Vacation Home Rentals By Owner In Portland, ME

Welcome to Urban Ease, your elevated Portland stay-where modern finishes, spacious interiors, and thoughtful amenities create the perfect balance of comfort and convenience. Nestled in a quiet neighborhood, this apartment offers a peaceful retreat while keeping you just minutes from Portland’s vibrant arts, dining, and waterfront scenes. Ideal for families, business travelers and groups looking for a stay.brbr 5 min-Back Cove Trailbr 8 min-Old Port br10 min-Museum of Artbr10 min-Victoria MansionbrbrLicense Number: STHR-003971-2022brbr→ Sleeps 8 | 3 Bedrooms | Queen Bedsbr→ Queen Air Mattress for additional guestsbr→ Sofa bedbr→ 2.5 Bathroomsbr→ Fully equipped chef-style kitchenbr→ Dining area + bar seatingbr→ Dedicated workspacebr→ Smart TV, books & board gamesbr→ High-speed Wi-Fibr→ In-unit washer & dryerbr→ Pack ’n Play for familiesbr→ Free on-site parking + free street parking nearbybrbr☆☆ BEDROOMS ☆☆brbrOur bedrooms are tranquil retreats designed for deep relaxation. Each room is a customized sanctuary featuring premium high-thread-count linens and individual split-system climate control for personalized comfort. The decor is thoughtfully curated, ranging from serene nautical blue accents to sophisticated wood finishes and mid-century modern furniture, creating a high-end boutique atmosphere.brbrBeyond the beds, you will find stylish and practical details throughout the sleeping quarters. Every room includes functional touches like arched gold-framed mirrors, designer rugs, and ample storage in spacious dressers. With ambient bedside lighting and cozy accent chairs, these rooms offer the perfect space to unwind after a day of exploring.brbrFor additional sleeping flexibility, the home also includes an air mattress available for guests when needed.brbr☆☆ BATHROOMS ☆☆brbrThe property features two modern, light-filled bathrooms designed for comfort and convenience. The first offers a spa-like experience with a large glass-enclosed shower featuring elegant mosaic tiling, a spacious marble vanity, and an integrated LED mirror. brbrThe second bathroom is equally functional, providing a clean, minimalist design with a full bathtub, glass sliding doors, and charming floral accents. Both spaces are equipped with large windows for natural light and premium finishes to ensure a refreshing stay.brbrbr☆☆ KITCHEN & LIVING AREA ☆☆brbrThe home features two fully equipped kitchens and expansive social areas that are naturally bathed in sunshine. Each kitchen is designed with a modern aesthetic, boasting sleek charcoal cabinetry, high-end stainless steel appliances, and large islands that double as breakfast bars. These bright, open spaces flow seamlessly into the dual living rooms, where elegant coffered ceilings and plush sectional seating. One comfortable sofa bed for additional sleeping space are highlighted by the abundant natural light and direct access to a private balcony, extending the living space outdoors and creating an airy, inviting atmosphere.brbrThe property offers two distinct dining areas perfectly suited for hosting large groups. The main dining space features a grand wooden table that comfortably seats eight, set under a sophisticated ceiling design that creates a formal yet inviting atmosphere for shared meals. A second, more casual dining area provides additional flexibility, ensuring there is plenty of room for everyone to gather, eat, and socialize without ever feeling crowded.brbr☆☆ LOCATION ☆☆brbrStay close to Portland’s best attractions while enjoying a quiet residential setting.br - Arts District (10 min) – Museums, galleries, cafés, and creative energy.br - State Theatre (10 min) – A historic venue hosting live performances and concerts.br - Old Port & Eastern Promenade (10 min) – Waterfront views, cobblestone streets, shops, and restaurants.br - Payson Park (8 min) – Expansive green space with recreation areas and trails.br - Fort Allen Park (12 min) – Scenic views of Casco Bay and historic landmarks.brbr☆☆ COMFORT & CONVENIENCE ☆☆brbr✔ High-speed Wi-Fibr ✔ Smart TVbr ✔ Books & board gamesbr ✔ Hair dryer, fresh linens, and towels providedbr ✔ Coffee makers (Keurig + drip)br ✔ In-unit washer & dryerbr ✔ Pack ’n Play for familiesbrbrGuests have full private access to the home, including all three bedrooms, two full bathrooms, the spacious living area, fully equipped kitchen, dining space, and dedicated workspace. Enjoy the convenience of in-unit laundry, Smart TV, high-speed Wi-Fi, and mini-split heating and air conditioning in every room. A high chair is also available for families.brbrFree on-site parking is available for one vehicle, with additional free street parking nearby. Entry is easy and secure via smart lock, and exterior security cameras provide added peace of mind. The home’s central location offers quick access to Portland’s restaurants, waterfront, arts scene, parks, and local attractions.brbrBy booking, you accept responsibility for any damage or extra cleaning they may be required during the stay.brbrSchena Group Properties, LLC, guests are automatically protected by the Waivo® damage protection program. The program offers the industry’s broadest protection. It’s damage protection done right.

