Home Vacation Rentals By Owner In South Portland, ME

Showing 20 Of 36 Vacation Rentals
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Exceptional(26)

$285.58

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Apartment

Sunny Spot with Private Parking.

South Portland, Maine, United States

This cozy, 1 bedroom apartment is located in the peaceful neighborhood of Knightville.brThe Portland Peninsula, which includes the historic Old Port and the downtown arts district, is less than a 10-minute drive across the bridge.brbrThe perfect spot for a couple or a fun friend getaway!brbrSeveral excellent dining spots, coffee shops, and markets are all within walking distance from the house.brBike rentals are 2 blocks away!brbr*Willard Beach is a 5-minute drive from the house. (10-minute bike ride)br*Portland Head Light & Fort Williams Park are a 16-minute bike ride from the house. (A 9 minute drive)br*Beautiful Crescent Beach is a 14-minute drive from the house.brbrThis apartment has 10-foot high vaulted ceilings with skylights throughout that fill the place with afternoon sun. brThe living room area features an open floor plan which includes a full kitchen, living room, and dining nook. (See photos for more details of the layout.)brThe spacious bedroom has a queen-sized bed, a full-sized dresser, and a desk and chair for working remotely.brIn the living room area, the loveseat sofa folds out flat to a small single bed. There is a memory foam mattress topper available to go on top for added comfort.br(If you would like to use the single sofa bed just let us know in advance, and we will leave out linens etc. for you.)brbr*Please note. This apartment is on the second floor of the building brOnce inside, there is an additional flight of steps that leads up to the kitchen area.br**The last 11 steps leading up to the apartment are steep.brbr
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Bath 1

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Sleep 2

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$531.88

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Hotel

2 Modern Rooms for Family Getaway Next to Airport – With Free Breakfast

South Portland, Maine, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 12:00AM and 12:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. 2 pets max, dog/cat only, 75lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
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Bath 2

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Sleep 8

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Exceptional(9)

$687.33

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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).
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Bath 2

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Sleep 6

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$265.92

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2 QUEEN BEDS. HDTV 2 QUEEN BEDS. HDTV

South Portland, Maine, United States

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 12:00AM and 12:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $75 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. 2 pets max, dog/cat only, 75lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
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Sleep 4

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$673.62

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Condo

Arlie`s Digs! - One Block To Willard Beach!

