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.

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Top guest favourite
A bright bedroom features a spacious bed dressed in a floral quilt with decorative pillows. Large windows are adorned with sheer curtains, allowing natural light to fill the room. Two bedside tables with lamps complement the cozy atmosphere.
Flat in Oakdale
4.97 out of 5 average rating, 203 reviews

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.

Top guest favourite
A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.
Home in North Deering
4.96 out of 5 average rating, 154 reviews

"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

Top guest favourite
A bright dining area is illuminated by natural light streaming through a skylight. A wooden table is surrounded by dark chairs, while details such as a hat and a garment hang on the wall. A door leads to the serene outdoor view.
Home in Georgetown
4.99 out of 5 average rating, 111 reviews

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.

Top guest favourite
The spacious dining area features a black and white checkered floor, complemented by red walls. A rustic wooden table with four black chairs is placed centrally, while a vintage mirror reflects the room. Natural light filters through windows adorned with floral curtains, enhancing the cozy atmosphere.
Flat in East End
4.96 out of 5 average rating, 532 reviews

RETRO BnB in the Heart of East End Portland

Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!

Top guest favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 451 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Guest favourite
The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.
Home in Naples
4.98 out of 5 average rating, 176 reviews

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!

Top guest favourite
The kitchen features modern stainless steel appliances, including a range and microwave. Granite countertops provide ample workspace, along with white cabinets for storage. A coffee maker and various utensils are neatly arranged, contributing to a functional and well-equipped cooking area.
Apartment in Downtown Portland
4.88 out of 5 average rating, 490 reviews

Renovated Exchange St. Loft w/Free Parking

This renovated loft-style condo is right in the heart of the Old Port. Located on Portland's bustling Exchange Street, the loft is central to everything the Peninsula has to offer. Elevator access will take you from the apartment to the secure lobby. From there, shops, restaurants, night life and the working waterfront are just steps outside the door. Free off street parking is available for one car a few blocks away or a convenient pay-to-park garage is located next to the building.

Top guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 116 reviews

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!

Top guest favourite
A spacious seating area features a modern white leather sectional sofa adorned with colorful accent pillows. Large skylights provide natural light and showcase views of the harbor and cityscape. Exposed brick walls contrast with the smooth wooden floors, creating a cozy, yet contemporary environment.
Loft in Downtown Portland
4.97 out of 5 average rating, 298 reviews

Downtown Penthouse Suite - Stunning Harbor Views

CO2024-01992 Private 1850's Old Port Penthouse w/Breathtaking Views and Complimentary Parking Nearby. 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 ferries and smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Guest favourite
The entryway showcases a blend of modern and rustic elements, featuring a wooden accent wall and exposed brick. A low wooden bench and a round coffee table are positioned on a textured carpet, while a bank of mailboxes is mounted on one side, offering convenience for residents.
Apartment in Downtown Portland
4.86 out of 5 average rating, 379 reviews

Old Port on foot

Newly renovated, spacious and modern top-floor condo in a posh historic building in the heart of downtown Portland. Leave your car behind! Walking distance to tons of bars/restaurants, stores, a block from the Portland Harbor/Commercial St and 3 blocks from Merrill Auditorium. Please note there is an additional $50 cleaning charge for stays greater than 7 nights. For stays greater than 14 nights, the cleaning fee is $180.

Top guest favourite
A bright living room is illuminated by sunlight streaming through large windows. A round dining table with white chairs is set near a cozy seating area featuring a patterned sofa and decorative cushions. Built-in shelves display books and decorative items, complemented by warm wooden accents.
Flat in West End
4.94 out of 5 average rating, 599 reviews

Bright & Sunny West End Apartment.

This sunny 3rd-floor apartment is in a historic row house that was built in 1835. With the Portland Museum of Art and the State Theater a 5-minute walk away & the Old Port just 15, this home is steps from the best eateries, arts and shopping the city has to offer! When you arrive, park your car in your private spot behind the house and forget about it for a while.

Top guest favourite
A panoramic view of lush green land, featuring an array of colorful flowers. The coastline is visible in the distance, with water reflecting the clear blue sky. A shaded area with trees complements the vibrant plants, creating a serene outdoor environment.
Flat in Cape Elizabeth
4.99 out of 5 average rating, 111 reviews

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

When is the best time to visit Portland?

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Avg. price$257 SGD$256 SGD$275 SGD$296 SGD$371 SGD$447 SGD$511 SGD$512 SGD$429 SGD$414 SGD$311 SGD$298 SGD
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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 $64 SGD 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

Destinations to explore