Urban Ease/By Downtown/Parking

Portland, Maine, United States

Bed

Bath

Sleeps

$524.29

A beautiful, elegant, and relaxing property on an island with all that Maine living should be, and only a 15 minute Fogg taxi ride from Portland. Explore the beaches, forts, and batteries. Decompress, write, paint, compose! I find I think more clearly, creativity is enhanced, and general perspective is expanded. .4 miles from Diamond Cove ferry dock, and .6 from Great Diamond dock. License # STHR-007680-2026brbrComfortably sleeps 6. brGolf cart includedbrmultiple beachesbrTennis and pickle ball courts out backbrPool (summer)brFull fitness centerbrIndoor basketballbr2 island bikes for adults or bigger kidsbrPicnic table and charcoal grillebrAll the kitchen essentials (a dishwasher and lobster pot)brGuitarbrLinens and towelsbrLL Bean ComfortersbrDaily Grocery Delivery

Cozy townhouse minutes from downtown Portland on a car free island

Portland, Maine, United States

3

Bed

1

Bath

6

Sleeps

$752.1

Welcome to your dream retreat on Diamond Cove, a captivating island oasis just a short ferry ride from Portland, Maine. Sitting proudly on the former parade grounds, our spacious vacation rental promises a perfect blend of modern comfort and timeless recreation, making it an ideal escape for families and friends.brbrThis three-bedroom, two-and-a-half-bathroom gem spans over 2,600 square feet, ensuring ample space for relaxation and enjoyment. Inside you are greeted by an inviting atmosphere, tasteful furnishings, coastal-inspired decor, and an abundance of natural light filtering through large windows.brbrThe heart of the home lies in its open concept living area with a well-equipped kitchen seamlessly transitioning into a comfortable living space. Gather around the fireplace for cozy evenings or step out onto one of three porches to savor the island air. An expansive stairwell leads to three private bedrooms, each thoughtfully designed to offer a peaceful retreat after a day of island adventures. Indulge in worry-free relaxation at our vacation rental, equipped with everything your little ones will need, including a crib, high chair, and sippy cups, ensuring a family getaway filled with joy and ease.brbrOutside you will discover a world of community amenities right at your fingertips. Take a dip in the pool, challenge friends to a game of basketball or tennis on the courts, or try your hand at pickleball. The nostalgic arcade, complete with duck pin bowling and billiards, provides entertainment for all ages. A fully equipped gym and yoga room are also available.brbrWhip up a feast in the well-stocked kitchen or explore the island’s trio of restaurants including the popular Crown Jewel and the classic Diamond's Edge. With five beaches, picnic areas, and recreation spaces, Diamond Cove ensures there's always something to do. brbrFor the history enthusiast, Diamond Cove provides an opportunity to explore the trails leading to the historic sites of Fort McKinley. Immerse yourself in the rich heritage of the island as you wander through the well-preserved remnants of this military installation. Or dive deeper with a guided tour through the Fort McKinley Museum. brbrBeyond the island's charms, a 30-minute ferry ride transports you to the vibrant Old Port in Portland. Explore the historic streets, indulge in local cuisine, and soak in the rich culture of this coastal city before returning by ferry to the tranquility of Diamond Cove.brbrWhether you're seeking an active getaway or a serene escape, this vacation rental on Diamond Cove offers something for everyone. Create core memories in a welcoming home surrounded by the beauty of Maine's coastline, where adventure and relaxation seamlessly coexist. Your island retreat awaits, promising an unforgettable experience on the Casco Bay.brbrFeatures of the home:br- Primary suite - king bed and attached full bathbr- Bedroom two - queen bed and cribbr- Bedroom three - two twin bedsbr- Hall bathroom - full bathbr- First floor - powder roombr- Fully equipped kitchenbr- Three large porchesbr- Two smart TVsbr- Gamesbr- Washer and dryerbr- WiFi br- Air Conditioning (mini-split on first floor)brbr brCommunity Amenities:br- Community pool br- Five beachesbr- Picnic areasbr- Hiking trailsbr- Playgroundbr- Arcadebr- Duckpin bowling alleybr- Basketball courts (indoor and outdoor)br- Tennis courtbr- Pickleball court (indoor and outdoor)br- Yoga studiobr- Fully equipped gymbr- Restaurants (summer season only)br Crown Jewelbr Diamond’s Edgebr The Lobby Bar & Cafe (Inn at Diamond Cove)br- Island storesbr The Market at Diamond’s (small store with necessities, penny candy, and drinks)br Crown Jewel General Store (breakfast sandwiches, coffee, ice cream, and wine)br brPlease note:brDiamond Cove is an island community; personal cars are not allowed, and a ferry is required to access the island. You will be assisted with getting your luggage and provisions to our home. To make your planning easier, a full list of stores that deliver to the island will be provided. All provisions must be brought onto the island when you arrive or by delivery. brbrbrPolicies:brNo smokingbrNo pets allowedbrNo events, parties, or large gatheringsbrYou must be 25 years old or older to bookbrMust follow community quiet hoursbrMax overnight occupancy of 6

Coastal Island Retreat in Diamond Cove, Casco Bay

Portland, Maine, United States

Bed

Bath

Sleeps

$443.99

7 minutes from downtown Old Port, accommodating 4 guests in comfort with 2 bedrooms, a/c, wifi, full bath, half bath, kitchen, living room, dining areas, office, gas grill, outdoor patio seating and more, this private single family home offers ~1,300 sq ft in a quiet neighborhood of Portland, Maine.

Quiet Family Vacation Home in Portland, Maine 7 minutes to the Old Port

Portland, Maine, United States

Bed

1

Bath

6

Sleeps

$377.52

Coveside Island Retreat | 2BR Duplex with Sauna & Pool AccessbrbrUnplug and unwind at this cozy two-bedroom, one-and-a-half-bath apartment on beautiful Great Diamond Island — part of a peaceful duplex just steps from the water. Ideal for families or small groups, this island getaway offers a perfect mix of comfort, charm, and exclusive resort-style amenities.brInside, you’ll find a queen bed in the primary bedroom and two twin beds in the second, with an additional full bed and TV in the finished basement—perfect for extra guests or movie nights. You’ll also enjoy a private sauna, a washer and dryer, and a fully equipped kitchen that opens to a bright living area.brOut back, relax on the fenced-in deck with a BBQ grill and take in the quiet surroundings or head to the open-air front deck with rocking chairs and a wraparound lawn — a perfect spot for morning coffee or sunset drinks.brbrA short walk brings you to the Crown Jewel Restaurant and the island general store, while your stay includes access to exclusive Coveside amenities:br- Heated swimming pool (with pool bar access)br- Six private beachesbr- Tennis & pickleball courtsbr- Duckpin bowling alley & indoor basketball courtsbr- Fitness center & yoga studiobr- Waterfront dining at Diamond's Edge Restaurant & MarinabrbrWhether you're swimming, strolling, playing, or just relaxing in the sauna, this is the island escape you've been dreaming of.brbrCome get away. Your island retreat awaits.

