Portland Rentals
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Exquisite 2BR/2BA+Stunning Views+Munjoy Hill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This recently renovated two-family home with stunning views of the Fore River, marina, and Casco Bay shipping channel is ...
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From $334 per night (USD)VRBO
Peaks Cottage: Modern amenities, island charm, steps to shore
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Adorable almost new Peaks Island cottage. Three bedrooms, open kitchen, living area with awesome, comfortable window sea ...
From $334 per night (USD)VRBO
From $328 per night (USD)VRBO
Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Cozy home located in a very quiet and family friendly neighborhood at the end of a dead end street. Brookside has a larg ...
From $328 per night (USD)VRBO
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Maine Artist Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in one of Portlands historic Victorian mansards 1881 one block off the Casco Bay close to lighthouses, shopping, ai ...
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From $426 per night (USD)VRBO
Fresh East End Apartment Walkable to Downtown Portland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kick back on the glossy green Chesterfield at this sunlit, loft-style retreat in Munjoy Hill with open shelving bursting ...
From $426 per night (USD)VRBO
From $437 per night (USD)Expedia
Elegant condo - walk to Portland's best restaurants & Old Port
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A Foodie’s Delight Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $437 per night (USD)Expedia
From $164 per night (USD)VRBO
Cute 2+ Bedroom Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cute 2+ Bedroom Cottage. A short walk from the Ferry. Sleeps 6. Full Kitchen for your convenience. Picnic Table and ...
From $164 per night (USD)VRBO
From $894 per night (USD)VRBO
Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Cindy's Place is a hidden gem located on the rocky shoreline of Peaks Island overlooking the Casco Bay and the Portland ...
From $894 per night (USD)VRBO
From $413 per night (USD)VRBO
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Pearl of Portland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $413 per night (USD)VRBO
From $545 per night (USD)Expedia
Large, light filled 4 bedroom house - walk to ocean and ferry
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Heron's Perch on Peaks' Island has space to hold everyone and cozy spots to curl up on your own. Just steps to the marke ...
From $545 per night (USD)Expedia
From $297 per night (USD)VRBO
Willard Beach Get Away - Dog Friendly - Steps from the shore!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Perfect for a Maine summer vacation. This 400 sq foot studio apartment is one house away from Willard Beach, 4 blocks t ...
From $297 per night (USD)VRBO
From $248 per night (USD)Expedia
West End 2nd Floor Apartment 762 Congress Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Regards, Brad 203-258-1301 C762CongressStreet@yahoo.com This is a furnished second-floor apartment located at 762 Congr ...
From $248 per night (USD)Expedia
From $609 per night (USD)VRBO
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
We close up the cottage during the winter months. Available May 1 - Columbus Day. One-week minimum, Saturday - Saturday ...
From $609 per night (USD)VRBO
From $340 per night (USD)Expedia
Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Just renovated 4 bedroom off of Back Cove Portland. Sunny, bright and open plan. Great common areas for family or reunio ...
From $340 per night (USD)Expedia
From $367 per night (USD)VRBO
Hollywood meets seaside charm in the former cottage of famed director, John Ford
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
You'll feel you've got one foot in the present and the other in the past when you step over the threshold of this sweet, ...
From $367 per night (USD)VRBO
From $313 per night (USD)VRBO
Stunning White Water Ocean Views From This Peaks Island Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escaping to Valhalla by the Sea is like escaping to a simpler time, an experience not marked by time, but by your spirit ...
From $313 per night (USD)VRBO
From $173 per night (USD)VRBO
Urban studio in an amazing, central location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location, location! And of the best locations in town! This is such a great place to stay while in Portland. I have no d ...
From $173 per night (USD)VRBO
From $798 per night (USD)Expedia
Upscale large 3 bedroom unit within walking distance to everything!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Designer inspired spacious, modern home where detailed patterns and vibrant colors intertwine to create a space that fee ...
From $798 per night (USD)Expedia
From $1993 per night (USD)VRBO
Art Filled East End Home a short walk to waterfront, restaurants and shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Exquisitely decorated, art-filled home on Portland's highly sought after East End. Stunning water views from the master ...
From $1993 per night (USD)VRBO
From $278 per night (USD)VRBO
Classic Island Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious, charming 1896 cottage at the top of quiet, magical footpath. Has a secluded, peaceful feel but is only a 2-3 ...
From $278 per night (USD)VRBO
From $230 per night (USD)VRBO
Charming Peaks Island Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
City of Portland license # STHR 000153 2021 2021 updates: New queen memory foam mattress , new large shower, new Rinn ...