South Portland, Maine, United States

Ground-floor, updated, 2-bdr condo in an historic 150-yr-old bldg. in the heart of Willard Square- steps from Portland `s friendliest beach and famous Scratch Bakery. Ideal for couples and families (including the pup). Here, you are just minutes from the Portland Headlight / Ft. Williams Park, the bustling Old Port and Portland’s world-famous restaurant scene. Enjoy the outdoors Hiking, skiing, snowshoeing and snowmobiling are a short drive away. Yes, Portland and Willard Square have it all!brbrNamed for one of our pups, Arlie`s Digs is a two-bedroom one bathroom condo unit on the ground floor of a three-story 150-year-old house that was converted to condos a few years ago. Original pine floors throughout. The bedrooms - one King and one Queen - have new mattresses, ceiling fans, closets, storage, lamps, and charging stations. The Living Room has seating for six+ with a 55-inch Samsung `smart` TV. The sofa is comfortable but is not a `sleeper` sofa. Also, separate desk and chair in LR with dedicated electrical outlet. The bathroom has a large shower and a full-sized front-loading washer and dryer. The kitchen has a gas range, a moveable mini-island with butcher block top, bar seating for 2, microwave, coffee maker, toaster, pots and pans (incl lobster pot), cups, glasses, dishes, etc. The separate dining room has a round dining table and a bar with glasses appropriate for your favorite drinks. A/C is provided by window units. Off the kitchen is a nice deck with a table and chairs w/ an umbrella, and a large grassy back yard which is not fenced, but is removed from the street.brbrOur guests have access to all of Unit 1. The driveway in front of the building (off Preble St) is reserved for Unit 1. The driveway accommodates two cars one parked behind the other (tandem). The driveway on the back of the building off Day Street is for Units 2 & 3. The yard is shared with Units 2 & 3. The Weber gas grill is just off the deck outside our kitchen door and is shared with the other units. The deck itself is technically shared by all three Units, but since Units 2 & 3 have decks on the other side of the building, there is usually no overlap.brbrWelcome to Arlie’s Digs at Willard Beach. We are beyond excited to have you as our guest! This neighborhood is very special to us. We moved to Maine just a few years ago, and walked our dogs Arlie, Foster and Atticus every day to dog-friendly Willard Beach and throughout the charming and very walkable surrounding neighborhood. They couldn`t get enough of Willard Beach during the early morning and early evening off-leash hours. brbrSouth Portland is a perfect location from which to explore the beautiful Maine coast, the City of Portland and The Old Port, Cape Elizabeth, Knightville/South Portland and, really, all of Southern Maine. Your accommodations are just steps from the famous Scratch Bakery and also Willard Scoops (ice cream shop); and a three-minute walk to Willard Beach. A 10-minute walk brings you to wonderful dining at David`s 388, tasty BBQ at Elsmere BBQ, DiPietro`s Market, Rosemont Market, donuts and sweets at the Cookie Jar, Omi`s Coffee Shop, Terra Cotta Pasta Company, and Thai Taste.brbrArlie’s Digs has dedicated two-car tandem parking right by the front door. Additionally, street parking is available on Preble Street. Note that street parking is restricted in the winter months for snow removal equipment. Please be mindful of the dates in effect. brbrIt is a ten-minute drive to Portland`s Old Port and Ft. Williams Park (Portland Headlight). Don`t feel like driving Uber and Lyft are available and South Portland does have city bus service - the schedule can be found at the city`s website.brbrJust off the entry hall is a door to the basement. The door is not locked, but there is nothing in the basement that a guest could use or would need. The stairs to the basement are steep and narrow and need to be avoided. Please stay out of the basement. Thanks!brPlease 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!
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Sleep 5

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$265.92

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Hotel

Cozy Room Next to the Airport w/ 2 Beds - Free Hot Breakfast & Shuttle

South Portland, Maine, United States

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 12:00AM and 12:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $75 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. 2 pets max, dog/cat only, 75lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
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Sleep 4

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$260.52

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Hotel

Comfortable Room Near Airport & Shops – Free Shuttle, Breakfast & Parking

South Portland, Maine, United States

This listing is for a room within a hotel.brbr✦ Your room is 231 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center is available, available in the property.brbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 12:00AM and 12:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $75 per night refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. 2 pets max, dog/cat only, 75lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
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Sleep 2

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Exceptional(22)

$1438.88

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Private Vacation Home

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

South Portland, Maine, United States

WILLARD BEACH 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 Foodiest Small City in the US and also the US's 2018 Restaurant City of the Year. Willard Beach was rented the 2nd prettiest beach in all of Maine in 2019.brbrThis stunningly beautiful, fully-renovated beach house is the quintessential Maine Beach house. Painstakingly renovated by a regionally-famous designer for over 12 months, this home is now available as a vacation rental. 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. brbrPLEASE NOTE: We have made recent (winter, 2025) improvements to the home as follows: brbr1. Newly installed tall privacy fence now surrounds the entire back yard and side yards with charming picket-style fronts and gates (on both sides of the front of the house). brbr2. Beautiful decorating changes to the Primary suite, including all new Serena and Lily bedding with stunning coordinating Serena and Lily wallpaper and new lighting. All windows have shades and blackout curtains have been added to the 2 largest windows.brbr3. ALL-NEW KING guest room. All new furniture, rug, artwork, mirrors, decorative items and new blackout curtains.brbr3. New decorative changes, rug, artwork in the second Queen Guest room.brbr4. Beautiful new decorative lighting and artwork have been added to the main level of the home, not all of which is shown in the photos.brbr5. All new dinnerware, service for 12, from the Crate and Barrel Marin line with every piece offered and all coordinating serving pieces.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, 2 QUEEN beds, and we can add one TWIN bed to one of the queen guest rooms (upon request). brbrThis gorgeous beach house offers a very private Primary Bedroom suite with full bathroom and marble double sink vanity, double tiled shower. All furniture is from RH. California KING bed with luxurious mattress, absolutely gorgeous new bedding with matching wallpaper from Serena and Lily and gorgeous new lighting, all recently added. All windows have window shades and the 2 largest windows also have blackout curtains. Window A/C.brbrSecond Bedroom: All new KING bedroom with everything new. All new furniture, bedding, artwork, mirrors and new blackout curtains. Room a/c.brbrThird Bedroom: Very sunny QUEEN bed with Pottery Barn linen nailhead headboard, gorgeous Serena and Lilly Bedding, fantastic mattresses and luxurious 100% Egyptian Cotton Percale Sheets. Brand new Serena and Lily rug, new mirrors, new artwork, new decorative items. 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. New rug, new vintage dresser and new artwork. Wide-slat blinds and Window A/C.brbrHuge Ocean View Deck: plenty of beautiful and plush lounge seating, all from Serena and Lily. 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).brbrbrbrbrbrFREE WIFI
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Bath 2

