
Family-friendly holiday rentals in Portland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Portland
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Quiet Comfy Victorian Escape
Spend your vacation, work-trip, or weekend getaway in this lovely renovated cozy 2 bedroom unit. Apartment 2 is located on the second floor of a three family house where you have access to all the modern appliances: refrigerator, W/D, microwave and TV in the living room. A brand new queen bed each bedroom, with seat in cozy seating in the living room. Located in the very central Oakdale neighborhood, this unit is steps from Deering Park, Sea Dogs stadium, USM Law School and Portland's Old Port.

PRlVATE SUlTE in the Heart of East End Portland
Private Suite in the Heart of East End Portland. Sunny, elegant, Victorian studio with private entrance, bathroom and mini-kitchen area. This location is walkable to award winning restaurants, excellent cafes, the East End Beach where you can rent kayaks, ferries to the islands and more! A perfect romantic getaway close to anything you want to come to Portland to see and do, yet in the quiet, tree lined neighborhood of Munjoy Hill and the scenic East End. See guidebook included in this listing:)

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

4br2ba House+parking@PeacefulOasis on Munjoy Hill
This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Curated 2BR East End Retreat-Walk to Beach +Dining
Prime Munjoy Hill spot near ocean! A quick and easy walk to the Eastern Promenade park, East End Beach, and restaurants, cafes, food trucks, and breweries. Yet, our immediate vicinity is peaceful and quiet. It’s the best of both worlds. Whether you’re here to relax by the water or enjoy the local food scene, this location has it all. Only a 5 minute drive to the Old Port- or take the 30 min walk on the scenic East End trail along the water (20 min walk via the direct route).

Private Garden Retreat on Munjoy Hill
This well-appointed, new space is located on first floor of a modern, new home on Munjoy Hill - Portland’s most charming neighborhood. This convenient suite has a separate, private entrance with a private outdoor seating area. The location is perfect for walking - just minutes to excellent restaurants, coffee shops, gourmet market, Eastern Promenade, St. Lawrence Arts Center and Washington Avenue. Portland’s Old Port and bustling harbor is just a 10 - 15 minute walk down the Hill.

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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.

Modern & Sunny East End House. Private Parking!
This modern single-family home is just steps away from Portland's Eastern Promenade with its glorious views of Casco Bay and the islands. Many of the city's best restaurants, cafes, breweries & distilleries are all within a few blocks from the house. Park your car in the private parking spot behind the house and forget about it for a while and enjoy the city!

Crescent Beach Gardens
Simply spectacular - panoramic ocean, beach and island views from this spacious second story apartment with shady balcony surrounded by flowers, birds and the sounds of the sea. Fifteen minutes to Portland and every beach and lighthouse in the area. Short walk through the park to the beaches and ledges of three state parks.
Popular amenities for Portland family-friendly rentals
Family-friendly home rentals with a hot tub

Tiny house in the Birch Grove with private HOT TUB

Beautiful West End studio, hot tub, free parking

Luxury Year-round Treehouse with private hot tub

Cozy Rock Cabin #thewaylifeshouldbe

NewBuilt/HotTub/Great Location-4 min Kennebunkport

Maine Hacienda w/hot tub & seasonal pool

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool

Tiny house near the beach!
Family- and pet-friendly home rentals

The Chickadee Tiny House

Studio Apartment in Freeport

East End Unit

Entire house w/king bed, pet friendly & parking!

Portland 1 Bedroom Condo in the Arts District.

Simple Boothbay Log Cabin on Water

Writers Cabin in the Woods with Sauna!

Secluded Victorian Condo Downtown, Walk Everywhere
Family-friendly home rentals with a pool

Faith Lane with community pool

Ski Condo on Cranmore Mountain-Pool and Hot tub!

Poolside Suite-Gateway to Portland

There's No Place Like Home

Historic Schoolhouse c1866 Winter & Summer Dates

Steep Falls Escape, river & falls just steps away

Cozy Cottage with Ocean Views, Wells Maine

Loft Apartment on Tree-Lined Street in Falmouth
When is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £149 | £148 | £159 | £172 | £214 | £259 | £296 | £297 | £248 | £240 | £180 | £172 |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Quick stats about holiday rentals that are family-friendly in Portland

Total holiday rentals
Explore 820 holiday rentals in Portland

Nightly prices starting at
Portland holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 77,480 verified reviews to help you choose

Pet-friendly holiday rentals
Find 330 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
460 properties have a dedicated workspace

Wifi availability
820 of Portland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Portland rentals

4.9 Average rating
Portland stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
Portland’s top spots include Peaks Island, Portland Museum of Art and Crescent Beach State Park
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- Family-friendly rentals Cumberland County
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Scarborough Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- Pemaquid Point Lighthouse
- East End Beach
- Short Sands Beach
- King Pine Ski Area
- Cape Neddick Beach
- Gooch's Beach
- Cranmore Mountain Resort
- Coastal Maine Botanical Gardens
- Footbridge Beach
- Crescent Beach State Park
- Funtown Splashtown USA
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Conway Scenic Railroad
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