Family-friendly vacation rentals in South Portland

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Top-rated family-friendly rentals in South Portland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in South Portland

4.9 out of 5 average rating, 102 reviews

Cottage style home 2 blocks from the beach!

Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

Nov 15 – 22

R7,052 ZAR per night

Guest favorite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Love gardens, pine trees, campfires, and birds? Curious about tiny homes? Our 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping the beverage of your choice from your private deck. It will be a unique and amazing experience and one you will remember! Bonus: 2 super friendly dogs and a cat that will be around the property during your stay. New in 2024: A/C!!STHR-000718-2018

Sep 19 – 26

R2,882 ZAR per night

Guest favorite

Apartment in Portland

4.97 out of 5 average rating, 228 reviews

"Percival" Penthouse Suite - Amazing Harbor Views

2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Feb 26 – Mar 5

R6,986 ZAR per night

Guest favorite

Home in Gorham

4.99 out of 5 average rating, 138 reviews

Beautiful Home In Gorham Maine

Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

Jul 22 – 29

R3,313 ZAR per night

Guest favorite

Home in Hollis

4.98 out of 5 average rating, 360 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Oct 22 – 29

R3,445 ZAR per night

Superhost

Apartment in Portland

4.78 out of 5 average rating, 304 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

Sep 11 – 18

R2,084 ZAR per night

Guest favorite

Cottage in Portland

4.9 out of 5 average rating, 496 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet Portland neighborhood only a 7-10 minute drive (and $9 Uber ride) from downtown Portland, the Old Port, and all local visitor attractions. The cottage is a mile down the road from the Allagash Brewing complex and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Aug 17 – 24

R3,291 ZAR per night

Guest favorite

Apartment in Portland

4.97 out of 5 average rating, 354 reviews

Large Sunny Apartment Near Downtown/Arts District

Quiet neighborhood, quick walk to downtown Portland. Short drive to beautiful sandy beaches. Newly furnished *3RD FLOOR* apartment. Spacious rooms with mansard roof ceilings. Washer and dryer. Off street parking for one car. Clean and well maintained. We happily welcome guests, but if you or someone in your group has difficulty with stairs this *3rd floor* apartment may not be the best fit for you or your group.

Mar 30 – Apr 6

R3,516 ZAR per night

Guest favorite

Farm stay in Scarborough

4.85 out of 5 average rating, 214 reviews

434 Acres and a Cabin

Located 25 minutes from Portland and 10 minutes from the beach, the farm is a 434 acre agrarian escape. We grow cut flowers and organic produce We specialize in general farm goodness. Walk the miles of trails and experience a working cut flower farm in all seasons. Pets allowed. There is one double bed and a twin sized day bed with a pull out twin sized trundle underneath.

Mar 13 – 20

R2,843 ZAR per night

Guest favorite

Home in Biddeford

4.97 out of 5 average rating, 381 reviews

Private, spacious, colorful, fun & unique space

Large private comfortable annex with a SEPARATE entrance, bathroom and dining nook for our guests to enjoy in a farmhouse style family home built in 1850. Located on a quiet street 3 miles from Biddeford Pool Beach. 1 mile to the UNE Biddeford campus. 10 minutes to Saco train station. 15 minutes to Old Orchard Beach and 25 Minutes to the city of Portland and the Jetport.

Oct 29 – Nov 5

R1,858 ZAR per night

Guest favorite

Apartment in Portland

4.88 out of 5 average rating, 380 reviews

Updated stylish 1 BR Downtown Apt

Cozy small second floor 1 BD apt in a brick Victorian era home in Portland’s West End. The Old Port is only a 7 min walk away. The building is by Harbor View Memorial Park and Casco Bay bridge that connects Portland with South Portland, Cape Elizabeth, Scarborough, beaches and parks. Not to forget, Portland was named “City of the Year” in 2018 in Bon Appetit.

Jan 2 – 9

R2,880 ZAR per night

Guest favorite

Farm stay in Gray

4.94 out of 5 average rating, 249 reviews

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

Jan 23 – 30

R2,710 ZAR per night