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Sleep 12

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Exceptional(2)

$416.34

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Apartment

The Coastal Connection

South Portland, Maine, United States

Welcome to The Coastal Connection, a bright and comfortable two-bedroom apartment in the heart of South Portland. This upstairs unit offers plenty of natural light, classic hardwood floors, and all the essentials for a relaxed Maine stay.brbrThe space is fully furnished with a newly stocked kitchen, so you can settle in and feel at home whether you’re here for a few nights or a longer visit. There are two cozy bedrooms, one bathroom, and an inviting living area perfect for unwinding after a day exploring the coast.brbrGuests enjoy free on-site parking and a location that couldn’t be more convenient—just minutes from I-295 and 10 minutes to Portland’s Commercial Street with its waterfront restaurants, shops, and breweries. You’re also 15 minutes from Higgins Beach and about 20 minutes from Old Orchard Beach, making it easy to experience the best of southern Maine’s coastline.brbrWhile this is an older building, its natural light and simple charm make it a pleasant and practical home base for exploring Portland, the beaches, and beyond. Whether you’re here for work, adventure, or a quiet getaway, The Coastal Connection is your easy link to it all.brPlease 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!
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Sleep 5

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$830.32

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Private Vacation Home

Steps to the Sand, Modern Home on Willard Beach, Fenced in Yard, Deck & Grill

South Portland, Maine, United States

Wake up to the sound of waves, enjoy coffee with ocean views, and step out onto the soft sands of Willard Beach—just a 30-second stroll from your front door. Whether you're here to unwind with your family, work remotely, or savor seaside sunsets with friends, this home has everything you need for an unforgettable summer getaway.brbr10 Minutes to Downtown Portlandbr8 Minutes to Portland Head Lightbr30 Second Walk to The Beach!brbrKEY FEATURES:brbr☀ Comfortably Sleeps 8 Guests: Spread out across 4 thoughtfully arranged bedrooms.br☀ Two Spacious Decks – Soak up ocean views from either of the brand new Trex decks, one with outdoor dining furniture for 8 and one with lounging furniture.br☀ Direct Beach Access – Walk out your front door onto Willard beach in about 30 secondsbr☀ Beach essentials provided: towels, a few beach chairs, beach umbrellabr☀ Fully fenced in back yardbr☀ WFH Ready – 350MB high-speed satellite WiFi br☀ Family & Dog-Friendly – Includes Pack 'n Play, high chair, and kid-friendly amenitiesbrbrbr☆☆ BEDROOMS ☆☆brbrEach bedroom is thoughtfully designed with comfort and style in mind, ensuring a peaceful and restful stay.brbrBedroom 1 (Main Level) – A cozy private sanctuary featuring a queen-size bed, a dresser for storage and convenient access to a private full bathroom—perfect for added comfort and privacy.brbrBedroom 2 (Smallest Room) – Perfect for kids or extra guests, this room includes a twin bunk bed and a spacious closet.brbrBedroom 3 – A queen-size retreat with a dresser and a closet for extra storage.brbrMaster Bedroom – A spacious and serene suite with a king-size bed, ensuite bathroom, dresser for storage, as well as a large walk-in closet for additional convenience. Enjoy ocean views right from the bed in this beautiful master suite.brbrbr☆☆ BATHROOMS ☆☆brbrThis home features 3.5 stylish bathrooms, thoughtfully placed for both convenience and comfort.brbrMaster Ensuite – A full private bath located within the master bedroom.brbrFirst-Floor Full Bathroom – Located within Bedroom 1 for added privacy and accessibility. Enjoy a brand new beautiful walk-in tile shower and glass doors.brbrGuest Full Bathroom – Centrally