Pet-friendly holiday rentals in Portland

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.

4.92 out of 5 average rating, 301 reviews

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10 – 12. Large yard. Off street parking 6-8. Portland License #STHR-002587-2020

PetsWalkabilityGetting around

4.95 out of 5 average rating, 110 reviews

Cabin in Freeport

A-frame w/ towering 18ft glass wall & deck - 15

The Escape is a gorgeous A-frame cabin that features an 18' wall of glass overlooking beautiful woods. It is set among the tranquil northern pines of the recently renovated campground on the edge of the famous dunes of the Desert of Maine. The cabin has everything you need to enjoy a luxurious, relaxing outdoor experience. It is just a short walk away from the Unwind Nordic Spa which includes a sauna, hot tub, plunge pool, cold plunge, and more. Disconnect from the world at this beautiful A-fram

WalkabilityPetsFamily

Apartment in Cape Elizabeth

A cozy living and dining area features comfortable seating, including a pair of light-colored armchairs and a round dining table. Soft lighting illuminates the space, and decorative accents, such as art and plants, create a welcoming atmosphere.

4.92 out of 5 average rating, 691 reviews

Portland + Cape Elizabeth + Beaches + luxurious!

Permit210780 •Luxurious 3 rm apt with 1322 5* reviews! Only a mi to the beach & 4.4 mi to Portlnd - Location! •1st flr Great Rm to dine & relax: microwave, fridge, toaster, Keurig, TV, cooktop •2nd flr huge bathrm & bedrm for 2 w/ another sitting rm + a 2nd bdrm w/ 1 Q & 2 twins •More than 2 people? Alter reservation #’s for additional cost •2 people wanting 2 bedrms? Only add a $50 cleaning fee for 2nd bdrm •luxurious furnishings & superior bedding! •I am known for thinking of EvErYtHiNg ;-l

Outdoor spacesWalkabilityBiking

4.91 out of 5 average rating, 596 reviews

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Outdoor spacesWalkabilityValue

The private roof deck features wooden flooring with a seating area that includes a small table and lounge chairs. Scenic views of the harbor and surrounding areas are visible, complemented by a clear blue sky above. A potted plant adds a touch of greenery.

4.96 out of 5 average rating, 537 reviews

Crow's Nest

Registration# 2018-4091. Watch the bustling harbor over coffee or wine on your private roof deck, walk to Portland's best restaurants, stroll the Eastern Promenade, shop your way to the heart of the Old Port...Just a taste of all that's within a short walk from the front door! You'll find more windows than walls in this airy sun-filled 'nest' in Portland's hippest neighborhood, the East End! NOTE: All guests must agree to House Rules below within 24 hrs of booking to be confirmed by host.

WalkabilityOutdoor spacesAccuracy

Superhost

A spacious dining area is highlighted by a wooden table surrounded by white chairs. A staircase with wooden railings leads to the upper level. Natural light fills the room through multiple windows, enhancing the warm wooden details of the walls and floor.

Loft in Portland

4.89 out of 5 average rating, 367 reviews

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

WalkabilityOutdoor spacesParking

Hotel room in Downtown Portland

A modern living area features a comfortable gray sofa draped with a soft throw. A wooden coffee table sits on a patterned rug, accompanied by a small black side table. A wall-mounted television is positioned against a light-colored wall, with large windows showcasing a view of brick buildings.

4.93 out of 5 average rating, 231 reviews

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

WalkabilityPetsFamily

4.98 out of 5 average rating, 192 reviews

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

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!

Outdoor spacesWalkabilityValue

5 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

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

PetsWalkabilityValue

A common area is depicted, featuring a spacious couch adorned with yellow pillows. A light wood coffee table is centered on a striped rug. Natural light flows through large windows, illuminating a dining table with several wooden chairs, complemented by a cozy décor.

4.97 out of 5 average rating, 515 reviews

Bright and cozy Munjoy Hill neighborhood apartment

Bright and cozy apartment in Portland's Munjoy Hill neighborhood with private backyard deck. Short walk (like a minute!) to neighborhood bagels, coffee, breweries, beach, playgrounds, restaurants and 15 minute walk to the Old Port & Downtown. Ample/free street parking available. Our family of four lives upstairs, our home is surrounded by flower gardens and located on the Portland Trail system. We welcome all folks of all backgrounds to our home and neighborhood!

