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From $1153 per night (USD)
VRBO
Spacious 7-bedroom house in marvelous Portland with AC, WiFi
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Experience Portland in comfort and style with this spacious 3-unit home, perfect for large groups of 16+. Spread out acr ...
From $1153 per night (USD)
VRBO
From $126 per night (USD)
Expedia
In-town no frills 2 bedroom apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Clean, simple & walkable to all in-town Portland restaurants, venues & neighborhoods. A 3rd floor walk up no frills apa ...
From $126 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Beautiful Apartment on Munjoy Hill
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
City of Portland License Number: STHR-006186-2024 Stay at our stylish 3rd-floor apartment on the east end, a retreat in ...
From $297 per night (USD)
VRBO
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Expedia
Charming Towhome on Historic Diamond Cove
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax on the covered porch or enjoy the inviting living spaces. This peaceful retreat is accessible only by boat, offeri ...
Click For Pricing
Expedia
From $246 per night (USD)
VRBO
Peaceful & minutes from the Old Port with private parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1 sunny bedroom apartment is located in the peaceful neighborhood of Knightville. There are several excellent dinin ...
From $246 per night (USD)
VRBO
From $293 per night (USD)
Expedia
NEW 1 BDR-Heart of Munjoy Hill
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This very quiet, recently fully renovated unit sits upon the highest point of Munjoy Hill/East End. It includes 1 bedro ...
From $293 per night (USD)
Expedia
From $483 per night (USD)
VRBO
Bright, updated century old cottage two blocks from the ocean
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
*Transitioning from other STR site to VRBO so reviews and ratings are on that platform. Newly renovated 2 bedroom cotta ...
From $483 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Walkable 2-bed in downtown Portland. Washer and dryer in apartment.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
At our rental we leave lots of towels for each guest. We do not ask our guests to clean the apartment. We provide delici ...
From $190 per night (USD)
Expedia
From $1910 per night (USD)
VRBO
Charming Historic Estate | Perfect for Getaways, Micro-Weddings & Events
Bedrooms:
4
Bathrooms:
10
Sleeps:
18
Summary: Welcome to your home base in coastal Maine—an elegantly restored historic property just steps from Portland’s v ...
From $1910 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Brews, Art & Fun! Downtown Stay Right in the Heart of Portland!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay in the heart of Portland for direct access to its rich history and vibrant culture. Enjoy the historic Old Port, fa ...
From $273 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Spotless Victorian on William
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Spotless Victorian on William, a meticulously maintained apartment in one of Portland’s most charming in-town ...
From $250 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Charming Studio apartment with WiFi, AC in welcoming Portland
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy Portland's East End like a local with this stunning open-concept apartment as your home base! Located in the heart ...
From $149 per night (USD)
Expedia
From $612 per night (USD)
VRBO
Spacious 4-bedroom house located in the heart of Portland, ME.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Unwind in Portland at this delightful house. With 4 bedrooms including 1 king, 2 queen, and 1 twin bed, along with 3 bat ...
From $612 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Luxurious 2BR Penthouse / Ocean Views / East End
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this stunning 3rd-floor penthouse with breathtaking panoramic views of Casco Bay. With rare private parking an ...
From $477 per night (USD)
Expedia
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VRBO
Munjoy Hill Escape Walk to Eastern Promenade
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Modern Condo on Munjoy Hill Spacious and inviting 2-bedroom, 1-bathroom condo that sleeps 4 in 2 KING beds, located just ...
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VRBO
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Expedia
Mint Ocean Promenade Condo, Steps to Old Port
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover the perfect blend of comfort and convenience in this modern 2-bedroom condo located in the heart of Munjoy Hill ...
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Expedia
From $239 per night (USD)
VRBO
Studio Unit Walkable Everywhere
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Recently updated clean & no frills 1st floor unit in a 3 floor brick building walkable to all in-town Portland hot spots ...
From $239 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Private Entrance Residential Portland
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A great, simple1 bedroom apartment in a 3 unit building located in quiet suburban neighborhood of outer Portland. A 10-1 ...
From $167 per night (USD)
Expedia
From $3022 per night (USD)
VRBO
Steps to the Sand, Modern Home on Willard Beach, Fenced in Yard, Deck & Grill
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Wake up to the sound of waves, enjoy coffee with ocean views, and step out onto the soft sands of Willard Beach—just a 3 ...
