Vacation Home Rentals By Owner In Portland, ME

$644.27

Entire House Deering Highlands

Portland, Maine, United States

Welcome to Your Portland Paradise!brbrbrbrNestled in the heart of Portland, this house blends historic charm with modern comforts.brbrbrbrEnjoy natural light pouring in from all directions on both floors.brbrbrbrFully stocked kitchen with everything you need to whip up delicious meals.brbrbrbrFlat screen TV and two sound systems.brbrbrbrFast internet to keep you plugged in.brbrbrbrSunny South-Facing Deck: Bask in full sunlight from dawn till dusk.brbrbrbrLicense Number: STHR-006224-2024

3

Bed

2

Bath

6

Sleeps

$630.34

/ Nightly

Private Vacation Home

A Spacious and Charming Island Townhome

Portland, Maine, United States

This private end-unit townhome on Great Diamond Island offers a peaceful retreat with front and back porches. The open-concept kitchen flows into the living area, creating a welcoming space for guests. A short walk or bike ride leads to beaches, dining, and the ferry.brbrGreat Diamond Island in Casco Bay, off the coast of Portland, is one of the most picturesque islands in Maine.brbrVisitors come via ferry, water taxi, or private boat to explore this secluded jewel and take in the island's 193 acres of spectacular natural landscape perfect for outdoor recreation and relaxation.brDiamond Cove is the island's small private residential community, formerly a military base built during America's Gilded Age. Army structures that were once scattered over the land have been restored and are now homes with wonderful historic detail and character.brbrPrior to being an army base, Diamond Cove was a famous artists' retreat where American literary greats such as Henry Wadsworth Longfellow and Harriet Beecher Stowe spent time.brbrToday, Diamond Cove is also home to the luxurious Inn at Diamond Cove, highly rated Diamonds Edge Restaurant, and the Fort McKinley Museum.brbrWith its spectacular sunsets, sheltered beaches, and acres of old-growth forest, this unique and historic location offers visitors an unparalleled opportunity to experience the tranquility of Maine island living.brbrGreat Diamond Island is not ACCessible from the mainland by car and the primary modes of transportation are golf carts and bicycles.brbrCommunity Amenities include:brDuckpin bowlingbrFitness gymbrGame roombrIndoor basketball courtbrLibrarybrMailroombrPrivate beachesbrSwimming poolbrTennis courtsbrWalking trailsbrbrGETTING HEREbrDiamond Cove is a car-free community, which is part of what makes it so special. Parking in Portland is the sole responsibility of the guest. Guests must arrive on the Diamond Cove Dock via Ferry or Water Taxi. This is part of the magical experience of entering the Island State of Mind. brbrPRIVATE WATER TAXIbrWe highly suggest arranging a private water taxi before your arrival. We recommend contacting Fogg’s Water Taxi Service.brbrFERRYbrAnother method of transportation is the Ferry service, provided by Casco Bay Lines. The ferry terminal is located at the Maine State Pier, 56 Commercial Street, Portland, ME. While we are located on Great Diamond Island, please ensure you are purchasing tickets to the Diamond Cove Dock. The most updated schedule is on the Casco Bay Lines website.

Bed

Bath

Sleeps

$438.21

/ Nightly

Private Vacation Home

Nature with in-town living that feels a world away. May-June-July special!!!

Portland, Maine, United States

Immerse in the tranquility of nature while allowing your comfort be seduced by this architect's successful attempt at a one of a kind custom New England cottage. Less than two minutes away from the airport and less than 6 minutes from downtown, this private neighborhood on the river offers all the right mix of outdoorsy adventure, quiet and convenient logistics.brbrThe spacebrTwo kayaks available for river exploration upon demand.brbrGuest accessbrbrIt is self check in. Access details will be provided on the day of arrival.brbrYou also have a designated parking spot during your stay provided on the day of arrival.brbrRiver, bike/walking trail on StroudwaterbrbrNeighborhood overviewbr3 mile bike trail a minute away. brRiver adventure a minute away. brRide to the airport a minute away. brRide to downtown 6 minutes away (with traffic). brFreeway 95 is 3 minutes away. brFreeway 295 is 4 minutes away. brConvenient proximity to downtown's restaurants, shops and bars.brbrThere is a basement section independent and cut off/segregated from the main house (with noise cancellation) not included as part of the rental. It may be sometimes occupied by owner. It has its separate entry and exit.br