Cozy Coveside Island Retreat

Portland, Maine, United States

Bed

Bath

Sleeps

$686.03

Wonderful cottage style home with spectacular views and direct access to your own waterfront. Perfect for kayaking, SUP, fishing or enjoying the abundant birdlife. 3 minutes to downtown Portland's Old Port, restaurants, galleries, museums, micro brews. Walking distance to Mackworth Island State Park, rocky beaches, neighborhood restaurants and groceries. Relax on the deck with friends for breakfast, cocktails or dinner. Enjoy coffee from second floor deck off master bedroom. Nicely landscaped, always a cool breeze with off street parking. Built in 1915, the home has new on demand hot water system, lighting and original artwork throughout.brRecent renovations include hardwood kitchen flooring and new master bath. While new to VRBO, I have rented my home in the past and all of the guests loved their stay. Slate Pool Table, stereo, HD TV, WIFI included. Simply furnished, with two bedrooms, p living room, billiard room and two full baths. Nicely equipped kitchen with DW, microwave, coffee maker, toaster and new stainless refrigerator. Water views abound including Portland Headlight. brThere are less than 25 homes in the city of Portland with waterfront property. This is one of them.brBTW, Coffee and chilled bottle of Prosecco await new guests!

Wonderful Portland Waterfront Home

Portland, Maine, United States

Bed

Bath

4

Sleeps

$677.44

Welcome to Harmony House- your Portland retreat-where comfort, convenience, and city charm come together. This thoughtfully designed home offers an inviting living space just minutes from Portland’s vibrant waterfront, arts scene, and dining hotspots. Whether you're visiting with family, working remotely, or exploring Maine’s coastal beauty, this home is the perfect place to recharge after a day of adventure.brbr 5 min-Back Cove Trailbr 8 min-Old Port br10 min-Museum of Artbr10 min-Victoria MansionbrbrLicense Number: STHR-003971-2022brbr→ Sleeps 8 | 3 Bedrooms | Queen Bedsbr→ 2 Full Bathrooms with shower/tub combosbr→ Fully equipped kitchen with full-size appliancesbr→ Dining table seating 8br→ Dedicated workspace for remote workbr→ Smart TV + High-speed Wi-Fibr→ Washer & dryer in unitbr→ Mini-split heating & AC in every roombr→ High chair for familiesbr→ Free on-site parking + free street parking nearbybr→ Private balcony off the main living areabrbr☆☆ BEDROOMS ☆☆brbrOur three bedrooms are designed as serene retreats, blending coastal-inspired decor with modern comfort. Each room features premium bedding and thoughtful lighting, ranging from the nautical charm of the first room with its blue accents and individual climate control, to the sophisticated warmth of the second bedroom, which offers ample storage and a stylish workspace vibe.brbrWith queen-sized setups, the rooms provide flexible sleeping arrangements for all guests. You will find elegant touches throughout, such as full-length mirrors, designer rugs, and curated artwork, ensuring a restful and high-end experience that makes you feel right at home.brbr☆☆ BATHROOMS ☆☆brbrEach bathroom offering a unique aesthetic that ranges from contemporary chic to classic elegance. Guests can choose between refreshing glass-enclosed walk-in showers featuring custom mosaic tiling or unwind in full bathtubs equipped with sliding glass doors. Premium finishes are evident throughout, including marble countertops, sleek pedestal sinks, and high-end fixtures in varied finishes like matte black, polished chrome, and vintage brass.brbrDesigned for both comfort and style, these spaces are bright and airy, with windows that invite natural light to bounce off the crisp white subway tiles and intricate floor patterns. Thoughtful touches such as large mirrors, curated artwork—ranging from floral prints to coastal landscapes—and ample storage space ensure a boutique hotel experience. A convenient half-bath with a modern vanity rounds out the facilities, ensuring plenty of space for everyone to get ready with ease.brbr☆☆ KITCHEN & LIVING AREA ☆☆brbrNaturally bathed in sunshine, the social heart of this property features an expansive open-concept layout that seamlessly connects the fully equipped kitchen with the main living areas. Each kitchen is designed with a modern, high-end aesthetic, showcasing sleek charcoal or white cabinetry paired with premium stainless steel appliances and spacious islands that double as breakfast bars. These bright culinary hubs flow effortlessly into the dining spaces, where a grand wooden table for eight serves as a central point for shared meals and gatherings under elegant coffered ceilings.brbrThe living areas are similarly flooded with natural light, highlighting the plush sectional seating and sophisticated décor. With dual lounge spaces available, the home offers flexibility for large groups to either congregate together or find a quiet corner to relax. Every detail, from the ambient integrated lighting to the large windows and direct access to the private balcony, is designed to create a warm, inviting, and airy atmosphere throughout the day.brbr☆☆ LOCATION ☆☆brbrStay close to everything while enjoying the comfort of a residential neighborhood.brbrArts District (10 min) – Explore museums, galleries, local cafés, and creative energy along Congress Street.brbrState Theatre (10 min) – A historic venue hosting concerts and live performances.brbrOld Port & Eastern Promenade (10 min) – Cobblestone streets, waterfront views, boutiques, and top restaurants.brbrPayson Park (8 min) – A large green space with sports fields, walking areas, and outdoor recreation.brbrFort Allen Park (12 min) – Scenic coastal views over Casco Bay and historic landmarks.brbrGuests have full private access to the home, including all three bedrooms, two full bathrooms, the spacious living area, fully equipped kitchen, dining space, and dedicated workspace. Enjoy the convenience of in-unit laundry, Smart TV, high-speed Wi-Fi, and mini-split heating and air conditioning in every room. A high chair is also available for families.brbrFree on-site parking is available for one vehicle, with additional free street parking nearby. Entry is easy and secure via smart lock, and exterior security cameras provide added peace of mind. The home’s central location offers quick access to Portland’s restaurants, waterfront, arts scene, parks, and local attractions.brbrBy booking, you accept responsibility for any damage or extra cleaning they may be required during the stay.brbrSchena Group Properties, LLC, guests are automatically protected by the Waivo® damage protection program. The program offers the industry’s broadest protection. It’s damage protection done right.

