Vacation rentals in Portland
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Quick stats about vacation rentals in Portland
Total vacation rentals
Explore 1,570 vacation rentals in Portland
Nightly prices starting at
Portland vacation rentals start at $30 per night before taxes and fees
Verified guest reviews
Over 197,670 verified reviews to help you choose
Family-friendly vacation rentals
840 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 490 rentals that welcome pets
Vacation rentals with a pool
70 properties feature pools
Rentals with dedicated workspaces
740 properties have a dedicated workspace
Wi-Fi availability
1,530 of Portland vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill 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, Crescent Beach State Park, and Portland Museum of Art
Top-rated vacation rentals in Portland
Guests agree: these stays are highly rated for location, cleanliness, and more.
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.
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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.
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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!
FamilyLocationHospitality
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
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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!
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Historic Home in the West End. Private Parking.
With the Portland Museum of Art and the State Theater a 5 minute walk away, the Old Port just 15, this stunning apartment is just steps from the best eateries, arts & shopping the city has to offer. When you arrive, park your car in the private parking space and forget about it for a while! Built in 1835, this sunny and spacious second-floor apartment features 14-foot ceilings and original hardwood floors. A his and her bathroom is linked with a walk-through stone tiled shower.
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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!
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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.
LocationFamilyAccuracy
Portland Back Cove Hideaway-1 BR- With Patio
Our quiet residential Back Cove neighborhood is your perfect retreat from a busy day exploring Portland. Take a short drive to the center of the city, or enjoy the waterfront walking and biking trail which loops around the cove. Dine at Tipo or Woodford F&B, two neighborhood favorites. Come home to this newly renovated space and relax on the patio! Our space can accommodate four guests. Great for a family, or close friends! We look forward to hosting you!
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Garrison Cove Studio
Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.
ValueFamilyGetting around
The Garden Cabin Tiny Home
Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018
ValueLocationAccess
INCREDIBLE! Waterfront views. 94 walk score.
Wow! Incredible 3 bedroom, 2 bath apartment with working waterfront views. Spacious apartment nestled in Downtown, between the Old Port, Arts District and West End, just steps away from all the highlights of the peninsula. You are just steps away from everything the City has to offer. STHR-000508-2018
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Popular amenities for Portland vacation rentals
What Airbnb hosts recommend seeing in Portland
Find unforgettable activities and unique points of interest near you. Our hosts share their favorite things to do and must-visit places to see in Portland.
Monhegan Island
Historic island with hiking trails, an artist community, and dramatic cliffs
Summarized by AI
On Monhegan Island you can hike 9–20 miles of trails through forest “fairy woods,” seabird habitat to 150-foot ocean cliffs, a lighthouse, and swimming coves. Wander the car‑free dirt roads lined with lobster traps into the village for gift shops, a general store, cafes, and the Monhegan Museum of Art & History. Visit artists’ studios, galleries, and the crafts co‑op in the art colony, then refuel with seafood on Fish Beach and beer at Monhegan Brewing. The ferry ride adds open‑ocean views and chances to spot whales, porpoises, or puffins.
Pine Point Beach
Expansive sandy beach with a tranquil vibe, perfect for long walks, swimming, and exploring sandbars
Summarized by AI
At Pine Point Beach you can spread out on a long, soft, sandy shoreline that’s great for swimming, sand play, and quiet walks along the ocean. Explore the large sandbar at low tide, or enjoy warmer, swimmable water and gentle waves at high tide. You’ll find a designated parking lot, paid parking, public restrooms, outside showers, and a small snack shack/concession in summer. Walk for miles toward Old Orchard Beach, or wander the quieter end by the river inlet and dunes.
Coastal Maine Botanical Gardens
Expansive botanical garden offering themed gardens, woodland trails, and whimsical troll sculptures
Summarized by AI
Spend the day exploring hundreds of acres of ornamental gardens, children’s and sensory gardens, native wildflowers, impressive waterfalls, stonework, and miles of waterfront and woodland trails. Kids can hunt for giant wooden troll sculptures, visit the Native Butterfly House, play in the Bibby and Harold Alfond Children’s Garden, and even build fairy houses in the woods. Enjoy on-site cafés with lunch, snacks, and adult beverages, plus art exhibits, a great gift shop, and the seasonal Gardens Aglow/Festival of Lights. Check the website for hours, bloom updates, timed tickets, reservations, and animal policies.
Willard Beach
Charming sandy beach with scenic views, dog-friendly hours, and nearby local eateries
Summarized by AI
At Willard Beach you can spread out on the soft sand, swim in the famously cold and refreshing Casco Bay water, or just sit and watch boats coming and going with views of Cushing Island, Peak’s Island, Ram Island Light, and Portland Head Light in the distance. Launch a kayak or paddle board, let kids enjoy the playground, and grab ice cream, hot dogs, or snacks at the seasonal snack bar. Dog lovers can visit during off-leash hours for an easygoing, local scene. From the beach, follow the walking path along the shore to Spring Point Ledge Light, or wander to nearby Willard Square for Scratch Bakery and other local shops.