From $230 per night (USD)VRBO
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Luxury Modern Home with a View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the good life in this elegant and bold modern home on Portland’s coveted Munjoy Hill. Newly constructed and d ...
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From $787 per night (USD)VRBO
The best place for the money!!!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Heart of the West End, which is on the peninsula and part of the downtown. Quiet neighborhood, but nice bars and restaur ...
From $787 per night (USD)VRBO
From $332 per night (USD)VRBO
Charming, Secluded, Island Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming, Secluded, Island Getaway for family and friends! This Down-front getaway has all the advantages to make your ...
From $332 per night (USD)VRBO
From $273 per night (USD)VRBO
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom Townhouse Style Unit Welcome to 255 Spring Street, Unit #10! Historic and lovingly maintained West End prope ...
From $273 per night (USD)VRBO
From $568 per night (USD)VRBO
Classic Turn of the Century Island Summer Cottage
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 8
'Evergreen Anchorage' has had many roles over the last century- a 1920's guest house, a tea room and an antique store. O ...
From $568 per night (USD)VRBO
From $241 per night (USD)VRBO
Charming Craftsman Retreat- 5 minute walk to Willard Beach- 30 night minimum
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***We DO NOT list this house on Craigslist. The Angell House, located in the Willard Square area of South Portland, sit ...
From $241 per night (USD)VRBO
From $445 per night (USD)VRBO
Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Available May 1 - Columbus Day. Full-week rentals only, Saturday-Saturday July 1 - Labor Day. Three-day minimum otherwis ...
From $445 per night (USD)VRBO
From $916 per night (USD)VRBO
Bright, spacious home, new kitchen, hot tub, beautiful art, EV charger
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get away to a comfortable, spacious and bright home in a quiet neighborhood with a brand new, gorgeous kitchen. A heat p ...
From $916 per night (USD)VRBO
From $270 per night (USD)VRBO
Quiet, residential neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This studio suite can sleep 2 to 4 people, is newly built, with a complete kitchen, washer/dryer, air-conditioning, cabl ...
From $270 per night (USD)VRBO
From $385 per night (USD)VRBO
Sunny, modern, family home w large yard. Summer on beautiful Peaks Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Last minute cancellation - August 17 to 24. Full week or partial (4 day minimum). Full week is discounted to $250/night, ...
From $385 per night (USD)VRBO
From $294 per night (USD)Expedia
Spacious and Modern One Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Modern 1st floor one bedroom apartment in a walk up apt building which has been recently fully renovated. The apartment ...
From $294 per night (USD)Expedia
From $405 per night (USD)VRBO
Brand new single family Munjoy Hill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunny, art filled, new single family on Munjoy Hill. This home has been totally renovated with it’s sunny new kitchen, l ...
From $405 per night (USD)VRBO
From $362 per night (USD)VRBO
Spacious Historic 1st Floor Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
This is a charming art deco home built in 1915. The property has been recently renovated. There are many quirks of an ol ...
From $362 per night (USD)VRBO
From $1587 per night (USD)VRBO
PORTLAND PENINSULA-SPACIOUS WALKABLE EAST END SPOT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 12
You will not find a more ideal location for your stay In Portland! Beautifully renovated and designed with all of the am ...
From $1587 per night (USD)VRBO
From $541 per night (USD)VRBO
Charming Great Diamond Island Cottage w/Waterviews - Bus. Lic.# STHR-003849-2021
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This quintessential Maine cottage on Great Diamond Island is as charming as it gets. You get the best of all worlds here ...
From $541 per night (USD)VRBO
From $403 per night (USD)VRBO
City Amenities, Casco Bay Sunrises and Natural Beauty
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Martin's Point high end home. This is a unique space that includes a beautiful view of Casco Bay with a waterfront park ...
From $403 per night (USD)VRBO
From $646 per night (USD)Expedia
The Monument Garden SWEET!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
We call this first floor of our modified 1890`s Victorian the `Garden SWEET` because it`s a huge suite that is so attrac ...
From $646 per night (USD)Expedia
From $357 per night (USD)VRBO
Classic turn of the century Maine cottage
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Come experience Maine island living in this beautifully preserved turn of the century home. Libby Cottage is located in ...
From $357 per night (USD)VRBO
From $1737 per night (USD)VRBO
Stunning Entire Three Units Apts (USM AREA)
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 22
This 4200 sq.ft newly renovated entire three units apartments are located in a quiet Oakdale neighborhood, short walk to ...
