Home Vacation Rentals By Owner In South Portland, ME

Showing 20 Of 39 Vacation Rentals
Slider Thumb
Exceptional(22)

$462

/ Nightly
Private Vacation Home

OCEAN VIEWS, Rooftop Deck, HOT TUB, new back deck! 3-min walk to Willard Beach

South Portland, Maine, United States

BRAND NEW VACATION HOME. 150 yards to Willard Beach, 8 mins to downtown Portland, Walk to fantastic restaurants/food shops. Portland was named by Thrilist as The #1 City in the country to spend the weekend, The most underrated food city in the US and The Best Drinking City:, It was also rated by Bon Appetit as the US's 2018 Restaurant City of the Year which also ranked Portland years ago as The Foodiest Small City in the Country. Willard Beach was rented the 2nd prettiest beach in Maine in 2018.brbrThis stunningly beautiful, fully-renovated beach house is the quintessential Maine Beach house. Painstakingly renovated by a regionally-famous designer for over 12 months, the brand new home is now available as a vacation rental for the first time ever. The designer's work on this home has received national attention and the home is featured on the popular Cottage Living, House of Turquoise and Hooked on Houses websites and in the April 2018 issue of The Old House Journal magazine. brbrThis beautiful 2125 sq. ft. 4 bedroom, 2.5 bath home features a huge and fabulous rooftop deck with expansive ocean views and luxury appointments throughout. 2 KING beds, 3 QUEEN beds, 1 DOUBLE, one extra regular TWIN bed (upon request). brbrPlease see my other listings if your dates are reserved:** brbrDowntown condo with 3 Bedrooms and 2.5 BathsbrVRBO #903832 with 4-5 Bedrooms and 2 Baths brVRBO #1660664 with 4-5 Bedrooms and 3.5 BathsbrVRBO #4019326 with 3 Bedrooms and 1.5++ Baths (sleeps up to 8)brVRBO #1885186 with 7 Bedrooms and 4.5 Baths (sleeps up to 27)brbr**And for warm weather getaways, please see our homes in Scottsdale, ArizonabrVRBO #1958654, #2926813 and another stunning and very large/luxurious coming soon home in norther Scottsdale, Arizona**brbrThis gorgeous beach house offers a very private Master Bedroom suite with full bathroom and marble double sink vanity, double tiled shower. KING bed with luxurious Beauty Rest Black mattress, absolutely gorgeous new Pottery Barn bedding and luxurious 100% Egyptian Cotton Percale sheets. Extra twin bed in frame with new high-quality mattress and new pack 'n play are both available upon request. Window A/C.brbrSecond Bedroom: DOUBLE bed in fun nautical theme with RH bedding ensemble and luxurious 100% Egyptian Cotton Percale sheets. Blackout shades and window A/C. Bedroom not shown in photos.brbrThird Bedroom: Very sunny back bedroom with QUEEN bed with Pottery Barn linen nailhead headboard, gorgeous Serena and Lilly Bedding, fantastic mattresses and luxurious 100% Egyptian Cotton Percale Sheets. Blackout shades, window A/C.brbrFourth Bedroom: Sunny front bedroom with beautiful verdi gris iron QUEEN bed. 100% Egyptian Cotton Percale Sheets and gorgeous bedding from Anthropologie. Window A/C.brbrHuge Ocean View Deck: plenty of lounge seating with 2 coffee tables and a bran new therapeutic massage hot tub with ocean views. brbrPlease let us know if you would like to bring pets with you, as they are considered on a case by case basis and must be approved prior to arrival. Please do not leave pets unattended in the house with the windows open (noise from barking dogs inside houses in this area can be heard by many neighbors).brbrFREE WIFI.
Bed 4

Bed

Bath 3

Bath

Sleep 12

Sleeps

Slider Thumb
Exceptional(3)

$879

/ Nightly
Private Vacation Home

WALK TO BEACH! 3 bedroom beautiful home in walking distance to Willard beach!