3

Bed

2

Bath

6

Sleeps

$738.2

/ Nightly

Private Vacation Home

Spacious Historic Home on Diamond Cove

Portland, Maine, United States

The great room features a large fireplaces creating a warm and inviting space. The first floor offers a modern kitchen, den, and two bedrooms, while the second level includes two bedroom suites. Outside, enjoy the expansive patio, mature grounds, and historic brick stack. A unique blend of history and modern comfort.brbrGreat Diamond Island in Casco Bay, off the coast of Portland, is one of the most picturesque islands in Maine.brbrVisitors come via ferry, water taxi, or private boat to explore this secluded jewel and take in the island's 193 acres of spectacular natural landscape perfect for outdoor recreation and relaxation.brDiamond Cove is the island's small private residential community, formerly a military base built during America's Gilded Age. Army structures that were once scattered over the land have been restored and are now homes with wonderful historic detail and character.brbrPrior to being an army base, Diamond Cove was a famous artists' retreat where American literary greats such as Henry Wadsworth Longfellow and Harriet Beecher Stowe spent time.brToday, Diamond Cove is also home to the luxurious Inn at Diamond Cove, highly rated Diamonds Edge Restaurant, and the Fort McKinley Museum.brbrWith its spectacular sunsets, sheltered beaches, and acres of old-growth forest, this unique and historic location offers visitors an unparalleled opportunity to experience the tranquility of Maine island living.brbrGreat Diamond Island is not accessible from the mainland by car and the primary modes of transportation are golf carts and bicycles.brbrCommunity Amenities include:brDuckpin bowlingbrFitness gymbrGame roombrIndoor basketball courtbrLibrarybrMailroombrPrivate beachesbrSwimming poolbrTennis courtsbrWalking trailsbrbrGETTING HEREbrDiamond Cove is a car-free community, which is part of what makes it so special. Parking in Portland is the sole responsibility of the guest. Guests must arrive on the Diamond Cove Dock via Ferry or Water Taxi. This is part of the magical experience of entering the Island State of Mind. brbrPRIVATE WATER TAXIbrWe highly suggest arranging a private water taxi before your arrival. We recommend contacting Fogg’s Water Taxi Service.brbrFERRYbrAnother method of transportation is the Ferry service, provided by Casco Bay Lines. The ferry terminal is located at the Maine State Pier, 56 Commercial Street, Portland, ME. While we are located on Great Diamond Island, please ensure you are purchasing tickets to the Diamond Cove Dock. The most updated schedule is on the Casco Bay Lines website.