From $1737 per night (USD)VRBO
From $453 per night (USD)VRBO
Completely remodeled 2 bedroom apartment in Portland's West End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come stay in this brand new 2 bedroom 1.5 bath apartment in the heart of Portland's West End. Located just steps away f ...
From $453 per night (USD)VRBO
From $341 per night (USD)Expedia
Cozy, Elegant and Bright 2 bed in the East End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy and elegant 2 bed apartment in Portland’s East End. Whether you want to walk into town for dinner or sample the loc ...
From $341 per night (USD)Expedia
From $615 per night (USD)VRBO
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Panoramic Oceanfront and island view direct sunrise. Nature preserves and hiking trail next door and nearby. Away from ...
From $615 per night (USD)VRBO
From $1343 per night (USD)VRBO
Private Oceanfront Island Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 20
Beautiful private oceanfront property on Long Island, ME! This property has 3 buildings: the main house, the stand alo ...
From $1343 per night (USD)VRBO
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Eclectic condo in charming West End
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Charming, eclectic condo in West End. Quiet and private. Host lives next door in separate quarters. Onsite parking. Baby ...
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From $437 per night (USD)Expedia
Back yard paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Wake up to the sounds of chickadees (Maine’s state bird), you sip your coffee in this furnished family home. With except ...
From $437 per night (USD)Expedia
From $125 per night (USD)VRBO
Back Cove Charmer Close to Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunny Fresh Newly Renovated 1 Bedroom Apt w/Queen (and separate "full" size pullout couch in living room). Well appointe ...
From $125 per night (USD)VRBO
From $491 per night (USD)Expedia
Newly Renovated 2nd Floor Apt near USM
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This gorgeous apartment features 3 bedrooms plus a bonus room off master bedroom, one with king size bed, two queen size ...
From $491 per night (USD)Expedia
From $408 per night (USD)VRBO
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spacious, elegant new construction, 1 BR apartment, includes full kitchen with washer/dryer, spa like bathroom with plus ...
From $408 per night (USD)VRBO
From $314 per night (USD)Expedia
Chic One Bedroom Apartment In Portland's Arts District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautifully furnished one bedroom apartment for 2 is on the first floor of a historic 1890 building. Completely re ...
From $314 per night (USD)Expedia
From $203 per night (USD)VRBO
Water View Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Street View and Google are not updated, this home and neighboring homes have been recently renovated, fully furnished ho ...
From $203 per night (USD)VRBO
From $245 per night (USD)Expedia
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy spacious accommodations and two floor living with 1200 square feet of living space. Walk to the local markets and ...
From $245 per night (USD)Expedia
From $1091 per night (USD)VRBO
Superb Location!! Heart of Old Port/Spacious Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Come explore the beautiful, historic and vibrant Old Port District when you stay at this stunning walk-up loft apartment ...
From $1091 per night (USD)VRBO
From $407 per night (USD)Expedia
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cumberland Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $407 per night (USD)Expedia
From $458 per night (USD)VRBO
2 Bedroom Apartment on Top Floor in Portland's West End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come stay in the heart of Portland's West End. Located just steps away from some of the best restaurants, cafes and bars ...
From $458 per night (USD)VRBO
From $710 per night (USD)Expedia
416 Fore St Apartment 2
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the heart of the Old Port! A gem located in the middle of this historic district. Features 3 bedrooms, luxe l ...
From $710 per night (USD)Expedia
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Coastal Home 2 blocks from beach (hot/dry sauna)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New listing! Our home is a 3 Bedroom, 2.5 bath beautiful and contemporary colonial home located in the hip, coastal Will ...
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From $506 per night (USD)Expedia
Spectacular 3rd Floor Apt Near Downtown Portland
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This 1,400 sq.ft newly renovated third floor apartment is located in a quiet Oakdale neighborhood, short walk to Back Co ...
From $506 per night (USD)Expedia
From $1074 per night (USD)VRBO
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to your home away from home in Portland, Maine! This charming six-bedroom, three-bath Craftsman-style house offe ...
From $1074 per night (USD)VRBO
From $234 per night (USD)Expedia
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy spacious accommodations and two floor living with 1200 square feet of living space. Amenities Include a well equip ...
From $234 per night (USD)Expedia
From $335 per night (USD)VRBO
Victorian architecture dipped in refined modernity. May-June-July special!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Aged and sturdy, yet eminently modernized, this two bedroom boutique loft is perfectly situated in the heart of Portland ...
From $335 per night (USD)VRBO
From $404 per night (USD)Expedia
The perfect refinement of vintage seduction. May-June-July special!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This recently remodeled open-plan living area is spacious in size and flooded with natural daylight that bounces off the ...
