Family-friendly holiday rentals in Portland

5.0 out of 5 average rating, 107 reviews

An inviting entryway is presented under a large, sloping roof supported by exposed wooden beams. Comfortable seating is arranged on the porch, with decorative pumpkins placed on the ground. Pathways made of stones lead to the entrance, surrounded by a tranquil natural setting.

Cottage in Biddeford

Secluded Coastal Home & Cottage 3 Minutes to Beach

Escape to Thistle Pond Cottage, a peaceful coastal retreat in southern Maine. Nestled on 2 acres with pond views, lush gardens, and local wildlife, it’s minutes from beaches and Portland. Every stay begins with homemade bread from our kitchen and thoughtful, locally sourced welcome accompaniments. Weather and seasonal permitting, guests may occasionally savor a host-prepared wood-fired pizza made with fresh garden ingredients. Cozy, bright, and full of garden-to-table charm and seasonal delight.

Indoor spacesFamilyDecor

Home in Old Orchard Beach

The exterior of a modern oceanfront home is captured, showcasing a two-story structure with light gray siding and a charming front entrance. Lush landscaping and a paved driveway enhance the appeal. Panoramic views of the beach and ocean are visible in the background.

Unique and Stunning Beachfront property Greygoose

Brand new hot tub open all year long Stunning inside out, this spectacular oceanfront property offers bold panoramic views of the Saco Bay! Imagine enjoying the morning sunrise from your private Master Bedroom deck or gathering with family and friends on the oceanfront deck or by the fire pit in the private patio courtyard. Fondly known as the ''GreyGoose'', this lovely home was extensively renovated in 2012 with impeccable attention to maximizing ocean views, and creating spacious living areas.

Indoor spacesKitchenCondition

4.92 out of 5 average rating, 189 reviews

4.96 out of 5 average rating, 179 reviews

A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You 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, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

KitchenIndoor spacesValue

5.0 out of 5 average rating, 249 reviews

A modern beach house is positioned along a serene shoreline, featuring large windows that reflect the colorful sunset. The exterior showcases a blend of natural materials and white accents, with a deck that offers expansive ocean views. Rocky shores frame the property, enhancing the coastal setting.

Home in Saco

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.

Indoor spacesFamilyBarbecue

4.99 out of 5 average rating, 483 reviews

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

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.

FamilyKitchenWi-Fi

4.97 out of 5 average rating, 306 reviews

Cottage in Portland

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.

KitchenIndoor spacesValue

4.99 out of 5 average rating, 199 reviews

Treehouse in Pownal

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

KitchenFamilyCleanliness

A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.

5.0 out of 5 average rating, 116 reviews

Luxury Retreat In Back Cove | 10 Min to Downtown

Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Indoor spacesFamilyAccuracy

Apartment in Peaks Island

A bright hallway leads into the living space, featuring light wood flooring and white walls. A dining area is seen to the left with a small table and chair, while decorative elements, including potted plants and books, add character to the space.

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.

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 236 reviews

An open dining area features a round wooden table surrounded by blue chairs. A comfortable living room area is visible, with a gray sofa and art on the walls. Large windows allow natural light to brighten the space, enhancing the modern design.

4.99 out of 5 average rating, 157 reviews

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!

KitchenIndoor spacesNearby

Apartment in Downtown Portland

A modern lounge area is highlighted by large skylights, allowing abundant natural light to fill the space. A sleek, white sectional is complemented by colorful accent pillows and a patterned area rug. Exposed brick walls add an element of rustic charm, with scenic views of the harbor visible through the glass.

Old Port Penthouse Suite - Amazing Harbor Views

CO2024-01992 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.

Indoor spacesFamilyComfort

4.97 out of 5 average rating, 328 reviews

A bright living room is presented with two white sofas and a light blue area rug. A glass coffee table sits at the center, accented by a small potted orchid. Natural light streams in through large windows covered by light curtains, enhancing the serene ambiance.

4.93 out of 5 average rating, 655 reviews

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!

Indoor spacesFamilyLaundry

Popular amenities for Portland family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 125 reviews

The modern cabin features a sleek design surrounded by lush greenery. Soft bistro lights create a warm glow, illuminating the outdoor seating area with two Adirondack chairs. The deck can be seen in the background, enhancing the inviting atmosphere of the natural setting.

Cabin in Freeport

Romantic hideaway cabin w/ access to spa - 26

KitchenIndoor spacesValue

Guest suite in South Portland

A patio area features white Adirondack chairs facing a scenic view of the water. Colorful flowers in various pots add vibrancy to the space, while an American flag gently flutters in the breeze. The tranquil waterway is visible beyond the floral arrangement.