From $3022 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Willard Beach: Cozy Apartment with a King Size Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provide ...
From $334 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Willard Beach–Private Apt Near Portland & Parks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Many guests have remarked that this stylish, first floor apartment is much larger than it appears in the photos. Just a ...
From $223 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Your Portland adventure begins at this 2-bedroom apartment. The space features 2 queen beds, AC, heating, WiFi, and a sh ...
From $279 per night (USD)
Expedia
From $872 per night (USD)
VRBO
New - Cozy Cape on Peaks Island overlooking Casco Bay and Portland skyline
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
The whole group will enjoy easy access to everything from this centrally located, charming cape overlooking Casco Bay an ...
From $872 per night (USD)
VRBO
From $253 per night (USD)
Expedia
2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom apartment in Portland. The space features 2 cozy queen beds, WiFi, heating, and AC. ...
From $253 per night (USD)
Expedia
From $945 per night (USD)
VRBO
Downtown Portland Retreat | 3 Units | Near Breweries & Scenic Harbor!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $945 per night (USD)
VRBO
From $598 per night (USD)
VRBO
2 Family Ready Rooms | Pet-Friendly Stay, Walking Distance to Museum of Art
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $598 per night (USD)
VRBO
From $598 per night (USD)
VRBO
Pet-Friendly Stay | 2 Units | Close to Victoria Mansion & Lighthouse!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $598 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Stylish Stay | Savor Seafood & Explore Portland’s History!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $273 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Downtown Portland Stay | 1 Unit | Near Commercial Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the heart of Portland, this modern hotel offers easy access to the Old Port district and the Portland Museum ...
From $273 per night (USD)
VRBO
From $1260 per night (USD)
VRBO
4 Cozy Units | Downtown Stay, Waterfront & Near Vibrant Old Port District
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $1260 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Relaxing Couple Pet-Friendly Stay | Seafood & Portland Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay in the heart of Portland for easy access to the Old Port's charm, top breweries, and beautiful waterfront. Discover ...
From $273 per night (USD)
VRBO
From $378 per night (USD)
VRBO
Near Portland Trails: Walkable Apartment w/ Deck
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Open Layout | In-Unit Laundry | 1/2 Mi to Restaurant & Market | BBQ Ready Discover Portland, ME, like a local at this 1 ...
From $378 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Beautiful Unit in Serene Countryside Setting Near Wineries – Onsite Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore Maine's coastal charm with nearby wineries and breweries, or stroll through Old Port for the perfect blend of se ...
From $215 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Sauna & fire table near Portland's Back Cove
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sunny open space, near Payson Park & Back Cove. Enjoy the newly added sauna in the backyard, surrounded by nature and st ...
From $455 per night (USD)
Expedia
Click For Pricing
VRBO
3BR + Balcony + Workspace + Parking + 10Min Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy 1,700 square feet of comfortable, thoughtfully designed living in the heart of Portland, Maine. Perfect for famili ...
Click For Pricing
VRBO
From $1464 per night (USD)
Expedia
6BR Sleeps 16 w/ Balcony 10 mins to Downtown
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Bringing everyone together? This 6BR, 4.5BA setup combines two private apartments in the same building—perfect for group ...
From $1464 per night (USD)
Expedia
From $332 per night (USD)
VRBO
State of Charm | Historic West End Haven
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience Portland’s charm in this beautifully restored 2 bed, 1.5 bath Victorian apartment in the heart of the downtow ...
From $332 per night (USD)
VRBO
From $540 per night (USD)
Expedia
Lofty Ambition | Stunning West End Rooftop Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into this dazzling retreat perched atop Portland’s historic West End! Bathed in sunlight and bursting with characte ...
From $540 per night (USD)
Expedia
From $109 per night (USD)
VRBO
Historic Charm at 236 - Elegant West End Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Stay in the heart of Portland’s historic West End at an iconic landmark property, blending Victorian charm with modern c ...
From $109 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Luxury on Back Cove - Three Gables
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Live like a local in this grand, two‑level flat on a quiet, tree‑lined street 5 minutes from Portland’s buzzing Old Port ...
From $267 per night (USD)
Expedia
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VRBO
Chic & Cozy Luxury Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Settle into the Chic & Cozy Luxury Retreat, a stylish and fully equipped home in Portland, Maine, designed for mid- to l ...
