Family-friendly vacation rentals in South Portland

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Popular amenities for South Portland family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
Home in Portland
4.97 out of 5 average rating, 224 reviews

Stunning & Spacious 6BR Waterfront House + Hot Tub

PeterRating, 5 stars2 weeks ago
The house was perfect for our group of 12. It was spacious and well-cared for. While not located in downtown Portland, it was just minutes away by car. There was ample parking in the driveway and on the street. Meghan was a very responsive and flexible host. We had a great time.
Guest suite in Kennebunk
4.83 out of 5 average rating, 87 reviews

Cozy Studio with backyard hot tub!

DanielRating, 5 stars10 months ago
Great location in town that was walkable to some terrific dining spots on main street. Enjoyed the backyard BBQ and patio for a lovely dinner outside as well as peaceful morning coffee. Sherry was very helpful in recommending the studio space for us and available throughout our stay. Will highly consider this spot for future vacations in Kennebunk area.
Condo in Kennebunkport
4.93 out of 5 average rating, 27 reviews

Condo at the Resort at Goose Rocks

DeborahRating, 5 stars22 months ago
Meghan’s place was perfect for our family of four. A quick drive or bike to the beautiful beach; Woolf’s for fresh corn and pre-cooked lobster; Five Acre farm for freshly baked pies (love the honour pay system!). Also lots of amenities on the grounds to take advantage of (swimming, pool, tennis, pickle ball). Would happily stay at Meghan’s place again.
Superhost
Cottage in Wells
4.88 out of 5 average rating, 42 reviews

Beach Dreaming

ArtemRating, 5 stars8 months ago
A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.
Guest favorite
Apartment in Topsham
4.87 out of 5 average rating, 552 reviews

Cozy hot tub haven

ColeRating, 5 stars5 days ago
Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.
Superhost
Home in Harrison
4.9 out of 5 average rating, 308 reviews

Riverfront Luxury in the woods, Million $ Views.

KristieRating, 5 stars2 weeks ago
Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!
Guest favorite
Cabin in Rochester
4.94 out of 5 average rating, 230 reviews

awesome private cabin

JoshuaRating, 5 stars4 weeks ago
Dave was an amazing host and he provided the best possible get away for our first wedding anniversary. It was private there is so much beautiful outdoor art to look at and the hot tub was the perfect way to wind down after the day. If there was a 6 star option I would give it this was everything we wanted and needed and then some
Top guest favorite
Cottage in Wells
4.95 out of 5 average rating, 78 reviews

Beach Dreams Cottage - Wells, ME

CourtneyRating, 5 stars2 weeks ago
Cottage was exactly as expected and perfect for our little family get away! The porch really added to the space and the cieling fans were very impressive. We loved the quite area and friendly neighbors. Would definitely stay again.

Family- and pet-friendly home rentals

Guest favorite
Apartment in East End
4.87 out of 5 average rating, 1,036 reviews

Private Hill Top Apartment/w One Car Driveway

AmyRating, 5 stars1 week ago
This was a perfect stay for our 2 days in Portland. We could walk everywhere from the apartment. There were plenty of options for restaurants nearby.
Guest favorite
Apartment in Old Orchard Beach
4.93 out of 5 average rating, 200 reviews

The Upstairs Moose

ChristopherRating, 5 stars2 days ago
We arrived and saw either the hosts or prior renters had left a few key basic unopened items in the fridge to help ease us into our stay: items like half and half, some eggs and butter were present. The hosts had also made the effort to leave a small welcome and departing treat for me and the family that was a nice touch. The building was older but with that comes the charms of different features liked slightly raised floors at times and other anomalies. The rooms were freshly painted and we never saw any signs of pests inside.The location was close to the shore and walkable to the pier and attractions. The beach was extremely clean and though we only went at off hours (late night or sunrise) it was always relaxing. There is an active set of train tracks nearby so don't be alarmed, it's about a mile off I'd guess but you will hear them pass through.The roads were pretty quiet in the neighborhood and kids plays on the inactive street for hours. Thanks for the enjoyable stay, The Hornes
Guest favorite
Apartment in Lisbon falls
4.94 out of 5 average rating, 468 reviews

Charming Victorian farmhouse 1880's bedrooms-2

MollyRating, 5 stars2 days ago
Marcia’s place was exactly what we needed for the week. Convenient location in town with several walkable dining options. So happy we chose Marcia’s place for our vacation.
Guest favorite
Home in Bath
4.91 out of 5 average rating, 345 reviews