4

Bed

4

Bath

8

Sleeps

$816.41

/ Nightly

Private Vacation Home

Sunny future conscious home in Portland

Portland, Maine, United States

This gorgeous family home, recently built in 2019, provides the perfect balance of outdoor relaxation and proximity to popular Portland attractions. Highlights include a Tesla EV charger, dishwasher, washer & dryer, hammock, stone fire pit, grill, outdoor dining furniture, 3 driveway parking spaces, dual shower heads, bidet, towel warmer, heat pumps with AC, ventilation system & dimmable lights throughout- all only 600 feet from Back Cove!brbrCLEAN COOL AIR:brPlenty of fresh air being circulated with our newly installed ERV (ventilation) system and heat pumps on each floor (for heating and cooling). Guests can boost the ERV (ventilation) with buttons in each bathroom. There are also ceiling fans throughout the home. brbrSOUND SYSTEM:brA Sonos sound system is also available throughout the house with three different zones. (Guests can connect directly through our Wifi to Airplay your favorite music.)brbrBACKYARD:brFenced in backyard includes a stone fire pit area with Adirondack chairs, hammock, and surrounding gardens. Stairs lead from the fire pit area to the deck where you'll find the grill & outdoor dining set with an umbrella for shade. (Grilling tools & propane tank provided)brbrOff-street parking available for 3 vehicles, along with a Tesla EV charger.brbrMAIN FLOOR:brThe main floor of our home is an open layout with the kitchen, dining area, living room & half bath. brbrFull kitchen boasts an induction stovetop, convection oven, dishwasher, family size refrigerator & freezer with an ice maker, microwave, toaster, blender, drip coffee maker & tea kettle. Cooking basics including spices, oil, pots, pans, dishes and utensils all provided. Cookware with utensils for lobster & clambakes also included. (This is our home 10 months out of the year, so there are many kitchen supplies for you to utilize, as well as pantry space for food storage.) We also participate in Portland's composting program, and have recycling bins you are welcome to utilize during your stay. Plenty of seating with a dining room table for 8, as well as additional island seating for 4.brbrThe living room on the main floor opens to the outside deck & backyard area. brbrSECOND FLOOR:brMaster bedroom includes a queen bed, ceiling fan, walk-in closet & dresser for plenty of clothing storage. brbrEnjoy the master bathroom double shower, with three shower heads (one rain shower, a secondary handheld, and a third fixed shower head on the other side!) Bidet, heated floors and a towel warmer are also included in this private bathroom.brbrIn the second bedroom on this floor you'll find another queen bed, with a memory foam mattress, closet & dresser. This bedroom has a reading nook, ceiling fan and allows a glimpse of the ocean on Back Bay Cove.brbrAnother full bathroom is located next to this bedroom & contains heated floors, a shower and bathtub. brbrWe provide all linens & towels, as well as extra pillows and blankets.brbrDOWNSTAIRS:brThe family room downstairs includes a 55 TV and access to Disney Plus & Hulu content. Other apps are available with your own sign-in. Tons of board games & reading materials for all ages throughout our home. Comfy couches in both living spaces. (Note: Guests will not be permitted to utilize the wood stove in the family room.)brbrThe laundry room contains a large capacity washer & dryer, as well as a utility sink for your use.brbrA third bedroom with a queen bed is off of the family room, which is also a private work area with desk space & high speed fiber internet for all of your professional needs. brbrWe also have a queen size air mattress (self-inflating) available upon request.brbrLicense # STHR-006847-2025brbrReviews:brOur group thoroughly enjoyed our stay here! The house is spotless and so comfortable (we had 8 people). The neighborhood is quiet, and so close to the Old Port/local attractions. I would highly recommend this home as a place to stay if you’re exploring the Portland area! -Rachael, July 2025brbrWe loved everything about staying at this location. It was close to the Back Cove for walking and beautiful views and we were able to walk for ice cream in the evening. The house is updated with a beautiful large kitchen and very comfortable rooms. Neighborhood was peaceful and a short drive to downtown Portland. -Rosalie, June 2025brbrVisited Maine for the first time with kids and their grandparents coming from North Carolina. Arian's place was very clean, had comfortable bedding, kitchen was well stocked with pots and pans for us to prepare some of our meals. The grocery store was very close, we enjoyed the location, a short drive to the Old port, harbor and beautiful lighthouses. Arian also has a good collection of books to relax after an exhausting day. Highly recommend this place for large families/groups. -Nanda, July 2025

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Bath

Sleeps

$792.4

/ Nightly

Private Vacation Home

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Portland, Maine, United States