Harmony House/Walk to Downtown/Parking/Balcony

Portland, Maine, United States

Bed

Bath

Sleeps

$1458.42

Brand New Listing! Experience the best of Portland, Maine in this stunning, newly built home just steps from the working waterfront, world-class restaurants, boutique shops, and everything that makes Portland one of New England's most beloved destinations.brbrThoughtfully designed for groups up to 11, this spacious home offers an effortless blend of comfort, style, and function across three floors. The heart of the home is a chef's dream kitchen featuring a six-burner Wolf range, two dishwashers, and generous counter space — perfect for everything from a leisurely breakfast to an elaborate dinner party. This house is equipped with an elevator. The open-concept first floor flows seamlessly from kitchen to dining to living, creating an inviting space for gathering. Step outside to a deck with a gas grill that leads to a covered porch — ideal for morning coffee or evening cocktails in any weather.brbrFour bedrooms | 4.5 baths Two en-suite bedrooms offer private retreats, with an additional full bath serving the remaining bedrooms on the second floor. The open floor plan finished third floor provides flexible bonus space with its own full bath.brbrArriving by car No problem. The street level garage accommodates 3–4 vehicles — a rare luxury in Portland.brbrWhether you're planning a romantic escape, a family reunion, a friends' getaway, or a working retreat with colleagues, this home delivers an experience that's hard to match.

Steps from Old Port. New, Beautifully Appointed Home. Sleeps up to 11.

Portland, Maine, United States

Bed

Bath

Sleeps

$267.05

This Portland house boasts 1 inviting bedroom with 1 king bed on the second floor. A sleeping loft with 1 queen bed with no door to access the bedroom you walk through the loft area. While there is laundry available access to the basement is a very steep set of stairs with a vey low ceiling. The 1st floor bath comes equipped with a hair dryer for your convenience. Step inside this adorable retreat and feel right at home. Relax in the cozy living space or whip up a delicious meal in the fully equipped kitchen. Book now and enjoy everything this house has to offer.

Cozy, Quiet and Convenient

Portland, Maine, United States

Bed

Bath

Sleeps

$2563.32

Summary:brEnjoy the flexibility of 3 condos in this 1849 mansion that can accommodate up to 18 guests. Off street parking for 6 cars, private patio and 10 minute walk to Old Port.brbrLicense# STHR-004723-2022 & STHR-005205-2023brbrThe Space:brEnter through the historic front entry of the 1849 Cpt. Ingraham into the foyer. To the left, is unit one which features 2 bedrooms and 1.5 bathrooms and can accommodate 6 guests. At the top of the stairs, you will find two units that together provide 3.5 bathrooms, 4 bedrooms each with a queen bed and two sofa beds with additional sleeping for 4 guests. brbrbrUNIT ONE: Two Queen bedrooms w/queen sofa bed. (6 guests)brbrThe unit is uniquely divided between the first floor and lower level. Up the side stairs, you will enter through a private entrance.br brYou will enter into the kitchen area, which features a full kitchen stocked with everything you would need to prepare a meal in house. A full bathroom with in unit washer/dryer is off of the kitchen. Around the corner you will find a large office for working from home as well as a queen pull out sofa. On the right side of the entry, is a spacious living room with a fireplace (non-working). brbrOn request, the living room in this unit can be set up for dining with banquet tables and seats 12.brbrDown a set of stairs from the kitchen are the bedrooms. Each bedroom has a queen bed with premium mattresses and bedding. There is plenty of hanging storage and space to relax. One bedroom features a half bath. There is also a walk out door to the parking area for easy access to bring in luggage. br brbrUNIT TWO: One Queen Bedroom w/ full couch bed (4 guests)brbrThe second unit is on the second floor and to the right of the home. It features black and white accents and newly remodeled space. Step into a living room and well equipped kitchen space with high end appliances. The bathroom features a classic black and white mosaic floor and subway tile with duel rainfall and adjustable shower heads. It also features a grohe smart control. A stacked LG ThinQ washer/dryer finishes the space. brbrUNIT THREE: 3 Queen Bedrooms w/ 2 Queen sofa beds (10 guests)brbrThe third unit, features navy blue accents, skylights, historic brick walls, and wood beamed bedrooms. It encompasses the left side of the second floor and the entire third floor. The unit features a large living room with sectional. A bar table has seating for 8 and flows into a kitchen space with high end appliances and a half bath. Off of the kitchen is a private office space with a door that offers a queen pull out sofa and desk. brbrUp a second set of stairs, you will find 3 bedrooms and two full baths. The primary bedroom has a queen pull out sofa with en suite full bath. The other two bedrooms share a hallway full bath with a dual vanity, shower and washer/dryer.