Gorgeous Studio on the Kennebec

AlexandraRating, 5 stars1 week ago
Easy 5 stars! Phillip was kind, proactive and responsive. The space, while quaint and simple, was clean, had all the essentials and, it was perfect for a week visiting my grandparents/ working remote! Not to mention my dogs loved being a half mile from the Bath dog park. Highly recommend if you’re looking for a Maine mid-coast getaway!
Top guest favorite
Home in Peaks Island
4.86 out of 5 average rating, 170 reviews

Booking Now: Year-Round Peaceful Island Getaway

CatherineRating, 5 stars2 weeks ago
Can’t say enough about how great our stay was! Andrew was incredibly responsive, let us check in early and check out late without even asking. It was a great location on the island, very walkable, even for my mother with a bad knee (she was exhausted after the first day though). Would absolutely stay again!! 10/10
Superhost
Apartment in East End
4.8 out of 5 average rating, 113 reviews

Come experience Portlandian life!

JoAnnRating, 5 stars9 months ago
Apartment was very good and has everything you need for your stay. Apartment was clean and easy access to downtown Portland with a 10 min walk. Joseph was very accessible we had a minor drain problem in bathroom and Joseph responded immediately and corrected the problem. Highly recommend this apartment for couples and small families. Would definitely rent in future. Thank you very much!!
Top guest favorite
Apartment in East End
4.97 out of 5 average rating, 464 reviews

Bright and cozy Munjoy Hill neighborhood apartment

KathleenRating, 5 stars2 weeks ago
This home was fabulous! The space was clean, lovely, and so comfortable. Additionally the neighborhood offered but walks in nature and restaurants/stores. I wish I could go back next month!
Superhost
Condo in Downtown Portland
4.77 out of 5 average rating, 690 reviews

Modern Condo, Victorian Charm. Walk To Everything!

SompurnaRating, 5 stars4 weeks ago
Super cute apartment in a great location and very responsive host! The apartment was clean and well stocked, and the Steve was very kind and responsive. He was also able to accommodate a very early check-in for us which was greatly appreciated. The location was great for getting around Portland. Our only complaint was that the free parking was not as easy/available as we had hoped, but the host did a great job compiling a list of other (paid) parking options. Overall loved it and highly recommend, just consider that you may have to pay for parking.

Family-friendly home rentals with a pool

Superhost
Cottage in Poland
4.61 out of 5 average rating, 18 reviews

Lake Beach House at Poland Spring Resort

Erin Rating, 5 stars10 months ago
Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!
Top guest favorite
Condo in Old Orchard Beach
5 out of 5 average rating, 15 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

JennyRating, 5 stars11 months ago
This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!
Guest favorite
Condo in Wells
4.85 out of 5 average rating, 187 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars2 weeks ago
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones
Cottage in Frye Island
5 out of 5 average rating, 10 reviews

Sebago Lake - A-frame cottage on Frye Island

TarynRating, 5 stars10 months ago
Perfect little spot on Frye Island! Great location, walking distance to our favorite beach on island as well as the general store. House was clean, comfortable, just as described. We enjoyed our stay!
Guest favorite
Apartment in Falmouth
4.97 out of 5 average rating, 94 reviews

Poolside Suite-Gateway to Portland

CameronRating, 5 stars4 weeks ago
Maryann is SUCH a treasure! She really is the hostess with the mostest! Gives great recommendations, homemade coffee and treats, and if you mention you like something, she might get it for you! Making this Philly girl a wannabe Maine resident! Couldn’t recommend more.
Guest favorite
Home in Portland
5 out of 5 average rating, 11 reviews

The Hill's on Buttonwood

DanielRating, 5 stars7 months ago
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown
Chalet in Frye Island
4.76 out of 5 average rating, 87 reviews

Cabin in Paradise

ChiaraRating, 5 stars9 months ago
My family and I had a awesome time enjoyed the quiet and relaxing days. Michael was very helpful and very quick responses to any questions we had.The cabin was very nice it felt like home was very comfortable slept very well. Everything about the cabin and the island was well worth going looking forward to going again in the future.
Condo in Old Orchard Beach
4.8 out of 5 average rating, 10 reviews

Steps to the beach, Pool, 3rd Floor ocean view

JessieRating, 5 stars10 months ago
We had a great time at Teri’s place. The condo was described exactly, clean and had everything that we needed. The beds and furniture were. very comfortable. The view from the balcony was beautiful with nice chairs set out to enjoy your coffee. It was a 30 second walk to the beach, which was great for having a Toddler. The pool and laundry was a plus. When we head back to OOB we would stay again.

Quick stats about vacation rentals that are family-friendly in South Portland

  • Total rentals

    260 properties

  • Total number of reviews

    20K reviews

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    250 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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