Pet-friendly holiday rentals in Portland

4.96 out of 5 average rating, 171 reviews

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 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

WalkabilityOutdoor spacesBarbecue

4.9 out of 5 average rating, 324 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

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

WalkabilityOutdoor spacesFamily

4.92 out of 5 average rating, 301 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!

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

WalkabilityPetsCheck-in

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.

PetsWalkabilityKitchen

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

Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

WalkabilityOutdoor spacesLong stay

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, 539 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.

WalkabilityPetsDecor

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

PetsWalkabilityTV

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.

PetsWalkabilityLocation

4.98 out of 5 average rating, 193 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!

WalkabilityOutdoor spacesAccess

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.

WalkabilityPetsAccuracy

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, 517 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!

WalkabilityOutdoor spacesQuiet

4.79 out of 5 average rating, 657 reviews

A spacious bedroom features a queen bed with white linens and a soft blue throw. A study desk is positioned near the large windows, allowing natural light to fill the room. A comfortable dish chair and a small plant add a refreshing touch to the space.

Apartment in West End

Downtown Studio, Parking with EV charger

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

PetsWalkabilityNearby

Popular amenities for Portland pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 173 reviews

Home in West End

Entire house w/king bed & parking near downtown!

WalkabilityOutdoor spacesCleanliness

4.95 out of 5 average rating, 106 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

PetsOutdoor spacesBackyard

4.95 out of 5 average rating, 265 reviews

Home in Bridgton

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Outdoor spacesLaundryTV

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!

WalkabilityPetsLaundry

4.98 out of 5 average rating, 407 reviews

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.

Home in Portland

3 bedroom house in the heart of Portland

PetsWalkabilityLaundry

4.92 out of 5 average rating, 102 reviews

The exterior of a historic farmhouse is presented, featuring two stories with white trim around multiple windows. A central front door is flanked by light fixtures, and landscaped greenery, including hostas, surrounds the entrance. A well-maintained lawn adds to the inviting aspect of the property.

Home in Falmouth

Wild Rose Farm -Three Queen Suites

Outdoor spacesPetsAmenities

4.96 out of 5 average rating, 205 reviews

An open living area features a light-filled space with high ceilings and large windows. A neutral-colored sofa offers comfortable seating, complemented by a wooden dining table with stools. A contemporary refrigerator and kitchen area are visible, along with decorative elements such as a plant and a flower bouquet.

Home in Freeport

Spacious Costal Home in Freeport, ME

Outdoor spacesWalkabilityBreakfast

4.88 out of 5 average rating, 108 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

PetsOutdoor spacesBeach

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

Outdoor spacesPetsAir conditioning

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

PetsWalkabilityLocation

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

4.87 out of 5 average rating, 127 reviews

Charming Chalet 3 min to SKIING & PVT beach access

WalkabilityPetsKitchen

5 out of 5 average rating, 6 reviews

Home in Bridgton

The Nest | Lake Access, Pool, HotTub, 5BDRM, Sauna

WalkabilityAmenitiesHospitality

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

WalkabilityPetsIndoor spaces

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, 28 reviews

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

PetsWalkabilityCondition

Place to stay in Shapleigh

5 out of 5 average rating, 137 reviews

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

WalkabilityPetsSleep quality

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!

WalkabilityOutdoor spacesView

Private, pet-friendly home rentals

4.97 out of 5 average rating, 124 reviews

Tiny home in Gorham

The Chickadee | Upscale Tiny Home Near Portland

Outdoor spacesPetsBathroom

4.97 out of 5 average rating, 272 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!

Outdoor spacesPetsHospitality

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.

4.9 out of 5 average rating, 172 reviews

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

WalkabilityPetsFamily

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, 359 reviews

Private Studio, Portland's East End

Outdoor spacesWalkabilitySolo travel

4.95 out of 5 average rating, 523 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

WalkabilityOutdoor spacesIndoor spaces

Superhost

A modern living space is displayed, featuring a comfortable sofa and a wicker coffee table. Seating options include armchairs and a dining set with four chairs. A fan is mounted on the ceiling, and decorative elements, like a wall mirror and a piece of artwork, add to the ambiance.

Apartment in Downtown Portland

4.94 out of 5 average rating, 158 reviews

New 2 Bedroom Apartment in Heart of West End

WalkabilityPetsComfort

Guest suite in South Portland

A serene beach scene is captured, featuring a gentle shoreline with soft sand. Small boats are anchored in the calm water, while a lush green landscape forms the backdrop under a partly cloudy sky. Sunlight reflects off the waves, creating a sparkling effect.

4.92 out of 5 average rating, 428 reviews

Apartment Walking Distance to Willard Beach

WalkabilityPetsSleep quality

The image captures a tree-lined street with a view of the ocean in the background. A charming duplex is featured, having welcoming grey and white siding. A porch with decorative railings leads to the entrance, while nearby flowering plants add a touch of color to the scene.