Historic 1849 Sea Cpt. Mansion; Weddings, Groups

Portland, Maine, United States

Bed

Bath

Sleeps

$647.46

Step into a piece of Portland history in this beautifully restored 3BR/2BA home, built in 1874 and updated with care over 20 years by its owner. With room for 12 guests, a fully stocked kitchen, private backyard with patio, fast Wi-Fi, and off-street parking, you’ll have the comforts of home right in the heart of Portland’s best dining, nightlife, and coastal charm.brbrBright Queen SuitebrThe Queen Suite is a peaceful retreat bathed in soft natural light, with a plush queen bed, classic hardwood floors, and rich custom millwork that echoes the 1874 origins of the home. Thoughtfully appointed with blackout curtains and ample storage, it's perfect for watching the city wake up or winding down after a day exploring Portland.brbrKing RetreatbrRelax in the spacious King Retreat featuring a luxurious king size bed, high ceilings above, and elegant wood detailing throughout. Ideal for couples or guests seeking extra comfort, it includes generous closet space and a serene atmosphere for restorative rest.brbrDouble Bed Guest RoombrDesigned for families or small groups, this guest room offers two full-size beds nestled among the home's original hardwood floors and custom wood trim. It's warm, inviting, and flexible for your group’s needs; whether it’s kids, friends, or extra guests sharing a cozy space.brbrLofty Double NookbrUpstairs in the loft you’ll find a charming nook with a double bed, tucked beneath a vaulted ceiling. This elevated space captures the home's history, perfectly balancing privacy and character for guests who enjoy a touch of whimsy and morning light.brbrBathrooms:brbrClassic Bath with TubbrDiscover a stately full bathroom complete with a vintage style tub, full-size shower, and a pedestal sink inviting you to unwind after a day out on the coast. Period-inspired fixtures complement the historic ambiance, updated for modern comfort.brbrContemporary Powder RoombrThe sleek second bathroom offers a walk-in shower, elegant fixtures, and thoughtful light. Ideal for quick refreshes or supporting a larger group with efficiency and style.brbrLiving & Dining Areas:brbrSunlit Living RoombrGather in the light filled living area, where high ceilings, original woodwork, and comfortable seating await. Board games, books, and streaming-ready entertainment create a communal haven for nights in or quiet mornings with coffee.brbrKitchen and DiningbrThe fully stocked gourmet kitchen features modern appliances including a recently upgraded oven and plenty of counter space. A large communal table encourages group meals and conversation, perfect for cooking with family or friends.brbrOutdoor & ParkingbrbrPrivate Backyard OasisbrStep outside to your own private backyard oasis, outfitted with outdoor furniture, dining space, and a grill. Whether you're enjoying a morning cup of coffee in the sunshine or hosting a twilight barbecue, it’s the ideal private escape in the heart of the city.brbrRare Off Street ParkingbrEnjoy the rare convenience of private tandem parking right on site an invaluable perk in downtown Portland. No stressing over street permits; just park and go!brbrYou will have a custom code matching the last four digits of the phone number on filebrbrI am available anytime for anything you may need during your stay! No interaction is required but I am always happy to answer any questions or provide local recommendations.brbrWhile the top two floors are exclusive to the unit, there are two single occupancy studio apartments on the first floor with separate entrances.brAdditionally the stairs to the loft bedroom are quite steep so they may not be suitable for everyone.