South Portland, Maine, United States

Just a few blocks from Willard Beach this 3 bedroom Colonial is perfect for 2 couples or a family with children. A rare find with its 9-foot ceilings, hardwood floors, tons of natural light. Enjoy a large open floor plan on the main level. Fully stocked kitchen with stainless steel appliances and gas stove for a great cooking experience. Granite counter top bar to enjoy a cocktail while talking to the chef. Large dining table that can comfortably seat up to 8 people. Large spacious living room leading to sunny 3 season sunroom. Half bath on main level. Three large bedrooms on second floor two with a comfortable queen size bed and one with a twin bed and/or crib if needed. The master has a beautiful deck attached overlooking the backyard and occasional peek of the ocean. The master has a full bath attached with walk in tiled shower and the other two bedrooms share a full bath with his/her sinks. brbrSmall backyard recently updated with patio and firepit! Large gas grill outside for you to use. Full access to 4 beach chairs and an umbrella. The front porch is a great place to relax and enjoy a warm summer day while sitting in the rocking chairs or in the swing.brbrEasy 3 minute walk to get a famous bagel from Scratch Bakery and Willard scoops for delicious homemade ice cream. Davids and Elsmere BBQ restaurant are only a short walk away. Or head down to Willard Beach with your kayak and enjoy easy beach living. 7 minutes to Portland's Old Port. Bring your road bikes for some of the most scenic bike rides in the state.brbrThinking of throwing a house party This is NOT the house for it. Please do not inquire. Out of consideration for our neighbors and our family who regularly enjoy our home, we only seek mature, responsible renters who will leave our home in the same excellent condition in which they found it at check-in.brbrNon-refundable, pay upfront discount rate option is available. Inquire if interested.brbrAll payments are non-refundable, so trip cancellation insurance is always encouraged!
Bed 3

Bed

Bath 3

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(61)

$224

/ Nightly
Private Vacation Home

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

South Portland, Maine, United States

South Portland CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis new 1BR South Portland cottage is perfect for a couple but offers plenty of space for entertaining. You’re just 10 minutes from all of the historical buildings and restaurants of downtown Portland. Take a boat cruise or stroll through town. Sleeps 2.brbrABOUT THE COTTAGEbrbrEnter this brand-new, yet quaint cottage through white barn doors. The open-concept floor plan welcomes you with red, heated concrete floors, natural light, and designer décor.brbrIn the spacious living room, you’ll find a sofa, love seat, and a red leather chair. Invite your friends over for an evening of games and sampling of local craft brews. Or make hot cocoa and snuggle up with your mate in front of the 64” flat-screen TV for a movie marathon.brbrThe kitchen features granite counters, stainless appliances, and a 5-burner gas range. (There’s also a grill, stored out front—perfect for a seafood supper.) Grab a seat at the bar (4 stools) and sip a glass of wine while someone else does the cooking.brbrFollow the hardwood steps up to find a full bath with white tiled flooring and a tub/shower combo. The large vanity offers plenty of space to spread out.brbrJust beyond, the master features a king bed with white linens. Stay up to catch the late show on the 48” flat-screen TV.brbrYou can pack light for this trip because a stacked washer and dryer are tucked in a closet in the bedroom.brbrOn rainy days and cold nights you can stay occupied with the books, board games, Play Station, and complimentary WiFi.brbrThis South Portland cottage combines comfort with charm and is the perfect spot for a romantic getaway.brbrPlease note that all leases require a minimum 31-night term.brbrTHE LOCATIONbrbrThis brand-new cottage is located just 10 minutes from downtown Portland. History lovers won’t want to miss the Old Port, Portland Observatory, and Wadsworth Longfellow House. Stroll along the Eastern Promenade and gaze out at the bay.brbrWhen you’ve worked up an appetite, there are plenty of options for every palate. For an authentic waterfront experience, check out Andy’s Old Port Pub. If you’re in the mood for international cuisine, try Asmara, featuring the flavors of Eritrea. And for a sweet treat, Beal’s Ice Cream is always a hit.brbrFor an over-water adventure, take a ferry or cruise to see the Casco Bay Islands. If you’re an aficionado of craft brew, Maine Beer Tours has you covered. And animal lovers will appreciate the Odyssey Whale Watch.brbrWhen you need to pick up groceries, there are several farmers’ markets that run from April to November. Deering Oaks Park (Saturdays) and Monument Square (Wednesdays) are 2 of the best.brbrOr stay closer to the cottage and visit the Ocean House Market, a local favorite, less than a half mile away. They offer fresh seafood as well as prepared meals and sandwiches.brbrThree miles from the home, you’ll find a private parcel of land with beach access—a great spot to catch some rays in the summer or to stroll year-round.brbrParking notes: There is free parking available for 1 vehicle.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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(7)

$399

/ Nightly
Private Vacation Home

Willard Square Family Home

South Portland, Maine, United States

Charming colonial nestled in the bustling heart of the neighborhood! A quick stroll takes you to Scratch Bakery & Willard Scoops, perfect for treating the entire family's taste buds. Start your day with a leisurely walk to Willard Beach, where you can catch the joyful sight of pups frolicking in the waves. And yes, furry friends are invited too! Explore a vibrant array of attractions just blocks away, including upscale dining, cozy eateries, and eclectic boutiques & antique stores.brYour hostsare only 5 minutes away should you need anything. We are so fortunate to be a part of such a wonderful community.brbrWelcome to Willard Square!brWillard Beach was formerly called Gurry Cove in the 1870’s and the beach was lined with small fishing shanties. The beach is now named for the Willard family who settled the cove and became successful fishermen. In the late 1800’s and early 1900’s the fishing shanties were slowly replaced by summer cottages.brbrWe have beach chairs, beach towels, a beach table, umbrella, coolers, and a wagon to cart all your stuff down to the beach in! brbrRest assured, high-touch surfaces are cleaned and disinfected for your arrival.Sheets and towels are washed at 60°C/140°F or hotter.We follow regional cleaning and disinfection practices of COVID-19 Health & Safety Standards and industry cleaning and disinfection practices of COVID-19 Guidelines (CDC).
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