brBella Vista is a 3 bedroom, 2 1/2 bath home sitting directly on the Atlantic Ocean side of Peaks Island at Elm Tree Cove. One of only 2 houses on a small dirt road abutting a land preserve and conservation land. See and hear the ocean waves crash into the rocks just outside of your living room and bedroom windows. Spectacular views from every room. Enjoy your morning coffee on the large covered porch with an unobstructed view of the sunrise and a panoramic view up and down the rocky coastline.. Absolutely breathtaking! One of the best spots on the backshore.brbrThe home is a well maintained cottage home with 3 bedrooms. All are tastefully decorated, and all have ocean views!!!.brbrThe 1st floor has a well stocked updated kitchen with good size refrigerator and an electric stove/oven and microwave. There is also a long L shaped dining/living room designed to take full advantage of the amazing view. There is also a library and a full bath with a shower on the 1st floor.brbrThe 2nd floor has 3 bedrooms: the 1st with a queen size bed and a half bath attached. The 2nd has a a full size bed and a futon. The 3rd has a twin and an Antique bed (small full - 48x72). There is also full bath with a shower/Jacuzzi tub.br brPeaks island is a 15 minute ferry from Portland, where you can experience a beautiful seaside town with a wide variety of great restaurants and activities. The island offers exceptional walking, jogging, horse riding, tennis, swimming and relaxing with a wild bird preserve, a social club for activities, little shops, grocery store and restaurants. You can easily walk to everything.brbrAmenities: wifi, weber gas grill, 42 flat panel LCD TV, cable TV, microwave, full-size oven range, toaster, Drip coffee-maker, Keurig coffee maker, all cooking and baking utensils you would need including a lobster pot, fire extinguisher and smoke detectors, washer/dryer, parking for 2 cars.brbrThings you'll find stocked at the cottage: propane for the gas grill, bedspreads and pillows (BATH TOWELS, BLANKETS AND LINENS ARE NOT INCLUDED, BUT ARE AVAILABLE FOR RENT - see below)*, the tools to make a lobster dinner, cleaning supplies, full set of dinnerware, cups, mugs, etc., grill tools, family games.brbrWeek long bookings are Sat - Sat. Between June 15 and Sept 15 WEEKLY BOOKINGS ONLY!!! Weekends considered between those dates if within 1 month of start of occupancy. Inquire of Owner (rates for on peak weekends if approved may be different than posted rate).brbrDogs are welcome.brbr*LINENS: If you wish to rent linens, please let me know They are available through our cleaning service. We do not mark up the price, but just offer this as a service for our guests: The rates are for the duration of your stay: flat rate of $160 for all beds and 8 towel sets (face, hand and bath). brbrThese prices are cheaper than local rentals and the beds will be made before your stay and stripped for you, so there is nothing for you to do.brbr brWe have another property nearby, a 60 second walk, please check it outbrVRBO # 1244485!brbror cut and paste following link in browserbrbrhttps://www.vrbo.com/1244485 utm_source=direct&utm_medium=social&utm_campaign=earned:vrbo:sharecopylink:USA&utm_content=1244485

Bed

Bath

Sleeps

$470.18

/ Nightly

Private Vacation Home

Bright Charming Victorian Close to Everything!

Portland, Maine, United States

35 E Kidder street is a turn of the century classic. It has historical charm matched with modern amenities. This unique house sits back away from the street protected by a large picket fenced front yard. It features stained glass windows, a covered porch, beautiful gardens and towering maple trees. Eastern facing tall windows provide excellent natural light both upstairs and down. The house is full of unique architectural details including built in bookshelves and hardwood floors throughout.brbrThe spacebrFirst Floor Features:br- The living room is both cozy and spacious with a large 55 flat screen perfect for curling up and streaming all of your favorite movies and shows with wifi and apple tv included.br- The dining room is surrounded by builtin bookshelves and contains a curated library for any reader as well as a large dinner table to host friends and family.br- The kitchen is very well equipped for any level of cook and features stainless steel appliances, butcher block countertops, an exterior vented range hood and a large farm sink.brbrSecond Floor Features:br- The staircase features a red and blue stained glass window that allows natural light to illuminate the space.br- There are two spacious bedrooms with queen beds, memory foam mattresses, crisp linens and new pillows. Each bedroom has its own closet and plenty of storage.br- The bathroom is bright, clean and warm with a bathtub shower and skylight. A linen closet in the hall provides excellent storage for fluffy towels and extra toiletries. A bonus feature is a very effective vent fan which also doubles as a bluetooth speaker and allows you to play music or catch up on podcasts while you get ready for the day.br- Upstairs you will also find an office that can easily double as a third bedroom. It features a private workspace with a desk and a large pullout couch for extra sleeping or just a comfy place to relax away from the rest of the house.brbrThis house includes all the conveniences of home including a slate tiled entry way to store boots and coats in the winter and a full size washer and dryer in the basement. The driveway also provides off street parking for up to two vehicles.brCome enjoy 35 East Kidder street and find your new home away from home and all the comfort and privacy that it provides.