From $404 per night (USD)Expedia
From $164 per night (USD)VRBO
Ultra cool new modern flat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
“This is the best basement apartment I have seen, wow!" This historic unique one of a kind 1600sqft boutique basement a ...
From $164 per night (USD)VRBO
From $1000 per night (USD)Expedia
Stylish & Spacious Townhouse w/Garden, Family-friendly, walk to downtown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our light-filled three story home is perched on a lovely, quiet corner of the historic West End residential neighborhood ...
From $1000 per night (USD)Expedia
From $565 per night (USD)VRBO
Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summer 7 day minimm (otherwise 2 night min except 3-5 nights for holidays) Gather with loved ones at Selkies' Rest: Coz ...
From $565 per night (USD)VRBO
From $370 per night (USD)Expedia
Brand New 1 Bedroom Apartment in Portland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come and enjoy this fully remodeled 1 bedroom apartment located on the 2nd floor of a historic brownstone row house in P ...
From $370 per night (USD)Expedia
From $304 per night (USD)VRBO
Convenient Portland home 3 miles from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
A "Great Escape" awaits you at this gorgeous Portland gem! This perfect Maine get away sits in a quiet residential neigh ...
From $304 per night (USD)VRBO
From $383 per night (USD)Expedia
Nature with in-town living that feels a world away. May-June-July special!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse in the tranquility of nature while allowing your comfort be seduced by this architect's successful attempt at a ...
From $383 per night (USD)Expedia
From $671 per night (USD)VRBO
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bella Vista is a 3 bedroom, 2 1/2 bath home sitting directly on the Atlantic Ocean side of Peaks Island at Elm Tree Co ...
From $671 per night (USD)VRBO
From $499 per night (USD)VRBO
Luxurious 2 Bedroom Loft in Portland’s Art District
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stylishly decorated art loft walkable to the PMA and all live performance venues: Aura, Cross Arena, Merrill, Portland S ...
From $499 per night (USD)VRBO
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Entire Home with Yard Close to it All
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3BR plus large Livingroom with pullout, 2BA, bar, workspace, washer/dryer, porch, yard, BBQ, fire pit, walkable to east ...
Click For PricingVRBO
From $305 per night (USD)VRBO
Arlie's Digs! - One Block To Willard Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Ground-floor, updated, 2-bdr condo in an historic 150-yr-old bldg. in the heart of Willard Square- steps from Portland ' ...
From $305 per night (USD)VRBO
From $466 per night (USD)VRBO
Panoramic views of Casco Bay, spacious and modern single family home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<b>Welcome to Vacationland! <b><p> <p> This spacious, fully updated single family home is the perfect location for seein ...
From $466 per night (USD)VRBO
From $435 per night (USD)VRBO
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come experience a bit of history in this 1200 sq ft , circa 1870 cottage with charming original features and modern con ...
From $435 per night (USD)VRBO
From $365 per night (USD)VRBO
Great 2 bedroom apartment on Munjoy Hill! Private backyard - walk everywhere!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful 2 bedroom, sunny, modern apartment. Deck with gorgeous view of Casco Bay. Private,peaceful, beautiful yard w ...
From $365 per night (USD)VRBO
From $665 per night (USD)Expedia
Wonderful Portland Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wonderful cottage style home with spectacular views and direct access to your own waterfront. Perfect for kayaking, SUP ...
From $665 per night (USD)Expedia
From $518 per night (USD)VRBO
Peaks Island Cottage with beautiful view of Whitehead passage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This well appointed seasonal cottage has everything you need to enjoy your family vacation on one of Casco Bay’s calenda ...
From $518 per night (USD)VRBO
From $462 per night (USD)Expedia
Amazing Ocean View Summer Cottage Rental w/ Boat Mooring on Great Diamond Island
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Vacation summer house on Great Diamond Island, with a boat mooring. Our 4 bedroom house sports a grand view of Casco Ba ...
From $462 per night (USD)Expedia
From $408 per night (USD)VRBO
Bright & Spacious Apartment with Amazing Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Spend your vacation, work-trip, or weekend getaway in our lovely, downtown apartment. Apartment 3 is located on the thir ...
From $408 per night (USD)VRBO
From $372 per night (USD)Expedia
Panoramic Water, Island & City Views w/Private Roof Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We call our beautiful 3rd floor apartment ‘The Crow’s Nest’ not only because of the circular staircase that leads up to ...