Popham Beach, Phippsburg
Expansive sandy beach with tidal pools, island walks, and scenic views
Summarized by AI
At Popham Beach State Park you get a wide, white-sand beach with great swimming, body surfing, and long walks, plus changing rooms, real bathrooms, solar rinse-off showers, and charcoal grills. Visit at low tide for huge sandbars, tidal pools ideal for toddlers, and the chance to walk out to Fox Island and other nearby islands—just watch the tide charts and rip currents. Kids can build sandcastles, explore driftwood, and look for tidepools. Nearby, pair your beach day with Fort Popham or local spots like Spinney’s Restaurant and Winnegance Restaurant and Bakery.
Reid State Park
Scenic park with sandy beaches, tidal pools, hiking trails, and picnic areas
Summarized by AI
At Reid State Park you can stretch out on rare long sandy beaches like Mile and Half Mile, walk over a mile of shore, and choose between big surf, cold ocean swimming, or a calmer, slightly warmer tidal lagoon. Explore rocky cliffs and tidepools, climb driftwood structures, hike peaceful wooded trails, and watch seabirds around the salt marshes and dunes. Pack a picnic for the shady tables or grills, let kids scramble on rocks, and rinse off in the clean bathrooms, changing rooms, and showers.
Portland oceanfront vacation rentals
Oceanfront Escape • Walk to Beach • Sleeps 14
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Higgins Beach *New* Beach Home & Private Offices
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Waterfront Gem walkable to Restaurants!
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Beautiful Kettle Cove Apt Steps to Beaches
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Deja Blue Guesthouse
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Edgewater Retreat - Lakefront w/Sauna & EV Charger
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Luxury Beach Front Condo! Prime Location!
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Beekeeper's Cottage- Peaceful,Quiet - Ocean Front
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Private Portland vacation rentals
Luxury Year-round Treehouse with private hot tub
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Crow's Nest
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Upscale City Apartment. Central location
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Mary J. Eastburn House--Baxter Suite
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Crescent Beach Gardens
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Quiet Comfy Victorian Escape
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Harborview - Curated East End Escape w/ Parking
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Peaks Island Master Bedroom Suite
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Portland house rentals
Secret Carriage House in Perfect Location!
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"Good Vibes" 4 Wonderful Seasons @ Portland Home!
ValueFamilyCleanliness
Explore Portland from a 18th-Century Victorian
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Easy Old Port Access & Casco Bay View Craftsman
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Moss House: A Modern Waterfront Cabin in the Woods
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Luxury Home w/HOT TUB & Fire Pit
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Fore River Getaway
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An Airy Private Suite steps off Washington Ave
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When is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 | $150 | $151 | $171 | $205 | $250 | $285 | $290 | $245 | $229 | $181 | $169 |
| Avg. temp | 24°F | 26°F | 34°F | 45°F | 55°F | 64°F | 70°F | 69°F | 62°F | 50°F | 40°F | 30°F |
Frequently Asked Questions
What are the best places to stay in Portland?
Explore the Old Port for historic brick streets and harbor views, or look to the West End for charming architecture and tree-lined avenues. Munjoy Hill is often recommended for its relaxed vibe and proximity to cafes and green spaces.
What are the best things to do in Portland with kids?
Families often explore the Children's Museum and Theatre of Maine, enjoy hands-on marine exhibits at the local science center, or picnic in one of the city’s waterfront parks. Lighthouse visits and ferry rides are also frequently suggested for all ages.
What are some of the best things to do in Portland?
Wander the Old Port’s cobblestone streets, explore art at the Portland Museum of Art, and sample locally rooted seafood at the city’s markets. The Eastern Promenade draws many for bay views and walking paths.
How is the weather in Portland?
Portland has chilly winters near 16–32°F (-9–0°C) with frequent snowfall, while summers are mild with highs around 80°F (26°C) and comfortable evenings. Spring and autumn are often cool and can bring rain, so packing layers is recommended.
What are the best places to visit in Portland?
Explore the Portland Head Light, wander the Old Port district, and take in displays at the Portland Museum of Art. The Eastern Promenade is also frequently suggested for its scenic bay views.
What are some hiking trails in Portland?
The Eastern Promenade has popular walking and biking trails overlooking Casco Bay, while Evergreen Cemetery’s woodland paths blend history and nature. Baxter Woods is also frequented for its shaded trails and birdwatching spots.
What are some family activities we can do in Portland?
Families often visit the Children's Museum and Theatre of Maine, explore hands-on science exhibits, or enjoy boat rides around the harbor. Public parks and seasonal outdoor concerts are also welcoming for all ages.
What are some of the best day trip ideas from Portland?