located near the remaining guest bedrooms. This bathroom has a shower/tub combo and was just renovated with a beautiful tile shower.brbrThird-Floor Powder Room – Conveniently placed near the kitchen and main living areas for easy guest access.brbrbr☆☆ KITCHEN, DINING, AND LIVING ROOMS ☆☆brbrLiving room – Spanning across the open-concept third floor, the living area is designed for both relaxation and connection. Large windows fill the space with natural light and offer water views from every angle. Whether you're curling up for a movie night with the Smart TV or gathering with friends after a beach day, this central space is warm, welcoming, and thoughtfully styled.brbrGourmet Kitchen – The gourmet kitchen is a chef’s dream—fully equipped with high-end appliances, ample counter space, and a walk-in pantry for easy organization. Whether you're preparing a casual breakfast or a full holiday feast, this space has everything you need to cook in style. brbrDining Area – Tucked into a cozy dining alcove on the third floor, the dining area comfortably seats up to 8 guests. Surrounded by windows and natural light, it’s an inviting space for everything from family dinners to game nights.brbrbr☆☆ OUTSIDE SPACE ☆☆brbrbrThe outside space of the home features a fully fenced in yard perfect for the dogs, two large decks with stunning ocean views and a gas grill for family barbecues, and of course the Maine ocean just steps away.brbrbr☆☆ ADDITIONAL GUEST EXPERIENCES ☆☆brbrLooking to make your stay extra special We partner with local businesses to help take your trip to the next level. We’re happy to help coordinate the following services:brbr☀ Kayak & SUP Rentalsbr☀ Bike Rentalsbr☀ Private Chefbr☀ In-home MassagebrbrbrGUEST ACCESS brbrThe driveway has room for 3 cars, and 1 additional car can park in the garage. There is also room for 2 more cars to park in a small parking lot across the street.brbrGuests will have access to all described rooms and amenities. The garage, as well as the washer/dryer located on the second floor, are available for guest use.brbrEach bedroom has its own window AC unit, and the third floor living area has two AC units to keep things cool on those hot summer days.brbrYou'll receive a code for the smart lock for secure and easy entrance into the home. 2 dog maximum, $250 pet fee applied to reservation.brbrOTHER THINGS TO NOTEbrbrDog Guidelines:brbr- We have wonderful neighbors and the last thing we want to do is disturb them. If we are alerted of excessive barking we will need to ask guests to remove the dog from the property for the remainder of the stay. Please do not book this property if your dog is known to bark excessively.brbr- By booking, you accept responsibility for any damage/extra cleaning your dog causes during the stay.brbr- No dogs left home alone, no exceptions.brbr- 2 dog maximum. One dog 40+ pounds allowed, or 2 dogs less than 40 pounds allowed. We cannot host pit bull breeds due to insurance restrictions. $250 pet fee applied to reservation.brbrOTHER DETAILS:brbr- We have an additional TopHost Vacation Rentals Guest Agreement separate from the booking platform. By booking this home, you agree to this process. The Guest Agreement is a legal document from our law firm that details the rules and policies for staying here.brbr- After you book, you'll receive a message with a link to the Rental Agreement. Please read it carefully and sign it to complete your booking. Signing this agreement is required for your stay in our home.brbr- Unexpected things can happen, so WE STRONGLY RECOMMEND getting travel insurance in case you need to cancel your booking.brbr- Our properties are always cleaned and turned over by highly rated, professional housekeeping companies.
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Bath 3

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Sleep 8

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Home Most popular vacation rentals in South Portland