Spacious Portland Home + Parking

Portland, Maine, United States

Bed

Bath

Sleeps

$983.0

Summary:brbrBrand-new luxury coastal home minutes from Portland’s Old Port. Relax in the 8-person hot tub, gather around the fire pit, and enjoy a beautifully appointed chef’s kitchen designed for memorable group getaways. A private deck overlooks the garden with a play area, play kitchen, crib, pak n play and fire pit, while a covered gazebo shelters the year-round spa. Perfect for families, friends, or remote work, with easy access to beaches, Portland’s dining scene, and waterfront attractions.brbrbrbrThe Space:brbrClick the ❤️ icon to save our property to your wishlist! ❤️brbrbrbr Escape to Portland’s Seaside Getaway – A Brand-New Award Winning Design Custom Built Luxury Coastal Retreat brbrbrbrBrand-new luxury coastal home just minutes from Portland’s Old Port.brbrRelax in the 8-person hot tub, gather around the fire pit, and enjoy a chef’s kitchen designed for unforgettable group getaways.brbrbrbrModern Elegance | Spacious King & Queen Suites | 8-Person Hot Tub | Heart of Portland Near Old PortbrbrbrbrWelcome to Seaside Getaway, your exclusive escape in the heart of Coastal Maine. Located in Portland’s desirable North Deering neighborhood—just minutes from vibrant Falmouth, the beaches, and downtown Old Port—this award-winning, custom-built 2024 retreat blends timeless coastal charm with sophisticated, high-end design. Whether you're here to unwind, explore, or both, Seaside Sanctuary delivers the perfect balance of relaxation, luxury, and adventure.brbrbrbr❤️ Highlights of Key Amenities ❤️brbrbrbr• 8-person hot tub under covered gazebobrbr• Outdoor fire pit & private garden deckbrbr• Gourmet chef’s kitchenbrbr• Sleeps 10 comfortablybrbr• Outdoor dining & BBQ grillbrbr• Fast WiFi for remote workbrbr• Luxury coastal brand new custom built Award Winning design throughoutbrbr• Karaoke Machine with two mics ready for the entertainers in the family!!! brbrbrbr❤️ Mom’s love our life size fully stocked toy play kitchen and other toys to keep the kiddos happy and occupied!! ❤️brbrbrbr ❤️ So Mom, Dad and the Kids can relax and enjoy the day and night away on vacation!! ❤️brbrbrbrFor Mom & Baby — Crib + Pack ’n Play Ready ❤️brbrbrbr ️ Luxury AccommodationsbrbrSleeps up to 10 guests comfortably across 4 elegant suites (1 King Master Suite with insuite Full Bathroom and 3 Queen Suites). Three bathrooms in total. brbrbrbr❤️ One Queen Suite is located on first floor for older family member that would prefer no steps ❤️brbrbrbrPlush luxury premium traditional mattresses beds, premium linens, soft-touch bedding, pillows, and designer furnishings.brbrbrbrIn addition to the premium mattress and high quality bedding, we also offer one Queen Sealy air mattress to ensure everyone has a comfortable place to sleep.brbrbrbrFamily-friendly: Includes Baby Crib, Pak’N’PLAY, high chair, play toy kitchen setup, toys, games and kid-friendly open concept layout.brbrbrbr ️ Gourmet Kitchen and Large Open Concept Living SpacesbrbrOpen-concept floor plan with soaring 10' ceilings and sun-filled interiors floor to ceiling windows to enjoy memorable visits with your family and friends!brbrbrbrChef’s kitchen fully outfitted with premium appliances, ideal for home-cooked meals or private chef servicesbrbrbrbrElegant décor, custom lighting, and tasteful coastal accents throughoutbrbrbrbr Outdoor OasisbrbrPrivate garden deck with views of a peaceful creek and lush landscaping with a fire pit for the fireside chats with family and friends!brbrbrbrRelax year-round in your covered 8-person hot tub under the stars with gazebo roof—the perfect spot for stargazing or enjoying a glass of winebrbrbrbrOutdoor dining area, BBQ grill and firepit for evening gatheringsbrbrbrbr Unbeatable LocationbrbrJust minutes from Old Port’s historic waterfront, ocean beaches, lakes, shopping, mini-golf, PGA golf course, water parks, and outstanding diningbrbrbrbrEasy access to Ocean beaches, Casco Bay beaches, Mackworth Island, trails, Casino, top-rated golf courses, you name it and we have it in Coastal Maine.brbrbrbrWithin a short drive of resorts, casinos, and scenic drives to the Mountains and Lakes Regionbrbrbrbr Easy Travel & ConnectivitybrbrClose to Portland Jetport, Amtrak, Concord Coach, and METRO Bus LinesbrbrbrbrUltra-fast 2 GIG fiber optic WiFi – perfect for remote work or streamingbrbrbrbrPlenty of parking on-site and EV-friendly areabrbrbrbr Smart Amenities & Concierge-Level HostingbrbrbrbrSmart lock key padbrbrbrbrSmart home features throughout: thermostats, TVs, Sonos speakersbrbrbrbrResponsive hosts available throughout your stay for personalized supportbrbrbrbrStreaming-ready with Apple TV, YouTube TV, Netflix, and more (subject to guest logins)brbrbrbr Why Stay at Seaside Sanctuary brbrBrand-new 2024 award-winning designbrbrbrbrThe best of Portland and Coastal Maine within easy reachbrbrbrbrA private, peaceful setting with resort-level luxurybrbrbrbrThere is a separate unit with tenants on the adjacent unit located on property, with its own private entrance separate and distinct.brbrbrbr Book your stay today and discover the magic of Maine’s coast—where timeless New England beauty meets refined modern comfort. Whether you're planning a romantic escape, a family gathering, or a friends' retreat, Seaside Sanctuary offers the perfect setting to relax, explore, and create unforgettable memories.brbrbrbrGuest Access:brbr❤️ Experience ultimate relaxation in our luxury retreat featuring a King Master Suite and three Queen Suites, a gourmet custom kitchen, and an open-concept living/dining area. Step outside to a cozy deck and private backyard, complete with a high-end 8-person luxurious spa hot tub overlooking a serene creek and tranquil gardens. Wake up to birdsong and enjoy a peaceful space for reading, meditation, and wellness—a perfect escape where luxury meets nature. Make this is your family and friends memorable moments in Maine! brbrbrbrWe can wait for you to experience our brand new home!!brbrbrbrThe Neighborhood:brbrLovely North Deering Area is a lovely neighborhood of Portland. Mature walkable neighborhood with mature trees, landscape, bike/running path and many other outdoor activities. Shopping and Restaurants nearby.brbrbrbrGetting Around:brbrOur property is conveniently located close to Portland and Coastal Maine. There are many restaurants, coffee shops, and recreational facilities within walking distance. You can also easily access Maine's ocean beaches, Lake Sebago, beaches and boat ramps by car. The property is located close to many popular destinations within a 1.5-2-hour drive to Acadia, Bar Harbor, and 10-15 min ride to great beaches such as Cape Elizabeth, Old Orchard Beach, Kennebunkport, Brunswick, LL Bean & Outlets in Freeport. Short ride to Sunday River, Mt Washington, New Hampshire, Boston and many surrounding attractions, We are less than 2.5 from the Old Port and all popular Portland Old Port, Water Front attractions, restaurants, museum, and shoppingin a short 5-10 mins away. Bar Harbor, Acadia, Cadillac Mountain, Moosehead, Mt. Washington, and many others attractions are a reasonable drive away! Come see and enjoy the adventure of Maine's Vacation Land. You will love it!!!!brbrbrbrThe Greater Portland METRO Stop is only a 2-3 minute walk from the property, and there is regular Concord Bus Service to Boston Logan Airport, Downtown Boston and beyond. The AMTRAK station is just a short ride away (2.7 miles). The Portland Jetport (PWM) is only 4 miles away.brbrbrbrInteraction with Guests:brbrWe’re here to make your stay exceptional! If you need anything at all, simply reach out via text to your dedicated HOST, and we’ll promptly assist with any request or recommendation to enhance your experience. Our goal is to ensure every moment of your time here is seamless, enjoyable, and truly memorable. Relax and feel at home—we’re just a message away to make sure your stay is absolutely perfect!brbrbrbrClick the ❤️ icon to save our property to your wishlist! ❤️