Bed

Bath

Sleeps

$437.64

/ Nightly

Private Vacation Home

Sunny Modern Oasis in Portland’s Trendy East End

Portland, Maine, United States

Escape to this brand new modern space with views of the back cove and skyline. Walk to award winning restaurants, one of the five breweries and the beach. Explore trails overlooking bold open ocean with stops at the marina or the Old Port for retail therapy. Apartment features floor to ceiling windows, terrace and washer/dryer. 2 night minimum.

Bed

Bath

Sleeps

$608.07

/ Nightly

Private Vacation Home

Oceanfront Property on Backshore of Peaks Island, Maine, Sleeps 8

Portland, Maine, United States

Heaven on Earth - Welcome to The House at Table Rock. Only steps from the open ocean with over an acre of property on Peaks Island, Maine, The House at Table Rock is situated between Table Rock and Spar Cove with expansive Atlantic Ocean views. Surrounded by wildflowers and sea roses, the House at Table Rock is a perfect place to gather friends and family for the vacation of a lifetime where Island-time is your time. House at Table Rock includes a beautiful expansive living room and dining room designed to marvel at the extraordinary sunrises and sunsets over the open ocean. 2 bedrooms located on the main level (1 new queen sized bed, and 2 new twin beds complete the other bedroom). 1 bedroom on the lower level with new king sized bed, and 2 new queen sized pull out couches in 2 roomy living areas. Updated kitchen appliances and two bathrooms on main level with 1 1/2 bathrooms on lower level. An acre of ocean front property with privacy to enjoy your vacation, House at Table Rock is the perfect place for summer, fall, and winter vacationers. brbrWe offer Weekly Rental and 3 to 4 night stays during certain times of the year, Please inquire accordingly.

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Bath

Sleeps

$626.75

/ Nightly

Private Vacation Home

Back yard paradise

Portland, Maine, United States

Wake up to the sounds of chickadees (Maine’s state bird), you sip your coffee in this furnished family home. With exceptional morning light, a 2 minute drive to the airport, and a 6 minute drive to Portland’s downtown, this is the perfect location for a weekend getaway. Enjoy the Portland trails which are close by. After a day of exploring Portland, enjoy the backyard paradise which includes: an in ground swimming pool, vegetable gardens, patio, grill and fire place. Enjoy your staybr

Bed

Bath

Sleeps

$645.24

/ Nightly

Private Vacation Home

The best place for the money!!!

Portland, Maine, United States

Heart of the West End, which is on the peninsula and part of the downtown. Quiet neighborhood, but nice bars and restaurant 1-2 blocks away. The night life is only 6-7 blocks. Great for entertaining with 2 off street parking spots & a large fenced in patio. Inside is all hardwood and tile, open concept with large kitchen, living room and dining room on the first floor. Upstairs is 3 bedrooms & a bathroom w/washer & dryer. Each room has a queen bed with one room being extra large (master)

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Bath

Sleeps

$552.7

/ Nightly

Private Vacation Home

Rare Single Family Home in Munjoy Hill Neighborhood

Portland, Maine, United States

This single family home in Portland's Munjoy Hill neighborhood offers 3 bedrooms, including 2 queen beds and 1 sofa bed, perfect for a serene getaway for a couple or small family. Enjoy all of the convenience of home during your stay, including a dog-fenced back yard. Very convenient location with several restaurants, coffee shops and bars close by. Go a little further (8 minutes walk) in one direction to explore the East End Promenade and Beach (swimmable!) or walk the other way to get to Old Port / downtown in the same amount of time. 30 day stay minimum, discounts available for 12+ months.

