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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
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
The modern tiny home features a sleek exterior with horizontal siding and a dark roof. Two chairs are positioned on the covered entryway, accompanied by a small table adorned with a pot of flowers. Lush green grass surrounds the home, complemented by a newly paved pathway.
Tiny home in Scarborough
4.98 out of 5 average rating, 110 reviews

Cozy Tiny Home | Fireplace • 9 Miles to Portland

This unique cottage has a style all its own. Discover modern comfort in our brand-new suburban tiny home located in The Downs in Scarborough, ME! This stylish space offers all-new amenities and a cozy atmosphere. Ideal for solo travelers or couples, but can accommodate up to four guests. Enjoy a private escape while being ~9 miles from Portland and ~6 miles from the beach. Experience efficient living without compromising on luxury. Book now for a fresh, contemporary getaway!

Top guest favorite
An open dining area features a round wooden table surrounded by blue chairs. A comfortable living room area is visible, with a gray sofa and art on the walls. Large windows allow natural light to brighten the space, enhancing the modern design.
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.

Guest favorite
A serene bedroom is furnished with a comfortable queen bed dressed in neutral linens and accent pillows. Warm tones are complemented by decorative wall hangings, while a large mirror and plants enhance the light-filled space. A cozy chair and woven basket add to the inviting atmosphere.
Apartment in Back Cove
4.89 out of 5 average rating, 142 reviews

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!

Top guest favorite
A comfortable seating area features a woven chair and a plush sofa beside a small round table. Natural light filters through large windows, illuminating the space. In the background, an open doorway leads to a dining area with a dining table and chairs.
Apartment in East End
4.85 out of 5 average rating, 287 reviews

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!

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
A studio apartment is presented with a queen size bed adorned with a muted blanket. A cozy sitting area includes a light grey sofa, while a small dining table with chairs occupies a portion of the space. A bookshelf is visible, enhancing storage and decor.
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!

Top guest favorite
The entryway showcases a blend of modern and rustic elements, featuring a wooden accent wall and exposed brick. A low wooden bench and a round coffee table are positioned on a textured carpet, while a bank of mailboxes is mounted on one side, offering convenience for residents.
Condo in Downtown Portland
4.86 out of 5 average rating, 375 reviews

Old Port on foot

Newly renovated, spacious and modern top-floor condo in a posh historic building in the heart of downtown Portland. Leave your car behind! Walking distance to tons of bars/restaurants, stores, a block from the Portland Harbor/Commercial St and 3 blocks from Merrill Auditorium. Please note there is an additional $50 cleaning charge for stays greater than 7 nights. For stays greater than 14 nights, the cleaning fee is $180.

Guest favorite
A bright living room features neutral-colored walls and hardwood flooring. Comfortable seating options include a dark gray couch and armchair, complemented by a patterned area rug. A flat-screen TV is mounted on the wall, and large windows allow natural light to fill the space.
Apartment in East End
4.86 out of 5 average rating, 231 reviews

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.

Top guest favorite
The spacious great room features large windows that showcase views of the sunset and Portland skyline. A wooden dining table is set beside a cozy seating area, while soft lighting from lamps creates a warm ambiance. Unique decor adds character to the inviting space.
Guest suite in East End
5 out of 5 average rating, 209 reviews

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.

Top guest favorite
A bright hallway features wooden flooring and natural light filtering through large windows. Exposed wooden beams and a brick wall add character. A cozy seating area with red sofas is visible at the end, alongside a modern kitchen space. A bathroom door is located to the left.
Apartment in Downtown Portland
4.94 out of 5 average rating, 731 reviews

Extraordinary Architectural Masterpiece Downtown

Dan's place is close to nightlife, public transport, the city center, and parks. You’ll love his place because of the ambiance, the outdoors space, the light, the neighborhood, and the comfy bed. The suite is perfect for couples, solo adventurers, and business travelers.

Popular amenities for Portland vacation rentals

When is the best time to visit Portland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,393 GYDG$30,346 GYDG$31,393 GYDG$35,579 GYDG$42,904 GYDG$50,647 GYDG$59,647 GYDG$60,693 GYDG$51,275 GYDG$47,927 GYDG$37,881 GYDG$35,369 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$6,279 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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