Consider exploring nearby islands in Casco Bay, relaxing on local beaches, or visiting state parks just outside the city. Lighthouses and small coastal towns around Portland frequently draw visitors seeking New England charm.
Are there any pet friendly accommodations available in Portland?
Pet-friendly vacation rentals can be found in many neighborhoods such as Munjoy Hill, West End, and areas near the waterfront. Parks and walking trails nearby make it convenient to explore with your pet.
What are some local tips for visiting Portland?
Dressing in layers is helpful due to changing coastal weather, and comfortable shoes are useful for walking the city’s brick streets. Weekdays or early mornings in the Old Port can feel quieter compared to weekends.
What is Portland known for?
Portland is known for its vibrant food scene, working waterfront, and historic architecture. The city’s lighthouses, arts community, and scenic harbor are also well recognized.
What are the best hidden gems to explore in Portland?
Discover Fort Gorges on an island in Casco Bay, browse artisan studios in the East End, or explore the quiet trails of Baxter Woods. Small galleries and local coffee shops around Munjoy Hill add to the city’s creative spirit.
What are the best foods to try in Portland?
Portland is known for fresh lobster rolls, clam chowder, and baked goods from local bakeries. Many enjoy tasting locally made cheeses, craft beers, and seasonal seafood at neighborhood markets and restaurants.
What should I bring for a trip to Portland?
Pack layers for shifting coastal weather, a rain jacket, and comfortable shoes for city walks. A warm hat and gloves are helpful from autumn through early spring, especially along the waterfront.
What is the nightlife in Portland like?
Portland has lively breweries, live music venues, and bars clustered in the Old Port and Arts District. Locally owned restaurants and performance spaces often set a welcoming evening scene.
What are the most popular events or festivals in Portland?
Portland has several well-known events, including local seafood celebrations, arts festivals in neighborhoods like the Old Port, and summer concerts on the waterfront. Holiday markets and music gatherings are frequently suggested, especially in warmer months. Community spaces often host seasonal programming.
Are there family friendly vacation rentals in Portland?
Many vacation rentals around Portland are suitable for families, with options in neighborhoods such as Munjoy Hill, the West End, and areas near local parks. Some homes feature multiple bedrooms and easy access to family attractions.
When is the best time to visit Portland?
Late spring through early fall is often recommended, with milder temperatures and active waterfront events. Fall foliage draws many visitors, while winter brings a quieter city atmosphere and seasonal festivities.
All about Portland
Perched along the dramatic slate-gray waters of the Atlantic Ocean, where gulls wheel and whitecaps dot the surf, Portland is quintessential Maine combined with the allures of a metropolis. Established as a booming port town by traders and fishermen, Portland is now the state’s biggest city. Here you can tread cobblestone streets, visit historic lighthouses, and dine on lobsters hauled from the nearby waters. But you’ll also find top-notch museums and galleries, boutique shopping, and a celebrated foodie scene that boasts award-winning restaurants and a thriving microbrew culture. New and old Maine commingle comfortably here, where you can enjoy the best of both worlds.
What are the top things to do in Portland?
Portland Head Light
The Portland area is home to several historic lighthouses, but the Portland Head lighthouse is the undisputed heavyweight. Construction began in 1790, making it the oldest in the state. Visitors can tour the quaint lighthouse and its grounds, which include the former keepers’ house, now repurposed as a museum. Take in the sweeping vista, which includes views of four more lighthouses and the possibility of watching lobstermen pulling their traps from the bay, before taking a scenic stroll through Fort Williams, the 90-acre park in which the lighthouse resides.
Casco Bay and the Calendar Islands
Hop on a ferry (or charter a water taxi) to tour the photogenic Calendar Islands, clustered in grand Casco Bay. You can experience small-town Maine life here. Teensy Cliff Island has fewer than 60 year-round residents and a small schoolhouse. Peaks Island offers four miles of uninterrupted coastline and historical sites such as a World War II artillery bunker. Tonier Great Diamond Island, where a private community has been installed within the refurbished military buildings of historic Fort McKinley, boasts upscale dining. Don’t have time to set ashore? Casco Bay Lines, the island ferry service, offers speciality cruises that will afford you a sailor’s-eye view of the islands and dazzling bay.
Old Port District
Travel back in time in this quaint maritime neighborhood that still looks very much the way it did in the early 19th century. Narrow cobblestone streets and historic brick warehouses lend the enclave its cozy feel, but that’s where the frozen-in-time vibe ends. The restored Old Port District, which is on the National Register of Historic Places, is home to quirky boutiques, inventive eateries, and brewpubs. You’ll find many of these offerings on buzzy Exchange Street.
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- Scarborough Beach
- Footbridge Beach
- Cape Neddick Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Gooch's Beach
- Cranmore Mountain Resort
- Hills Beach
- Fortunes Rocks Beach
- King Pine Ski Area
- Wallis Sands Beach
- Conway Scenic Railroad
- Pleasant Mountain Ski Area
- Popham Beach State Park
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