Outdoor spacesPetsNearby

4.81 out of 5 average rating, 726 reviews

A spacious living area features comfortable seating, a dining table, and a fireplace. Natural light filters through large windows, highlighting the warm wood floors. The connected kitchen showcases modern appliances and a clean, airy layout, creating an inviting social space.

Apartment in West End

1875 West End Victorian | EV Charging + Parking

Step into a piece of Portland history in this private apartment inside an 1875 Victorian on quiet Pine Street in the heart of the West End. Original character meets modern comforts just a short walk from the Old Port, waterfront, and Maine Medical Center. Minutes away from great restaurants, coffee shops, museums and a 15-minute walk or a 5min taxi ride to the Old Port. An off-street parking spot is included. The apartment entry is entirely keyless and painless!

PetsWalkabilityNearby

A bright living area features a leather couch, a glass coffee table, and a comfortable chair. Natural light enters through bay windows adorned with plants. A large TV is positioned on a wooden stand, complementing the room's blend of modern and classic decor.

4.89 out of 5 average rating, 170 reviews

Back Cove Retreat | 3BR w/ Patio & 2-Car Parking

Historic charm meets modern comfort in Portland’s Back Cove. This renovated first-floor 3BR/2BA offers space, style, and parking for two cars — a rare Portland perk. Walk to the Back Cove trail, local coffee shops, restaurants, dog park, and sports fields. Or just a 5-minute drive to the Old Port and the bustling downtown waterfront area. The perfect home base for your Portland stay.

WalkabilityPetsQuiet

Popular amenities for Portland pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.85 out of 5 average rating, 229 reviews

A sunlit sunroom features three woven chairs adorned with soft cushions in varying shades of blue. A low wooden table with a vintage checkers board is situated in the center. Sheer white curtains gently drape around the windows, allowing natural light to enter.

Home in Falmouth

Beautiful +Nostalgic + Coastal Maine Cottage

Outdoor spacesPetsFamily

4.98 out of 5 average rating, 173 reviews

Home in West End

Entire house w/king bed & parking near downtown!

WalkabilityPetsLaundry

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.

4.94 out of 5 average rating, 182 reviews

East End Unit

PetsWalkabilityBreakfast

4.95 out of 5 average rating, 105 reviews

An aerial view displays a colonial home surrounded by vibrant autumn foliage, set on an expansive lawn. The nearby Kennebunk River curves through the landscape, bordered by trees. The property includes a serene setting with open spaces and distant houses visible among the greenery.

Home in Arundel

Classic, calm river view & centrally located home

WalkabilityPetsNearby

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.

4.96 out of 5 average rating, 171 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

WalkabilityOutdoor spacesTV

4.89 out of 5 average rating, 114 reviews

The large, historical home features a spacious outdoor deck adorned with string lights, creating a soft glow during twilight. The manicured lawn is visible in the foreground, while the house showcases a combination of large windows, highlighting the inviting interior ambiance.

Home in Falmouth

Large Historic 7 Bedroom home with Pool & Hot Tub

WalkabilityPetsBarbecue

4.82 out of 5 average rating, 191 reviews

A cozy outdoor patio is presented with a stylish umbrella providing shade over comfortable seating. Plush cushions in varied patterns enhance the seating area, while scenic views of the water and trees are framed in the background, inviting relaxation.

Home in Harpswell

Beautiful Designer's Hideaway on the Maine coast!

PetsOutdoor spacesCondition

An open-concept living area features warm wooden flooring and mid-century style decor. A vibrant orange sofa is positioned opposite a dining table with wooden chairs. Natural light floods in through large windows, and a set of stairs leads to the upper level.

4.98 out of 5 average rating, 407 reviews

3 bedroom house in the heart of Portland

Outdoor spacesPetsIndoor spaces

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 43 reviews

A cozy outdoor area is illuminated by soft string lights and features circular seating around a stone fire pit. The backdrop showcases a charming two-story home nestled among trees, with warm light glowing from the windows, creating an inviting ambiance for evening gatherings.

Home in Sebago

Treehouse Farm - Sebago

PetsOutdoor spacesComfort

Condo in Old Orchard Beach

An aerial view captures the condo community and its proximity to Old Orchard Beach. The clear blue ocean stretches in the background, with sandy shores visible. The surrounding area includes recreational facilities and parking, illustrating the convenient access to nearby attractions.

