
Vacation rentals in Portland
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Top-rated vacation rentals in Portland
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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!

Cozy SoPo Condo
Welcome to this cozy one-bedroom apartment in Ferry Village, South Portland, Maine. This charming neighborhood is located just across the Casco Bay from Portland, and it's the perfect place to relax and admire the natural beauty of Maine. Enjoy a tour of our gardens and relax on the string light lit patio. The apartment is located on a quiet street, less than a mile walk from Willard Beach. Take a walk on the Greenway to Bug Light park or towards Knightville for some food and drink options.

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!

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.

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.

Romantic Bungalow w/ Hot Tub & Parking
The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom
Beach vibes in this cozy space make for a comfortable home base while you explore Portland's Munjoy Hill neighborhood. The apartment is situated in the East End, a short walk to the Eastern Promenade, local grocery, great restaurants and bakeries. Head to the East End Beach, or paddle to the islands in Casco Bay. Walk to the Old Port from this quiet neighborhood in 15 minutes or head over to Washington Ave, for amazing food, distilleries and breweries!

Downtown Historical Victorian 2 BR APT
The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Oceanside Modern Victorian 2BR- East End/ Downtown
Classic New England style home, recently renovated and updated with modern amenities. A stone's throw from Portland's best public park, The Eastern Promenade. The Promenade boasts beautiful ocean views, a public beach, basketball & tennis courts & large playground. The neighborhood offers great restaurants and coffee shops. The Old Port and the rest of Downtown Portland is a 10 minute walk or 4 minute Uber ride away.

Beautiful West End studio, hot tub, free parking
Charming, comfortable, well-appointed studio, in an historic building, just steps away from everything downtown Portland has to offer: restaurants, museums, shopping, galleries, parks, Congress Street, and the Old Port. Close to Maine Medical and Mercy Hospital, the Portland Expo, Sea Dogs stadium, and Deering Oaks Park. The studio rental includes free parking for one car and exclusive use of a hot tub.

Sunset Suite 42
Breathtaking views, privacy, and convenient location make Sunset Suite a great place to be while visiting ME! The great room with a cathedral ceiling and skylights offers the best of natural light... day and night! The Portland skyline is all yours from your private and expansive deck as you put your feet up and reminisce about your day and plan for the next.

Self-check-in | Desk | Washer + Dryer | Kitchen 2
This prime space is located a block from Deering Oaks Park, just down the street from Maine Medical Center, the Western Promenade, close to many restaurants, bars & cafes in the neighborhood. Since the apartment is located in the heart of Portland, you can expect typical city noise from pedestrians, cars, and emergency vehicles.
Popular amenities for Portland vacation rentals
Stay near Portland's top sights
Private vacation rentals in Portland

Light-Filled Getaway with Private Porch

Old Port on foot

Solar Suite surrounded by Nature

Walk-able Portland Studio

Private Sauna+Near Beach+FirePit+Forest View+Pond

Cottage Under a Crabapple Tree

Falmouth Waterfront Carriage House Apt

Historic Munjoy Hill Retreat-Rooftop Water Views.
Portland oceanfront vacation rentals

Luxury Beach Front Condo! Prime Location!

Waterfront Gem walkable to Restaurants!

Oceanfront Condo with Awesome Views

Drakes Island Beach Front Breathtaking Property !

Deja Blue~Guest Beach House

Tiny Cottage Across The Street From Beach

Beautiful Kettle Cove Apt Steps to Beaches

LUX Designer Private Waterfront
House rentals in Portland

Cozy Cottage Retreat near Breweries & Airport

Luxury Home w/HOT TUB & Fire Pit

Wren Cabin + Wood fired Sauna

Winter Dates: Cozy and Peaceful Island Getaway

2 bed house w/king bed, pets & off-street parking!

Distinctive Home & Garden

Beautiful Coastal Maine Getaway

3 bedroom house in the heart of Portland
When is the best time to visit Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,367 GYD | G$30,321 GYD | G$31,367 GYD | G$35,549 GYD | G$42,868 GYD | G$50,605 GYD | G$59,597 GYD | G$60,642 GYD | G$51,232 GYD | G$47,887 GYD | G$37,849 GYD | G$35,340 GYD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
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.
Quick stats about vacation rentals in Portland

Total vacation rentals
Explore 1,600 vacation rentals in Portland

Nightly prices starting at
Portland vacation rentals start at G$6,273 GYD per night before taxes and fees

Verified guest reviews
Over 194,630 verified reviews to help you choose

Family-friendly vacation rentals
860 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 460 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
820 properties have a dedicated workspace

Wi-Fi availability
1,570 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, Portland Museum of Art, and Crescent Beach State Park
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- Sebago Lake
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