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VRBO
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Expedia
Breeze & Blue: A Refreshing Portland Escape
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Settle into this spacious 2‑bedroom Portland retreat just minutes from the Old Port and a short walk to the Back Cove Tr ...
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Expedia
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VRBO
Coastal Nest: 1-Bedroom Apartment in Portland
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your stylish 1-bedroom retreat in Portland, Maine! This spacious apartment offers a perfect blend of comfort ...
Click For Pricing
VRBO
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Expedia
Modern Comfort: Stylish 2BR for Long-Term Stays
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy a comfortable, fully equipped two-bedroom home designed for extended stays. Located in a walkable neighborhood clo ...
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Expedia
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VRBO
Wander & Wonder: A Hidden Gem in Portland’s Heart
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A beautifully furnished one-bedroom apartment designed for extended stays. Thoughtfully styled with modern finishes, a f ...
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VRBO
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Expedia
Spacious 3BR - Parking - W/D - 10 Min to Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Perfect for large groups, this setup combines two private apartments in the same building, offering six bedrooms, two ki ...
Click For Pricing
Expedia
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VRBO
Walkable near downtown 1 Bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A nautical themed 1 bedroom unit complete w/ legit ready to play DVD of Disney's "20,000 Leagues Under the Sea!" (full s ...
Click For Pricing
VRBO
From $330 per night (USD)
Expedia
Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of Downtown Portland
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
An elegant, sunny, first floor townhouse apartment on one of Portland's most beautiful, historic streets. With excellent ...
From $330 per night (USD)
Expedia
From $1036 per night (USD)
VRBO
Luxury Maine Living on Peaks Island at Water's Edge
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Water's Edge is a stunning newly built, 3 bedroom/3 bath modern home on Peaks Island Maine. Peaks is the closest islan ...
From $1036 per night (USD)
VRBO
From $173 per night (USD)
VRBO
Walk to Shops & Eats: Sleek Portland Studio!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Pet Friendly w/ Fee | Near I-295 | Remote Workers Welcome Tucked in a quiet Portland, ME, neighborhood, this single-sto ...
From $173 per night (USD)
VRBO
Click For Pricing
VRBO
Whale of a Time Summa
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Whale of a Time is a perennial favorite. Located in a quiet neighborhood within walking distance to the ferry b ...
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VRBO
From $493 per night (USD)
Expedia
Beautiful West End Apartment
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
All the comforts of home- 3 bedrooms and beautiful kitchen to share with family or friends. Close to town and walking di ...
From $493 per night (USD)
Expedia
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VRBO
City & Water View - Charming 2-bedrooom AC, WiFi - walking distance to Old Port
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Available on the week of July 4th. We are flexible on dates, contact us if you have specifics that aren't allowed by th ...
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VRBO
From $968 per night (USD)
VRBO
Sweeping Ocean Views in Cape Elizabeth Maine
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
See, smell, and hear the ocean from this 1901 fully renovated Cape Elizabeth cottage with sweeping water views throughou ...
From $968 per night (USD)
VRBO
From $671 per night (USD)
VRBO
Spacious Portland Home + Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Step into a piece of Portland history in this beautifully restored 3BR/2BA home, built in 1874 and updated with care ove ...
From $671 per night (USD)
VRBO
$Beautiful Back Cove Area/ \Maine the Way Life Should Be\$
From $171 per night (USD)
Expedia
Beautiful Back Cove Area/ \"Maine the Way Life Should Be\"
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
.*PLEASE READ ENTIRE DESCRIPTION* Back Cove a beautiful area with an ocean inlet has a 3.5 mile bike & walking path. ...
From $171 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Modern Getaway by the Sea
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect home away from home in beautiful South Portland, Maine! This modern and stylish 3-bedroom reside ...
From $581 per night (USD)
VRBO
From $790 per night (USD)
Expedia
Charming 3-bedroom townhome on Great Diamond Island in Portland, ME
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this modern townhome in picturesque Portland. This rental boasts 3 cozy bedrooms - one with a queen bed, anoth ...
From $790 per night (USD)
Expedia
From $554 per night (USD)
VRBO
Munjoy Hill Haus- Experience the best location in Portland
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Make yourself at home in this delightful 3-bedroom Portland retreat. With 2 queen beds and 1 bunk bed, this tranquil hou ...