4.97 out of 5 average rating, 31 reviews

Condo in Old Orchard Beach

PetsWalkabilityCheck-in

Superhost

A spacious living area features warm wood paneling and a cozy wooden fireplace. Comfortable seating is arranged around a coffee table, and large glass doors allow natural light to fill the room, leading to the scenic outdoors. A ladder provides access to the loft area.

Chalet in Bridgton

4.86 out of 5 average rating, 125 reviews

Charming Chalet 3 min to SKIING & PVT beach access

PetsWalkabilityAir conditioning

4.96 out of 5 average rating, 48 reviews

A welcoming log cabin set among trees features a covered front porch with rocking chairs. Red outdoor chairs and a golf cart are visible in the parking area. An American flag hangs from the porch, complementing the natural surroundings and gravel pathway.

Cabin in Frye Island

Secluded Rustic Log Cabin on Beautiful Frye Island

WalkabilityOutdoor spacesPool

Tiny home in Old Orchard Beach

A custom-built home is presented in warm red siding, featuring a welcoming porch with two red chairs positioned near the entrance. Large windows provide natural light, while a picnic table is located on the front yard. The driveway is paved and spacious.

5 out of 5 average rating, 27 reviews

Brand new 2 b/r tiny home, 5 minute walk to beach

WalkabilityPetsGetting around

Place to stay in Shapleigh

5 out of 5 average rating, 137 reviews

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

WalkabilityOutdoor spacesBarbecue

4.93 out of 5 average rating, 121 reviews

A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.

Guest suite in Standish

Steep Falls Escape, river & falls just steps away

PetsWalkabilityBarbecue

4.98 out of 5 average rating, 58 reviews

A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.

Home in Kennebunkport

Lovely Beach house in GRB - Heated pool!

WalkabilityPetsAmenities

Private, pet-friendly home rentals

4.97 out of 5 average rating, 271 reviews

A cozy cottage is surrounded by lush trees and greenery. Two blue chairs are placed outside near the entrance, with a small table between them. A gas grill is positioned nearby, creating a welcoming space for outdoor relaxation and dining.

Cottage in Scarborough

Bright, clean, private cottage near Higgins Beach!

WalkabilityPetsAccess

A charming, two-story home features a traditional design with a light-colored wooden exterior and a steeply pitched roof. Large windows allow natural light to brighten the interior. A green porch is accessible via a set of steps, surrounded by a wooden fence and a large tree providing shade.

4.87 out of 5 average rating, 360 reviews

Private Studio, Portland's East End

PetsWalkabilityParks

4.95 out of 5 average rating, 519 reviews

A beverage sits on a small table beside a glass bottle filled with sticks. The view through a window reveals the sandy beach and calming ocean waves, with a colorful sunset casting soft hues in the sky. An American flag is partially visible in the background.

Cottage in Saco

Deja Blue Guesthouse

PetsOutdoor spacesCheckout

4.98 out of 5 average rating, 81 reviews

Cabin in Freeport

Chickadee A-Frame

Outdoor spacesPetsCleanliness

Condo in Downtown Portland

A decorative fireplace is centered against a light-colored wall, adorned with a framed vintage map above. A small statue and other items rest on the mantel. Natural light streams in from nearby windows, illuminating the wooden floor and a cozy green chair beside the fireplace.

4.93 out of 5 average rating, 200 reviews

Portland 1 Bedroom Condo in the Arts District.

WalkabilityPetsBathroom

4.98 out of 5 average rating, 195 reviews

A wooden deck leads to the entrance of the yurt, featuring two green Adirondack chairs flanking the doors. The surroundings are wooded, with a carpet of forest floor visible and trees providing a natural backdrop.

Yurt in Chebeague Island

Yurt on Chebeague Island

PetsWalkabilityHiking

Apartment in South Portland

A cozy sleeping area features a spacious bed dressed in a navy quilt, complemented by decorative pillows. The green walls are accented by a wooden wall art piece and hanging light fixtures. Nightstands with potted plants add a touch of greenery to the scene.

4.98 out of 5 average rating, 185 reviews

The Knightcap

WalkabilityPetsBathroom