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Bath

Sleeps

$2135.59

/ Nightly

Private Vacation Home

Art Filled East End Home a short walk to waterfront, restaurants and shops

Portland, Maine, United States

Exquisitely decorated, art-filled home on Portland's highly sought after East End. Stunning water views from the master bedroom and roof deck. Walking distance to Portland's restaurants and shops. 3 bedrooms, 2 full bathrooms and a powder room. Wonderful kitchen with dining table that seats 8 comfortably. A few blocks to the beautiful Eastern Prom park and waterfront, and a short walk into the Old Port and all the

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Bath

Sleeps

$1264.4

/ Nightly

Private Vacation Home

Stylish & Spacious Townhouse w/Garden, Family-friendly, walk to downtown!

Portland, Maine, United States

Our light-filled three story home is perched on a lovely, quiet corner of the historic West End residential neighborhood and is walking distance to all of Portland's finest. One of the rare properties right in town with a spacious back deck for meals al fresco, and a backyard big enough for kids to enjoy, the house is very well-appointed and roomy, perfect for families or a few friends traveling together. Three bedrooms (king, queen + twin, twin) and master bath on the third floor, and one bedroom (queen) and full bath on the second floor. It's a great hub from which to explore both the vibrant city life nearby, as well as all the natural glories of Southern Maine. Whether you want to plunge into Portland's world class culinary scene, catch the current show at The Portland Museum of Art, attend the latest event at Space Gallery, take the ferry to Peaks Island, picnic at Kettle Cove, bird watch at the Audubon, or hit the outlets in Freeport and Kittery, you'll find our home a comfortable home base to return to. We are willing to reduce our rate for stays of a month or longer. Portland License # STHR-005034-2023

4

Bed

2

Bath

8

Sleeps

$285.22

/ Nightly

Private Vacation Home

Rare, Single-Family Home In Desirable Munjoy Hill Neighborhood Near To Ocean

Portland, Maine, United States

10 Emerson St. is a lovingly restored 1870 New Englander located in the heart of the Munjoy Hill neighborhood and just 2 short blocks from the Eastern Promenade and amazing views of Casco Bay's islands. Three of Portland’s top restaurants are just around the corner and Hilltop Coffee Shop, Rosemont's natural foods market, and St. Lawrence Performing Arts Center are only a block away. brbrThe house has been completely renovated inside and out over the last 10 years and contains designer furnishings. This is a two-story, airy and bright house with a completely renovated walk out lower level offering a third floor of living area. There are three full bathrooms, one on each floor (including the lower level). The master bedroom contains a queen size bed and a walk out to a private deck. The adjoining bathroom has a walk in shower. The second bedroom is furnished with a queen-size bed. Entering the first floor you will find a living room, dining room, kitchen, full bathroom (with claw foot tub) and mudroom. The living room contains a 42”flat-screen TV with Roku player and surround sound. Both the first and second floors have high ceilings and hardwood floors.brbrThe multi-functional, bright, walk-out lower level is uniquely designed by an architect and features a central family room complete with Queen sofabed (NOT NECESSARILY IDEAL SLEEPING FOR OLDER PEOPLE DUE TO BEING LOW TO THE GROUND), desk area, wood stove and a modern, in-home theater system based around a 100” projection screen. The third bathroom is located in the lower level and functions as a designer wet room. The lower level also contains a kitchenette and laundry facilities. The outside living space includes an intimate, lush, dining area and a well-landscaped, English, garden-style courtyard, including exterior lighting and a fountain.brbrThe property has high-speed internet, Roku players with access to TV, Netflix and Amazon services.