From $554 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Elegant and efficient Island home 4 miles from downtown Portland
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A beautiful, elegant, and relaxing property on an island with all that Maine living should be, and only a 15 minute Fog ...
From $469 per night (USD)
Expedia
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VRBO
4-bedroom house steps from the beach in welcoming South Portland with AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience luxury coastal living at this fully furnished, renovated 4-bed (King, 2 queens, and 2 twin beds), 2-bath home ...
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VRBO
From $133 per night (USD)
Expedia
Willard Area Condo 2 Bedroom Walk to Beach 30 Day Min, Monthly Discount
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come home to the Willard Treehouse a sunny two-bedroom, one bath condo in a quiet section of the Willard Square and Beac ...
From $133 per night (USD)
Expedia
From $431 per night (USD)
VRBO
The 87th Townhome - Local Landmark Property
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Stay in historic elegance at 87 Pine Street, a charming landmark home in Portland’s sought-after West End. Enjoy spaciou ...
From $431 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Modern Coastal Retreat on Cottage Road
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your South Portland escape! This beautifully built 2-bedroom, 2-bathroom single-family home blends modern de ...
From $136 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
This is two units in one house connected by a laundry room! Host your whole crew here but give the in-laws or the kids t ...
From $415 per night (USD)
VRBO
From $266 per night (USD)
Expedia
Downtown Portland 2B2B Condo with Water View
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Downtown top-floor corner condo with water view. Furnished 2BR/2BA at the edge of Portland's Old Port. Enjoy water view ...
From $266 per night (USD)
Expedia
From $455 per night (USD)
VRBO
3BR Mid-Century Modern Retreat Near Portland & Willard Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
A stylish yet cozy retreat created by a writer-and-designer couple. Just minutes from Portland’s Old Port, beaches, and ...
From $455 per night (USD)
VRBO
Click For Pricing
Expedia
Bright Charming Victorian Close to Everything!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
35 E Kidder street is a turn of the century classic. It has historical charm matched with modern amenities. This unique ...
Click For Pricing
Expedia
From $323 per night (USD)
VRBO
Cozy Coveside Island Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Coveside Island Retreat | 2BR Duplex with Sauna & Pool Access Unplug and unwind at this cozy two-bedroom, one-and-a-hal ...
From $323 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Historic Island Retreat on Great Diamond Island with resort like amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay in the original Surgeon’s Quarters on Great Diamond Island! This 2BR/2BA historic brick home blends charming detail ...
From $535 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Winter rental - Bright and charming townhome atop Munjoy Hill. 11/1/25- 5/31/26
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This delightful two-story property offers two comfortable bedrooms with queen beds, a freshly updated bathroom with a ba ...
From $272 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Bright Charming Victorian Close to Everything!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
35 E Kidder street is a turn of the century classic. It has historical charm matched with modern amenities. This unique ...
From $339 per night (USD)
VRBO
From $690 per night (USD)
VRBO
Amazing Oceanfront Brand NewHome Ideal location - NEW LISTING DISCOUNT OFFERED!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
NEW LISTING DISCOUNT - The price listed reflects a 30% discount which is offered for any 2025 booking (2 day minimum) b ...
From $690 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Serene & Charming 2BR Guest Apartment – Near Trails & Downtown Portland
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Welcome to this enchanting apartment in Portland! This cozy 2-bedroom, 1-bath space offers the perfect mix of comfort an ...
From $246 per night (USD)
Expedia
From $3061 per night (USD)
VRBO
Charming, airy apt., steps from Eastern Promenade in lovely Portland with AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located in Portland in the Munjoy Hill Neighborhood, near the Old Port. Spacious and full of light, with everything you ...
From $3061 per night (USD)
VRBO
From $381 per night (USD)
Expedia
Chic 3-bedroom house in Munjoy Hill with off-street parking.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Centrally located within Portland's charming Munjoy Hill neighborhood, your home away from home is only a 5 minute walk ...
From $381 per night (USD)
Expedia
Click For Pricing
VRBO
Family Friendly Riverton Neighborhood Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Family-friendly comfort meets Portland convenience! This stylish 3BR/2BA home in the Riverton neighborhood sleeps 6 and ...
Click For Pricing
VRBO

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Portland Rentals

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Results: 377 Rentals