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Family-friendly vacation rentals in Cumberland County

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Top-rated family-friendly rentals in Cumberland County

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

Guest favorite
Apartment in Portland
"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.
Jan 18 – 25
$321 per night
4.97 out of 5 average rating, 212 reviews
Guest favorite
Apartment in Lisbon falls
Charming Victorian farmhouse 1880's bedrooms-2
Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.
Nov 17 – 24
$85 per night
4.95 out of 5 average rating, 375 reviews
Guest favorite
Home in Hollis
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.
Aug 19 – 24
$160 per night
4.98 out of 5 average rating, 349 reviews

Popular amenities for Cumberland County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Tiny home in Harrison
MILLION$ views, HOT TUB, Crooked RIVER, 14 acres
Aug 14 – 21
$460 per night
4.9 out of 5 average rating, 277 reviews
Guest favorite
Apartment in Topsham
Maine Stay with private hottub, near Brunswick
Jul 10 – 17
$152 per night
4.87 out of 5 average rating, 489 reviews
Guest favorite
Home in Portland
Peaceful Oasis with Water Views and Hot Tub!
Mar 9 – 16
$683 per night
4.96 out of 5 average rating, 180 reviews
Guest favorite
Apartment in Falmouth
Falmouth 3br near Town landing
Mar 31 – Apr 7
$311 per night
4.89 out of 5 average rating, 167 reviews
Guest favorite
Home in Old Orchard Beach
Luxury Beach House Old Orchard Beach Maine
Mar 25 – Apr 1
$856 per night
4.96 out of 5 average rating, 107 reviews
Superhost
Cottage in Harpswell
Beautiful Nezinscott Cottage on Bailey Island
Apr 25 – May 2
$900 per night
5.0 out of 5 average rating, 3 reviews
Guest favorite
Apartment in Old Orchard Beach
Surf Inn #1
Apr 2 – 9
$150 per night
4.78 out of 5 average rating, 18 reviews
Guest favorite
Home in Falmouth
Andy's Retreat-Heated pool, Hot Spring jacuzzi, AC
May 19 – 26
$549 per night
4.95 out of 5 average rating, 63 reviews
Home in Old Orchard Beach
Luxurious home with a Private indoor heated pool
Jun 7 – 14
$539 per night
4.63 out of 5 average rating, 110 reviews
Home in South Portland
*OCEAN VIEWS*150 yds to Beach*HOT TUB*8 min to DT*
Mar 20 – 27
$359 per night
4.92 out of 5 average rating, 13 reviews
Condo in Portland
▲ Spacious 5 Bedroom, 3.5 Bath, Parking, Deck! ▲
Mar 24 – 31
$393 per night
4.61 out of 5 average rating, 299 reviews
Cottage in Phippsburg
Norway Pines Oceanfront Cottages
Jan 23 – 30
$679 per night
5.0 out of 5 average rating, 26 reviews

Family- and pet-friendly home rentals

Guest favorite
Guest suite in Freeport
Freeport Village Sunny Studio
Jan 15 – 22
$131 per night
4.71 out of 5 average rating, 490 reviews
Guest favorite
Apartment in Harpswell
Sunny Apartment on the Ocean.
Nov 28 – Dec 5
$100 per night
4.83 out of 5 average rating, 239 reviews
Guest favorite
Home in Biddeford
Private, spacious, colorful, fun & unique space
Nov 15 – 22
$86 per night
4.97 out of 5 average rating, 377 reviews
Guest favorite
Farm stay in Scarborough
434 Acres and a Cabin
May 7 – 14
$131 per night
4.85 out of 5 average rating, 214 reviews
Guest favorite
Cottage in Gray
Sunset Haven - Little Sebago Lake
Dec 7 – 14
$225 per night
4.9 out of 5 average rating, 188 reviews
Guest favorite
Apartment in Falmouth
Falmouth Waterfront Carriage House Apt
Jun 21 – 28
$248 per night
4.96 out of 5 average rating, 137 reviews
Superhost
Apartment in Portland
Studio w/ Patio, Sauna & Onsite Massage
May 29 – Jun 5
$125 per night
4.78 out of 5 average rating, 296 reviews
Guest favorite
Apartment in Freeport
1000 sq. ft. 1BR+ Apt Close to Town & Nature
May 4 – 11
$96 per night
4.91 out of 5 average rating, 195 reviews
Guest favorite
Home in Portland
3 bedroom house in the heart of Portland
Oct 25 – Nov 1
$429 per night
4.98 out of 5 average rating, 305 reviews
Guest favorite
Cabin in Windham
Private Hilltop Cabin, Lakes and Trails Abound..
Jan 31 – Feb 7
$284 per night
4.91 out of 5 average rating, 193 reviews
Guest favorite
Condo in Portland
Back Cove - Sunny 2nd Floor Condo
May 8 – 15
$118 per night
4.85 out of 5 average rating, 323 reviews
Guest favorite
Guest suite in Brunswick
Art House Gallery guest suite
Sep 27 – Oct 4
$128 per night
4.93 out of 5 average rating, 307 reviews

Family-friendly home rentals with a pool

Guest favorite
Apartment in Brunswick
Charming Saltwater Farm apartment
Sep 12 – 19
$113 per night
4.99 out of 5 average rating, 194 reviews
Guest favorite
Home in Bridgton
Moose Pond Mountain Escape
May 28 – Jun 4
$167 per night
4.89 out of 5 average rating, 152 reviews
Guest favorite
Apartment in Falmouth
Poolside Suite-Gateway to Portland
Apr 5 – 12
$156 per night
4.96 out of 5 average rating, 85 reviews
Guest favorite
Chalet in Frye Island
Steps to Lake Sebago
Nov 21 – 28
$285 per night
5.0 out of 5 average rating, 8 reviews
Home in Harpswell
The Point, At The Edge Of The Ocean
Sep 7 – 14
$706 per night
5.0 out of 5 average rating, 7 reviews
Condo in Old Orchard Beach
Steps to the beach, Pool, 3rd Floor ocean view
Mar 26 – Apr 2
$265 per night
4.75 out of 5 average rating, 8 reviews
Cottage in Old Orchard Beach
OCEANFRONT 2BR COTTAGE #4 SLEEPS 6
Nov 20 – 27
$425 per night
4.59 out of 5 average rating, 81 reviews
Guest favorite
Condo in Old Orchard Beach
LUXURY OCEANFRONT CONDO Best Location on the beach
May 27 – Jun 3
$268 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Bridgton
Hidden Haven at Moose Pond, sleeps 10
Jul 27 – Aug 3
$270 per night
4.94 out of 5 average rating, 54 reviews
Condo in Old Orchard Beach
Great Vacation-2 BR Condo, Beach, Amenities, Fun!
Jan 6 – 13
$270 per night
4.83 out of 5 average rating, 30 reviews
Home in Bridgton
Spacious 4 Bedroom Home/Moose Pond
Feb 11 – 18
$250 per night
4.78 out of 5 average rating, 9 reviews
Townhouse in Saco
Make Summer Memories in Saco ME !
Jan 19 – 26
$430 per night
4.4 out of 5 average rating, 5 reviews

Destinations to explore