Select Dates for Price
Private Vacation Home

Comfortable, family-friendly home just steps from Willard Beach!

South Portland, Maine, United States

Welcome to our charming vacation home, located just steps away from the picturesque Willard Beach in South Portland. This sought-after destination provides the perfect getaway to explore everything this area has to offer. Enjoy the beauty of the local beach and its breathtaking sunsets. Take a leisurely stroll along the enchanting beachside path to the Spring Point Lighthouse. For your daily dose of coffee and baked goods, Scratch Bakery is just a short walk away, and an evening walk to the local ice cream shop is always a delightful treat.brbrOur home itself is a rare gem, offering a high standard of quality for your South Portland vacation. It has undergone a recent addition, blending spaciousness, brightness, and modern comforts with a warm and inviting atmosphere. Spread across two floors, the home boasts a stairwell, bathroom, and primary bedroom that all offer ocean views. The property provides tandem parking for three vehicles, a fenced yard, a spacious, open-concept first floor, back deck and patio with abundant seating and a back yard with chairs, a fire pit, hammock, a trampoline and other toys for the kids, And of course, you'll be just steps away from the amazing Willard Beach! Grab one of our stand-up paddle boards and explore Casco Bay.brbrOur house is air-conditioned so you can cool off on those hot summer days. Stay connected with complimentary wireless internet access throughout the property, and enjoy the entertainment provided by the smart television in the living room. Our home is conveniently located just an 8-minute drive from downtown Portland, allowing you to easily explore the fantastic restaurants and food shops in the area. brCome and experience the charm and convenience of our vacation home, where the beach is just steps away and endless adventures await in beautiful South Portland.
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(1)

$144

/ Nightly
Apartment

Stunning South Portland Apartment w/Pool

South Portland, Maine, United States

Beautiful renovated South Portland 1 bed, 1 bath apartment in the Meeting House Hill neighborhood. This unit has incredible original stained glass windows in both the living room and kitchen. The fully stocked kitchen and dining area open to the living room, allowing for a convenient flow between the spaces. There's plenty of space for a work from home setup. The queen bedroom is upstairs, along with the full bathroom and laundry. Outside, you can enjoy the shared patio, yard and in-ground pool.brbrWelcome to your home away from home in South Portland! Experience the charm and history of this former convent building, with the original high ceilings and stained glass windows. This spacious 1 bedroom, 1 bathroom apartment has an open concept living area that is perfect for relaxing or a work from home setup. The kitchen is fully stocked for cooking and has stainless steel appliances and granite countertops. The queen bedroom upstairs is stylishly decorated and has plenty of storage space with a dresser and closet. Down the hall, the bathroom has a walk-in shower and tub, as well as a stacked washer/dryer.brbrCentrally located, the apartment is in a quiet neighborhood close to shops, restaurants, museums, breweries and state parks. There is a shared courtyard with outdoor seating and an in-ground pool for your enjoyment, as well. brbrIt's the perfect spot for couples, solo adventurers or business travelers looking for an extended stay.brbrOnly twenty minutes from Portland international Jetport and the Amtrak station. A quick 5-10 minute drive gets you to the iconic Spring Point Ledge Lighthouse (built in 1875), Fort Williams Park Greenbelt Walkway trail, Maine Mall and multiple beaches, including Willard Beach (1 mile), Kettle Cove and Ferry Beach.brbrThis is one apartment in a multi unit building. The unit has one parking spot and has a private entrance.brbrAlways available for questions, but never overbearing.brbrWe have installed exterior only security cameras for the safety of both guest and property. These cameras are actively recording both audio and video on all exterior entrances and side doors. Any tampering with cameras, including, but not limited to covering and otherwise disabling of these cameras are grounds for early termination of reservation with no refunds whatsoever.brbrAbsolutely no smoking inside or near open exterior doors - there is a $250 fee if this is violated.brbrPlease note that is not a pet friendly unit.brbrPlease note that any refunds made in accordance with our cancellation policy will be less any credit card fees.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Home Most popular vacation rentals in South Portland