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Vacation rentals in Portland

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Top-rated vacation rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cottage in Brunswick
5 out of 5 average rating, 203 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favorite
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
5 out of 5 average rating, 216 reviews

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.

Top guest favorite
An A-frame cabin is illuminated at night, featuring soaring ceilings and large windows. The exterior is surrounded by trees, with a warm firepit in the foreground. Two adirondack chairs are positioned nearby, providing a cozy setting for outdoor gatherings.
Cabin in Freeport
5 out of 5 average rating, 104 reviews

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!

Top guest favorite
An open living space is illuminated by natural light, featuring a cozy sofa and two accent chairs. A dining area is visible alongside the modern kitchen with a spacious island. Large windows offer views of the outdoors, enhancing the inviting atmosphere.
Apartment in East End
4.98 out of 5 average rating, 124 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!

Top guest favorite
A bright sitting room features large windows that invite natural light and offer views of the harbor. A round table with two chairs occupies the space, alongside a built-in seating area with cushions. A door leads to an outdoor deck, enhancing indoor-outdoor connectivity.
Guest suite in West End
4.99 out of 5 average rating, 361 reviews

Sunny West End Guest Suite w/Harbor Views and Pool

Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

Top guest favorite
A charming exterior of a black post and beam barn is displayed featuring a natural wood door with metal hardware. A decorative star adorns the upper section of the barn, while a small metal bench sits on a gravel pathway beside the structure.
Barn in Stroudwater
5 out of 5 average rating, 468 reviews

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 newly created 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 glass of wine under the splendid backyard grape arbor.

Top guest favorite
An elevated queen bed is showcased with a white comforter and a decorative pillow. Natural light filters through a large window above, accompanied by small potted plants. A wooden staircase leads to a different area, enhancing the studio's overall spacious feel.
Guest suite in Ferry Village
5 out of 5 average rating, 295 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

Guest favorite
Apartment in Downtown Portland
4.9 out of 5 average rating, 440 reviews

Central-Local Studio in Vibrant Portland, Maine!

Spacious and private studio apartment, with sitting area, queen size bed, table and chairs for dinning, kitchen and full bathroom. Newly updated appliances in a well maintained building. Wood floors lend charm, while modern decor makes for a contemporary feel. This comfortable space is perfect to come back to after exploring the surrounding neighborhood. The Studio is steps away from Portland's best restaurants, shops, nightlife and more!

Guest favorite
Apartment in East End
4.92 out of 5 average rating, 279 reviews

Oceanside Open Concept 2BR- East End/ Downtown

Classic New England style home, recently renovated and updated with modern amenities. A stone's throw from the best public space in all of Portland, the Eastern Promenade. The Promenade boasts beautiful ocean views, food trucks, a public beach, basketball & tennis courts & large playground. The neighborhood offers great restaurants and coffee shops. The Old Port and rest of downtown is a 10 minute walk or 4 minute Uber ride away.

Top guest favorite
A cozy living area features a grey sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, and a large window allows natural light to fill the space, offering a view of the trees outside. A piece of modern art hangs on the wall.
Apartment in West End
4.98 out of 5 average rating, 201 reviews

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.

Guest favorite
A welcoming living area is framed by sloped ceilings and large windows, allowing natural light to fill the space. Comfortable sofas are arranged around a coffee table, while decorative plants add a touch of greenery. A mirror reflects the inviting atmosphere.
Condo in Downtown Portland
4.92 out of 5 average rating, 184 reviews

Coastal Penthouse - Center of Downtown Portland!

Overlooking Portland’s historic downtown rests this coastal penthouse located on the most vibrant street in the city! This one-bedroom apartment is fitted out with all of the amenities needed for a Maine vacation! Enjoy relaxing in luxury while only feet away from Portland’s most popular destinations. This penthouse is perfect for those here for business or a Maine getaway!

Guest favorite
Apartment in East End
4.87 out of 5 average rating, 303 reviews

Petit Pad Atop Munjoy Hill+Steps to Eastern Prom!

Our space is small yet cozy. Tiny living at its best. It's bright with many windows lending a glimpse of Casco Bay, and the third floor level welcomes the cool breeze off the water. Well appointed with everything you need to be comfortable and feel at home. A perfect home base while you explore Portlands Munjoy Hill neighborhood and beyond! We know you'll love it!

Popular amenities for Portland vacation rentals

When is the best time to visit Portland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,383 GYDG$30,337 GYDG$31,383 GYDG$35,568 GYDG$42,890 GYDG$50,632 GYDG$59,628 GYDG$60,674 GYDG$51,259 GYDG$47,912 GYDG$37,869 GYDG$35,358 GYD
Avg. temp-4°C-3°C1°C7°C13°C18°C21°C21°C16°C10°C4°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$6,277 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

Destinations to explore

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