Narrow Gauge Railroad Company & Museum. This three-bedroom, one-bathroom home sleeps five and boasts a private, solar-powered spa with a 90°F indoor fitness pool and hot tub, a four-season sunroom, an outdoor sauna, a fire pit, and a full kitchen including a fridge, microwave, and dishwasher; additional amenities include air conditioning, a swimming pool, a garden, and parking.
Search Coastal Vacation Rentals near South Portland, ME
Discover charming seaside vacation rentals in South Portland, ME near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
9.7 30 reviews
South Portland, ME
08/22 – 09/05
$414/nighttotal: $5796 (14 )
Willard Beach Vacation Home 2 With Partial View!
1 2
apartment , South Portland
10 1 review
South Portland, ME
08/22 – 09/05
$542/nighttotal: $7588 (14 )
Modern Waterfront Apt With Bay Views
1 2
apartment , Falmouth
9.9 85 reviews
South Portland, ME
10/13 – 10/25
$183/nighttotal: $2196 (12 )
1bd/1ba In Knightville South Portland
1 2
apartment , South Portland
10 18 reviews
South Portland, ME
10/13 – 10/25
$373/nighttotal: $4476 (12 )
Updated Cottage - Steps To Pine Point Beach!
2 2
cottage , Scarborough
Top-Rated 5-Star Vacation Rentals in South Portland, ME
These high-end vacation rentals in South Portland, ME offer luxury living and unmatched quality near the shore.
9.9 147 reviews
South Portland, ME
10/13 – 10/25
$202/nighttotal: $2424 (12 )
Peaceful 1br | Reading Nook | Near Portland
1 2
apartment , Westbrook
Best Vacation Rentals with a Steam Room in South Portland, ME
Elevate your wellness routine with a vacation rental featuring a sauna in South Portland, ME , ideal for a restorative end to your day.
10 1 review
South Portland, ME
10/13 – 10/25
$723/nighttotal: $8676 (12 )
Sauna - Spacious And Centrally Located! Two Connected Apartments- Sleeps 11