Luxe Coastal Retreat with Hot Tub & Fire Pit

Portland, Maine, United States

4

Bed

3

Bath

10

Sleeps

$1297.45

West End Chic is a Bright, Spacious Home with Unique Touches & Family-Friendly Fun! brbr***Please Read Full Property Description Before Booking!***brbrWest End Chic is an large, old home built in 1867. While much of the first floor has been beautifully updated with modern finishes, the second and third floor maintain their period charm and character. brbrAIR CONDITIONING:brThis home does not have central air. br- Air conditioning (window units) is only available on the 2nd and 3rd floor of the house. Every room on those floors has A/C. br- The first floor does not have A/C, but there are fans available. This part of the house is very well shaded and does not typically require air conditioning. brbrFIRST FLOOR: brThe first floor is a wonderful place to gather with friends and family! br- Modern Chefs Kitchenbr- Kitchenettebr- Laundry Roombr- Dining Roombr- Two Sitting Rooms (White and Orange)br- Half BathroombrbrSECOND FLOOR:brTravel up the grand spiral staircase to the second floor, or go up the back steps located in the kitchen (these ones are steep!). br- Sitting/TV Room (The red one)br- Master Bedroom (KING) with Ensuitebr- Kids bedrooms (TWIN) shared Jack and Jill Bathroombr- Kids bedroom (FULL) shared Jack and Jill BathroombrbrTHIRD FLOOR: brSteps to the third floor are steep and narrow. Please plan accordingly.br- Pool Table Room w/ kitchenettebr- Full Bathroombr- Bedroom (FULL and TWIN)br- Master Bedroom (QUEEN) with EnsuitebrbrSPACIOUS LIVING AREASbr- Enjoy the light-filled interior with eclectic art and one-of-a-kind furnishingsbr- Cozy up by the fireplace with a good bookbr- Formal dining table for family meals & great conversationsbr- Living area ideal for socializing and relaxingbrbrFUN & GAMESbr- Pool table for a friendly competitionbr- Large TV for movie nightsbr- Piano and toys to keep little ones entertainedbrbrOUTDOOR MEMORIESbr- Patio furniture and grill for enjoying the peaceful evenings. brbrOTHER THINGS TO NOTE:br- Free parking for two vehicles, with a Level 2 EV chargerbrbrbrLICENSE # STHR-006332-2024

West End Chic - Chef's Kitchen, Pool Table, W/D

Portland, Maine, United States

Bed

Bath

Sleeps

$408.75

Charming, Secluded, Island Getaway for family and friends!brbrThis Down-front getaway has all the advantages to make your vacation the most relaxing it can be. Anyone looking for a peaceful and quiet retreat while still wanting access to urban amenities will love this place. This home is appealing during Maine’s lovely and relaxing carefree days of summer on an Island.brThe house is only a block away from the crashing surf and the ocean breezes tickling your nostrils. The house is a five minute walk from the Casco Bay Ferry, Peaks Island Post Office, the Island’s general store and of course fabulous restaurants on and off the Island in Old PortbrThe Be Chill Cottage is only a block from the crashing surf. It offers leisurley strolls by the seashore, the salt air and sea roses. This lovely house has a master bedroom with a queen-size bed, a second bedroom with a double-bed and a fold out couch in the main living area. The kitchen has granite counter tops, new appliances and is updated with all the essential kitchen equipment for that perfect meal. Best of all it has the essential lobster pot! The living area is quite spacious and open throughout. It offers internet and cable TV. The front deck perfect to sit out and watch the sunsets. The back deck walks out into the grassy yard that has a gas barbecue, picnic table and Adirondack chairs for those unforgettable evenings on Peaks Island.brThere is a warning however! We visited the Island and fell in love with it and the Portland area in general. We ended up moving to Peaks Island. Maybe this will happen to you!

Charming, Secluded, Island Getaway!

Portland, Maine, United States

Bed

Bath

Sleeps

$348.8

Adorable almost new Peaks Island cottage. Three bedrooms, openbrkitchen, living area with awesome, comfortable window seat. Sunnybrdeck. Peeks at the water through the trees. Quiet street, one minutebrwalk from back shore ocean, ten minute walk to ferry. (The ferry runsbrevery hour and is a 15 minute ride into the Old Port section of Portland, ME) Cottagebrhas sleeping room for six: master bedroom--one queen bed,brsecond bedroom--one full bed, upstairs loft--one twin bed, one set of twin bunks, one queen bed. W/D, dishwasher, wifi throughout, DVD/TV, gas grill. Pets OK with extra charge. New, sunny, outdoor enclosed shower with hot water added summer of 2022.