Bed

Bath

Sleeps

$501.07

/ Nightly

Private Vacation Home

Convenient Portland home 3 miles from Downtown

Portland, Maine, United States

A Great Escape awaits you at this gorgeous Portland gem! This perfect Maine get away sits in a quiet residential neighborhood, but is located just a few miles from the waterfront, downtown, the historic Old Port and many Maine coastal beaches. It is also just a short walking distance to one of Portland's great Italian restaurants and bars, and within a short drive from Dunkin Donuts, Starbucks, numerous fast food places and much more.brbrThis freshly renovated 3 bed 1.5 bath single family home (approx. 1600 sq. ft.) has everything you need. It is extremely clean, spacious and is conveniently located to everything you need. The entire house is yours and includes:brbr* Fully loaded kitchen with granite counters and tiled floors. It's like being at home.brbr* Oversized leather couch with multiple reclining seats and matching leather recliner. brbr* 60 tv in the living room with access to Netflix, Prime, Hulu, or your favorite APP (with guests log in). Cable is provided for free via Spectrum streaming.brbr* Brand new dining table that comfortably seats 8 along with board games, puzzles and cards.brbr* Master bedroom includes a Tempur-Pedic King bed that has head and feet adjustable components and a 55 smart tv. brbr* Second bedroom includes King size, memory foam bed with 43 smart tv.brbr* The third bedroom includes a Queen size memory foam bed and a Twin size memory bed, along with a 43 smart tv. brbr* Free wireless internet.brbr*A Pack and Play is available for guest use. brbr* This home provides remote controlled heat pumps for AC/heat to maximize the comfort of all guests. brbr* A washer/dryer set is available on the second floor near the bedrooms. brbr* There is a commercial elliptical for use in the basement for those who want some fitness on their Great Escape!brbr* DVD player and sitting space in the basement for kids to have fun.brbr*Generous backyard area for backyard games, a front porch, a small backyard deck, and a garage for two cars. There is also a driveway for extra parking that could fit up to an additional four cars. brbrYou cannot beat this home for your Great Escape to the Portland, Maine area!

3

Bed

1

Bath

7

Sleeps

$272.5

/ Nightly

Private Vacation Home

Winter rental - Bright and charming townhome atop Munjoy Hill. 11/1/25- 5/31/26

Portland, Maine, United States

This delightful two-story property offers two comfortable bedrooms with queen beds, a freshly updated bathroom with a bathtub, and all the essentials, including AC and heating. Just steps from the Eastern Prom and the water, and around the corner from cozy cafés and restaurants, it strikes the perfect balance between a peaceful retreat and vibrant city living—all within easy walking distance. Perfect cozy winter rental.brAvailable 11/1/25- 5/31/26

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Bath

Sleeps

$593.38

/ Nightly

Private Vacation Home

Evergreen cottage 5' from the water with private beach.

Portland, Maine, United States

The cottage is situated on a bluff 5' from the water at high tide. 270 degree ocean views. Listen to the waves and bell buoys as they put you to sleep at night. Simple Maine cottage charm interior on the first floor level includes a large screened in front porch, a good size living room/dining room area with a newer well equipped kitchen and an updated bathroom with shower. The second floor has 5 small bedrooms(watch your head!) and a very small half bath. The property has its own private beach area. Kayaks are available to use, please bring your own safety equipment. 2 car off street parking included. City of Portland License Number STHR-002599-2020.

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Bath

Sleeps

$1280.75

/ Nightly

Private Vacation Home

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Portland, Maine, United States