Oceanfront with amazing views and private entrance

KitchenFamilyBathroom

4.99 out of 5 average rating, 907 reviews

4.9 out of 5 average rating, 331 reviews

A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.

Home in Falmouth

Amazing Bay View Home with Hot Tub

KitchenIndoor spacesSleep quality

4.96 out of 5 average rating, 229 reviews

An aerial view captures the modern cabin surrounded by lush greenery, featuring warm string lights illuminating the outdoor area. A hot tub is positioned near a cozy seating arrangement, with a gravel path visible leading away from the cabin.

Cabin in Kennebunk

HotTub+Firepit/5 min to DockSquare, Dining, Beach

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 137 reviews

The lodge-style home stands amid tall trees, showcasing a modern dark exterior. A gravel driveway leads to the house, which features a welcoming front entrance. The surrounding landscape is dotted with seasonal foliage, providing a serene setting.

Home in Standish

Beautiful Home w-Hot Tub & Pond access

KitchenIndoor spacesLocation

4.93 out of 5 average rating, 147 reviews

The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.

Guest suite in Portland

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

FamilyKitchenTV

4.91 out of 5 average rating, 148 reviews

Bus in Durham

Solar Powered Bus in Forest | Hot Tub + Wellness

KitchenFamilyDecor

4.98 out of 5 average rating, 200 reviews

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

Indoor spacesKitchenSleep quality

Family- and pet-friendly home rentals

Apartment in Cape Elizabeth

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.

Crescent Beach Gardens

KitchenFamilyParks

4.99 out of 5 average rating, 142 reviews

4.98 out of 5 average rating, 157 reviews

Home in Georgetown

Cottage on Todd Bay

Indoor spacesKitchenWalkability

4.94 out of 5 average rating, 193 reviews

An inviting living area features a comfortable sofa facing a large television mounted on the wall. A rustic trunk serves as a coffee table on a patterned area rug. Natural light enters through double doors with sheer curtains, adding warmth to the space.

Home in Portland

East End Unit

FamilyKitchenCleanliness

5.0 out of 5 average rating, 115 reviews

An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.

Home in Higgins Beach

Higgins Beach *New* Beach Home & Private Offices

Indoor spacesFamilyAccuracy

4.92 out of 5 average rating, 305 reviews

A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.

Home in Portland

Top Deck - Portland Property with Views!

FamilyKitchenCheck-in

4.99 out of 5 average rating, 237 reviews

A cozy living area is viewed through large glass sliding doors. A wooden coffee table is placed in front of a dark seating area, complemented by two plush pillows. A colorful piece of wall art adds vibrancy to the light-toned walls, enhanced by natural light from the outdoors.

Cabin in Georgetown

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

KitchenIndoor spacesWalkability

4.96 out of 5 average rating, 263 reviews

A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.

Chalet in Standish

Blueberry Hill

Indoor spacesFamilyDecor

4.89 out of 5 average rating, 114 reviews

A bright living area features a wooden floor and a cozy, gray sofa. A blue writing desk is positioned beside a window, adorned with decorative bookshelves and plants. A vintage-style wood stove is set against a brick wall, with warm light enhancing the inviting atmosphere.

Home in Freeport

Charming Historic Freeport House

Indoor spacesFamilyNearby

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 525 reviews

Apt in Victorian Mansion w/ Hot Tub & Parking

KitchenFamilyAccuracy

Apartment in Cape Elizabeth

A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.

Portland & Beach & Lighthouses! Romantic! Lovely

KitchenIndoor spacesEV charging

4.88 out of 5 average rating, 616 reviews

5.0 out of 5 average rating, 107 reviews

Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

Indoor spacesFamilyView

5.0 out of 5 average rating, 105 reviews

A heated pool is set within a stone patio, surrounded by lush greenery. Two lounge chairs are positioned nearby, while modern heating units stand along the patio's edge. The pool's clear water reflects the surrounding area, offering a serene outdoor retreat.

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

KitchenFamilyBarbecue

4.98 out of 5 average rating, 124 reviews

A refreshing pool area is surrounded by well-kept landscaping and seating options. Two blue umbrellas provide shade over metal chairs and tables. Colorful pool floats are positioned in the clear water, and a charming white structure is visible in the background.

Apartment in Falmouth

Poolside Suite-Gateway to Portland

FamilyKitchenAmenities

4.99 out of 5 average rating, 249 reviews

A charming exterior of the historic residence showcases a well-maintained garden filled with vibrant purple flowers and greenery. The pale yellow siding of the house complements the octagonal window and green door, offering a welcoming appearance.

Apartment in Brunswick

Charming Saltwater Farm apartment

KitchenFamilyCheckout

4.98 out of 5 average rating, 292 reviews

Maine Hacienda w/hot tub & seasonal pool

FamilyIndoor spacesLayout