Peaks Cottage: Modern amenities, island charm, steps to shore

Portland, Maine, United States

Bed

Bath

Sleeps

$801.54

Stay in historic elegance at 87 Pine Street, a charming landmark home in Portland’s sought-after West End. Enjoy spacious rooms, original architectural details, and modern comforts. Perfectly located, it’s a short walk to the Old Port, renowned restaurants, breweries, and the scenic Western Promenade. Ideal for families, couples, or groups.brbr Please note that this property is townhouse in the West End and has multiple (3) flights of stairs within the unit. brbrSPACE: This lovingly preserved historic home offers 3 bedrooms with 4 comfortable beds, ideal for families or groups. Relax in cozy living areas, enjoy natural light through large windows, and prepare meals in the fully stocked chef’s kitchen. Historic details blend beautifully with modern amenities, including high ceilings, tasteful furnishings, and ample space to unwind after exploring Portland.brbrACCESS: Guests have private access to the entire unit, including all bedrooms, living spaces, kitchen, and bathrooms. Feel completely at home throughout your stay.brbrINTERACTION: Professionally managed by Everrow Property. Guests have private access to the entire unit, including all bedrooms, living spaces, kitchen, and bathrooms. Feel completely at home throughout your stay.brbrNEIGHBORHOOD: Located in the West End, one of Portland’s most historic and walkable neighborhoods. Enjoy leafy streets, charming architecture, and a tranquil atmosphere. Walk just 10 minutes to the Old Port, Arts District, award-winning restaurants, breweries, and boutiques, or explore the Western Promenade for beautiful views of the Fore River.brbrTRANSIT: The neighborhood is highly walkable, with downtown Portland and key attractions just minutes away on foot. Public transportation, bike shares, and rideshare services are conveniently available, making exploring Portland easy and enjoyable.brbrNOTES: License Number: STHR-006709-2025brPlease no pets on the furniture. Do not leave any perishables out at the end of your stay. No smoking on the property. Please observe quiet hours from 10pm until 7am.brbrGuests with Children: While children are welcome in our home, please note that the property has not been childproofed. It may not be suitable for very young children or those requiring a child-safe environment. We ask parents to supervise their children closely and accept responsibility for their safety and wellbeing during their stay.brbrLate check out is not offered at this listing. Early check in is possible based on our reservation calendar and if we have guests leaving that morning. brbrThank you!

The 87th Townhome - Local Landmark

Portland, Maine, United States

Bed

Bath

Sleeps

$3051.67

Stay in one of Portland’s most sought-after neighborhoods—the historic West End—where tree-lined streets, classic architecture, and a refined residential feel meet unbeatable walkability to everything the city has to offer.brThis beautifully preserved historic building has been thoughtfully updated and offers a rare opportunity for larger groups: a few units combined into one expansive stay featuring 5 bedrooms and 3 bathrooms. Ideal for wedding groups, family reunions, birthday celebrations, and multi-generational travel, the layout provides the perfect balance of gathering together while still enjoying private space. While the home is made up of individual units, it flows easily for groups, allowing everyone to stay connected without feeling crowded.brSpanning the second and third floors, the home includes multiple living areas, kitchens, and sleeping spaces, making it easy to spread out while still enjoying time together.brEnjoy two private outdoor decks, perfect for morning coffee, relaxing afternoons, or unwinding in the evening after a day exploring Portland.brThe location is exceptional—and incredibly walkable. Step outside and you’re immediately surrounded by neighborhood favorites, including restaurants, cafés, bakeries, and local shops—giving you that true Portland experience right at your doorstep but in a quieter city neighborhood.brbrOld Port restaurants, shops, and cafes are just a short walk awaybrPortland’s waterfront is also easily accessible on foot, offering working wharves, scenic views, and boat activitybrMuseums, galleries, and live music venues are all nearbybrPark your car and explore Portland entirely on foot.brDespite its central location, the West End remains quiet and residential—offering a more elevated and peaceful experience than staying directly in the busy downtown core.brbrParking is easy and flexible:brFree on-street parking is available. Just a few doors down, there is also a convenient metered lot (approximately $20/day), which is free overnight and includes electric vehicle charging stations. An additional paid parking lot is located within a short 2-minute walk for added convenience.brPlease note: This home is located in an upscale residential neighborhood and is best suited for respectful guests. It is ideal for gatherings, but not parties or events.brWhether you're in town for a wedding, reunion, or group getaway, this property offers a rare combination of space, historic charm, and walkable access to Portland’s best attractions.

Spacious West End Retreat, Walk Everywhere, Prime Portland Location

Portland, Maine, United States

Bed

Bath

Sleeps

$256.21

East End AnnexbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWithin easy walking distance of bakeries and restaurants, this comfortable abode boasts a superb location, quality furnishings, and an inviting interior. Stroll approximately a half mile to the Eastern Promenade and take in views of the bay and islands. Here you can rent kayaks and explore the open waters, relax on the beach, and enjoy the Portland food trucks. Catch the Casco Bay Ferry that takes you to the local islands and walk around historic Old Port.brbrAfter a fun day exploring the town or taking in the surrounding natural beauty, guests will love returning to this home to relax on the sofa while a favorite movie plays, make use of the well-equipped kitchen, and spend quality time together on the deck. brbrTHINGS TO KNOWbrGuests must use their own accounts to access streaming platforms.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 3.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Munjoy Hill hideaway with AC - walk to dining & Eastern Promenade

Portland, Maine, United States

Bed

Bath

Sleeps

$639.2

Pearl of PortlandbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis downtown Portland property hosts two separate, fully equipped living spaces that are perfect for a family or group of friends in need of space and privacy. (Please note that the two individual portions of the home have separate entrances and are not connected.) Two contemporary kitchens and living rooms, cable TV and Netflix streaming, and a cozy gas fireplace all create a homey environment for you to return to after your Portland adventures. brbrWhat's nearby:brLocated just half a mile north of Portland's Old Port, this property places you within easy walking distance of several local eateries and charming shops. Casco Bay Lines ferry is close by, offering scenic rides out on the Atlantic Ocean. Also nearby are the Merrill Auditorium for fascinating performances and the educational Portland Observatory. Best of all, East End Beach is only a mile from your front door, offering the perfect place for you to soak up some vitamin D on the sand and swim in the ocean waves.brbrThings to know:br*The two individual portions of the home have separate entrances and are not connected. They can also be booked separately for smaller parties. See Cumberland Charm and A Foodie's Delight for further details.brFree WiFibrTwo full kitchensbrTwo sofabeds includedbrPlease note that there is a tenant living full-time in the upstairs homebrbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Portland, Maine, United States

Bed