From $372 per night (USD)Expedia
From $634 per night (USD)VRBO
The Monument SWEET Life
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Registration #2018-4090. Walk everywhere from the SWEET! This huge, beautifully furnished space w/4 full bedrooms, plu ...
From $634 per night (USD)VRBO
From $433 per night (USD)Expedia
Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Windows with massive water & city views from the kitchen, dining and living areas, and 360 degrees from your private roo ...
From $433 per night (USD)Expedia
From $512 per night (USD)VRBO
Beautiful 1st Floor Apartment & Amazing Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Portland, ME, the secret vacation destination that is no longer a secret. Come stay with us and enjoy the ent ...
From $512 per night (USD)VRBO
From $146 per night (USD)Expedia
Rent a room in the gorgeous Holt House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a private room in the gorgeous Holt House and bask in the ornate mixed designs of John Calvin Stevens, one of Ameri ...
From $146 per night (USD)Expedia
From $646 per night (USD)VRBO
Luxury King Room with Parlor and Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located on Maine's Great Diamond Island, the Inn at Diamond Cove is a tranquil destination that provides guests with a p ...
From $646 per night (USD)VRBO
From $680 per night (USD)Expedia
King Suite with Kitchenette & Balcony on Great Diamond Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located on Maine's Great Diamond Island, the Inn at Diamond Cove is a tranquil destination that provides guests with a p ...
From $680 per night (USD)Expedia
From $143 per night (USD)VRBO
Rent a room in the gorgeous Holt House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rent a private room in the gorgeous Holt House and bask in the ornate mixed designs of John Calvin Stevens, one of Ameri ...
From $143 per night (USD)VRBO
From $595 per night (USD)Expedia
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our Greek Revival home, built in 1875, combines beautiful historic details with modern updates to create a cozy and ecle ...
From $595 per night (USD)Expedia
From $683 per night (USD)VRBO
Downtown Penthouse Suite - Stunning Harbor Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20182242-ST Private 1850's Old Port Penthouse w/Breathtaking Views and Complimentar ...
From $683 per night (USD)VRBO
From $876 per night (USD)Expedia
Penthouse Two Master Waterfront Suite with Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20185280-ST Stunning penthouse suite with exposed beams, brick accents, and whitewa ...
From $876 per night (USD)Expedia
From $847 per night (USD)VRBO
Distinguished classic coastal home overlooks Casco Bay and Maine’s rocky shore!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Classic colonial overlooking Casco Bay and Maine’s rocky shore. This beautiful coastal home is located at the highest po ...
From $847 per night (USD)VRBO
From $903 per night (USD)Expedia
Waterfront Two Master Suite Penthouse with Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar wal ...
From $903 per night (USD)Expedia
From $717 per night (USD)VRBO
Old Port Penthouse Suite - Amazing Harbor Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quie ...
From $717 per night (USD)VRBO
From $258 per night (USD)VRBO
Sweet Island Cottage- 3 minute walk to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
To See It is to Love It! A sweet island cottage with everything you need for a home away from home. Private bedroom with ...
From $258 per night (USD)VRBO
From $567 per night (USD)VRBO
Modern West End 2 Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
You will not be disappointed in this Modern 2 bedroom apartment walk-in 1st floor unit able to comfortably accommodate ...
From $567 per night (USD)VRBO
From $464 per night (USD)VRBO
Ocean front cottage with private beach.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful Maine cottage with extra large porch with rocking chairs and 200 degree views of Casco Bay. Charming 2 bedroom ...
From $464 per night (USD)VRBO
From $342 per night (USD)VRBO
The Globe House on Munjoy Hill - Walk to Breweries
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A fun, modern, cozy apartment sitting on top of Munjoy Hill on North Street. Enjoy some of the best views in the city fa ...
From $342 per night (USD)VRBO
From $212 per night (USD)Expedia
LIVE LIKE A LOCAL // HIP & HISTORIC OLD PORT CHARM
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local! Be in the middle of everything with award winning restaurants, bakeries, coffee shops, breweries, ind ...
From $212 per night (USD)Expedia
From $359 per night (USD)VRBO
Brand New 2 Bedroom Apartment in Heart of West End
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come and enjoy this fully remodeled 2 bedroom apartment located on the first floor of a historic brownstone row house in ...
From $359 per night (USD)VRBO
From $311 per night (USD)VRBO
Private setting for a couple-just two people in the whole house!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Glorious Long Island Maine! Quiet, peaceful, friendly neighbors. Looking for a place to relax and rekindle your romanc ...
From $311 per night (USD)VRBO