Family-friendly holiday rentals in Cumberland County

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

Cozy Tiny Home | Fireplace • 9 Miles to Portland

This unique cottage has a style all its own. Discover modern comfort in our brand-new suburban tiny home located in The Downs in Scarborough, ME! This stylish space offers all-new amenities and a cozy atmosphere. Ideal for solo travelers or couples, but can accommodate up to four guests. Enjoy a private escape while being ~9 miles from Portland and ~6 miles from the beach. Experience efficient living without compromising on luxury. Book now for a fresh, contemporary getaway!

Cozy Maine Barn Hideaway- 2nd Floor Guesthouse

Welcome to our spacious 1000 sq. ft. Maine barn guesthouse! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

The Barnhouse with hot tub

Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

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.

Glorious Getaway on the Eastern Promenade

This first-floor apartment is just steps from beautiful Casco Bay! On a quiet residential street, there is plenty of on-street parking available. There are several wonderful restaurants and cafes right in the neighborhood within walking distance, along with many local breweries, distilleries, and shopping spots. The historical Old Port and Downtown Portland are a fifteen-minute walk or a quick Uber, so park your car and forget about it for a while!

Downtown Historical Victorian 2 BR APT

The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Oceanside Modern Victorian 2BR- East End/ Downtown

Classic New England style home, recently renovated and updated with modern amenities. A stone's throw from Portland's best public park, The Eastern Promenade. The Promenade boasts beautiful ocean views, a public beach, basketball & tennis courts & large playground. The neighborhood offers great restaurants and coffee shops. The Old Port and the rest of Downtown Portland is a 10 minute walk or 4 minute Uber ride away.

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Cozy 2 BR Apt in Walking Distance to Restaurants

This is a private two bedroom apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.