
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.

Portland 2 Bed,2 Bath In The Heart of West End…
Modern & bright home in perfect location to explore all of Portland! Luxurious from top to bottom, inside and out. One off-street parking spot is provided. Wi-Fi and a 65” HD tv. No pets. Fully stocked kitchen has a gas stove, DW and water/ ice on fridge. 1 King Bed with new mattress! On-suite bath w/radiant floor heat. 2nd bed has a Queen Bed with new mattress and bedding. Bonus loft space for yoga, reading, Fenced in yard w/ patio furniture and a fire pit! Lic# STHR-004880-2022

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.

Oceanfront w/ Stunning views and Private Deck☀️🏖
Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Small cozy downtown loft
Cozy small private loft 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, Casco Bay bridge that connects Portland with South Portland, Cape Elizabeth, Scarborough, beaches and parks. Portland was named “City of the Year” in 2018 in Bon Appetit. Please note that bathroom/ shower are small. The apartment might not be suitable for tall individuals or elderly people due to steep stairs and slanted ceiling.

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!

Peaks Island Master Bedroom Suite
Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Sophisticated Charm at an unbeatable price!
Apartment is centrally located to all downtown amenities and transportation system. Located in the beautiful West End on a quiet residential street approximately 1 mile from the downtown area. Apartment (3rd floor) gets beautiful sun throughout and has all of the traditional charm and character of the West End homes but updated bathroom and kitchen, both recently remodeled in 2017. Rental includes access to one parking space for a small to mid size vehicle. STHR-001018-2019

Mary J. Eastburn House - Baxter Suite
City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.

Harborview - Curated East End Escape w/ Parking
Harborview is a newly renovated, top-floor apartment perched on the edge of Munjoy Hill in Portland's East End. This home is a short stroll to the Eastern Promenade and the East End Beach, the Casco Bay Islands Ferry Terminal, and the historic Old Port. The apartment features a spacious open kitchen, dining, and living room floor plan adjoined by a large private deck. It's the perfect spot to gather, relax, and dine while enjoying the breathtaking views of Casco Bay!

Central-Local Studio in Vibrant Portland, Maine!
Spacious and private studio apartment, with sitting area, queen size bed, table and chairs for dinning, kitchen and full bathroom. Newly updated appliances in a well maintained building. Wood floors lend charm, while modern decor makes for a contemporary feel. This comfortable space is perfect to come back to after exploring the surrounding neighborhood. The Studio is steps away from Portland's best restaurants, shops, nightlife and more!

Waterfront Two Master Suite Penthouse with Rooftop
CO2024-01785 Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

Sunset Suite 42
Breathtaking views, privacy, and convenient location make Sunset Suite a great place to be while visiting ME! The great room with a cathedral ceiling and skylights offers the best of natural light... day and night! The Portland skyline is all yours from your private and expansive deck as you put your feet up and reminisce about your day and plan for the next.
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

Luxury Home w/HOT TUB & Fire Pit

Resort-like 2 bed/1 bath - seasonal pool/hot tub

Romantic A-Frame cabin in the woods

LUX Designer Private Waterfront Hot Tub - Secluded

Beautiful West End studio, hot tub, free parking

HotTub/5min to K-port, Pet friendly, @anchorunwind

Amazing Bay View Home with Hot Tub
Family- and pet-friendly home rentals

The Chickadee Tiny House

Private Hill Top Apartment/w One Car Driveway

East End Unit

Crow's Nest

Private Guesthouse in the Woods

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Crescent Beach Gardens

Top of the Old Port-1 BR APT
Family-friendly home rentals with a pool

Faith Lane with community pool

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

Poolside Suite-Gateway to Portland

Historic Schoolhouse c1866 Winter & Summer Dates

Cozy Cottage with Ocean Views, Wells Maine

Loft Apartment on Tree-Lined Street in Falmouth

Maine Hacienda w/hot tub & seasonal pool

OOB Oasis: 5BR Home w/ Private Pool Near Beach
When is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £151 | £151 | £162 | £175 | £219 | £264 | £301 | £302 | £253 | £244 | £183 | £176 |
| 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 860 holiday rentals in Portland

Nightly prices starting at
Portland holiday rentals start at £38 per night before taxes and fees

Verified guest reviews
Over 77,360 verified reviews to help you choose

Pet-friendly holiday rentals
Find 310 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
490 properties have a dedicated workspace

Wifi availability
850 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
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Jersey City Holiday rentals
- Fitness-friendly rentals Portland
- Rentals with a patio Portland
- Cottage rentals Portland
- Rentals with a kayak Portland
- Waterfront rentals Portland
- Rentals with a firepit Portland
- Beach house rentals Portland
- Boutique hotels Portland
- Rentals with a hot tub Portland
- Beachfront rentals Portland
- Mansion rentals Portland
- Townhouse rentals Portland
- Hotel rooms Portland
- Pet-friendly rentals Portland
- Flat rentals Portland
- Rentals with a fireplace Portland
- Cabin rentals Portland
- Villa rentals Portland
- House rentals Portland
- Private suite rentals Portland
- Rentals with a washing machine and dryer Portland
- Rentals with an EV charger Portland
- Rentals with outdoor seating Portland
- Rentals with pools Portland
- Rentals with breakfast Portland
- Rentals with beach access Portland
- Rentals with a sauna Portland
- Apartment rentals Portland
- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Scarborough Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- York Harbor Beach
- Pemaquid Beach
- Cranmore Mountain Resort
- Willard Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Short Sands Beach
- Cape Neddick Beach
- East End Beach
- Gooch's Beach
- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Footbridge Beach
- Conway Scenic Railroad
- Things to do Portland
- Sports activities Portland
- Food and drink Portland
- Tours Portland
- Sightseeing Portland
- Art and culture Portland
- Things to do Cumberland County
- Sightseeing Cumberland County
- Sports activities Cumberland County
- Art and culture Cumberland County
- Food and drink Cumberland County
- Tours Cumberland County
- Nature and outdoors Cumberland County
- Things to do Maine
- Food and drink Maine
- Art and culture Maine
- Sports activities Maine
- Tours Maine
- Sightseeing Maine
- Nature and outdoors Maine
- Things to do United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Sightseeing United States
- Entertainment United States
- Food and drink United States
- Tours United States
- Nature and outdoors United States