Welcome to your home away from home in Portland, Maine! This charming six-bedroom, three-bath Craftsman-style house offers a rare combination of character, comfort, and location. Whether you’re planning a family reunion, friends’ getaway, or group retreat, you’ll have plenty of space to relax and enjoy stunning views of Casco Bay and the Presumpscot River — all just minutes from the vibrant Old Port.brbrThis home is ideal for groups seeking space, comfort, and proximity to Portland’s best attractions — all with the charm of a historic Craftsman and the bonus of unforgettable views.brbrHighlights you’ll love:brbr* Breathtaking water views from multiple roomsbrbr* Private hot tub for year-round relaxationbrbr* Large back patio & screened porch with seating, fire pit, and grillbrbr* Two driveways + free street parking for 5–6 vehiclesbrbr* Walkable / short drive to restaurants, shops, and waterfront walking trailsbrbrSpacious & comfortable layout:brbr* 6 Bedrooms:brbr2 × Kingbrbr1 × Queenbrbr1 × Full + Twinbrbr1 × Fullbrbr1 × 2 Twinsbrbr* Extra sleeping: 1 Queen sleeper sofa, 1 Full sleeper sofabrbr* 3 Bathrooms – 1 per floorbrbr* Multiple living areas – two with TVs, one with a gas fireplacebrbrFully equipped kitchen & dining:brbrThe open-concept main floor features a cozy living room with a fireplace, a large dining table perfect for group meals, and a pass-through to the fully outfitted kitchen. You’ll find everything you need: coffee maker, blender, microwave, toaster, full cookware set, bakeware, dishes, glassware, and utensils.brbrExtras for your comfort:brbr* Laundry room with 2 washers & 2 dryersbrbr* Fresh linens, towels, robes and extra blankets/pillowsbrbr* High-speed Wi-Fi for work or streamingbrbr* Board games & books for cozy evenings inbrbrOutdoor Living:brbrGather around the fire pit on the furnished patio, or enjoy a game of corn hole or bocce in the large yard. After a day exploring Portland, soak in the hot tub under the stars.

Bed

Bath

Sleeps

$578.47

/ Nightly

Private Vacation Home

Historic Island Retreat on Great Diamond Island with resort like amenities!

Portland, Maine, United States

Stay in the original Surgeon’s Quarters on Great Diamond Island! This 2BR/2BA historic brick home blends charming details with modern updates. Enjoy wooded views from the screened porch and full access to Diamond Cove amenities: pool, fitness center, basketball court, bowling alley, private beaches, and more. Just a scenic ferry or water taxi ride from Downtown Portland—your perfect island escape awaits!brbrWelcome to 171 Diamond, a rare opportunity to stay in the original Surgeon’s Quarters at Fort McKinley on Great Diamond Island. This beautiful 2-bedroom, 2-bath freestanding brick home blends historic details with thoughtful modern upgrades—tin ceilings, original fireplace, a gas stove, custom window treatments, and hardwood floors.brbrEnjoy peace and privacy from your screened-in back porch with serene wooded views. You’ll also have access to a grill and picnic table perfect for BBQs. Inside, the home is fully furnished with tasteful decor and a fully equipped kitchen, making it perfect for a cozy week away or extended getaway.brbrFor helpful details about the house, getting to the island, and some of our favorite local recommendations, we’ve created a welcome guidebook for our guests. It includes information about the home, island amenities, things to do on Diamond Island, and great spots to explore in Portland during your stay. If you’d like to review it before booking, feel free to send me a message and I’d be happy to share the link with you!brbrAs a guest, you’ll have full access to all the Diamond Cove Homeowners Association amenities, including:brbrRA van service to and from house from Ferry/dockbrHeated outdoor pool (seasonal late May-late September) brFitness centerbrIndoor basketball courtbrTennis & Pickleball Courts brDuckpin Bowling Alley and Game Room brMultiple private beachesbrA playgroundbrOn-island restaurants - Diamonds Edge and Crown Jewel (seasonal)brbrJust 2 miles from Portland in Casco Bay, a scenic ferry ride transports you to a peaceful, car-free island with rich history, coastal charm, and natural beauty. Whether you're collecting shells at the beach, relaxing poolside, or exploring island trails, 171 Diamond offers the perfect island escape!brbrGetting to Diamond Island: Diamond Island is accessible by boat only. Guests can arrive via Casco Bay Lines ferry service from Portland or by private water taxi, such as Fogg’s Water Taxi. Travel times and schedules vary by season.brbrPlease message the host before your arrival for additional details on transportation options, scheduling, and recommendations. We’re happy to help coordinate and answer any questions to make your arrival as smooth as possible.brbrBedrooms/Bathrooms: Bedroom 1 features a queen bed and a private en-suite bathroom with a walk-in shower. Bedroom 2 includes 1 full sized bed and 1 twin bed. A second full bathroom with a tub is located in the upstairs hallway. All bedrooms and bathrooms are located on the 2nd floor. Portland Short Term Rental License: STHR-007450-2025

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