Vacation Rentals By Owner In Southport, ME

$617.67

Waterfont Southport, Maine Cottage - Beautifully appointed 3-bedroom getaway

Southport, Maine, United States

Your cozy getaway awaits in Southport at this lovely house. With three bedrooms featuring two queen beds and a twin bed, there’s plenty of space for guests to relax. The three bathrooms add convenience for everyone in your group. A soothing office area includes a comfortable sofa bed, perfect for work or extra sleeping space. Heating keeps the atmosphere warm and inviting throughout your stay. Whether you’re unwinding after a day of exploring or enjoying quiet moments inside, this gorgeous home offers a peaceful retreat. We look forward to welcoming you to our place.

3

Bed

3

Bath

6

Sleeps

$127.36

/ Nightly

Apartment

New! Above garage loft style apartment!

Southport, Maine, United States

A modern, thoughtfully designed home offering comfort, style, and convenience. Ideal for solo travelers, couples, or business guests seeking a peaceful and well-appointed place to stay.brbrThe home features an open layout with plenty of natural light and high-quality furnishings throughout. A fully equipped kitchen makes it easy to prepare meals, while the living area provides a comfortable space to relax. The bedroom is designed for rest with a comfortable bed, fresh linens, and ample storage. A clean, modern bathroom includes essential toiletries for your stay.brbrGuests will have a private entrance to the apartment and shared outdoor space.brbrLocated in a quiet and safe neighborhood with easy access to local shops, restaurants, and nearby attractions. The area offers a calm atmosphere while still being conveniently close to everything you may need.brbrThis property is well suited for both short and extended stays. Whether you’re visiting for work or leisure, the home provides a relaxing retreat with all the essentials for a comfortable experience.brbrIMPORTANT:brInstead of placing a security deposit hold on your card, we include a small, non-refundable $25 damage waiver in the reservation total—so your funds remain available throughout your trip. This Waiver covers damages up to $300.br• Quiet hours are 9:00 PM – 9:00 AM. Please respect our neighbors at all times.br• Maximum occupancy is as shown on the listing. Additional guests are subject to $25/person/night and may result in cancellation if excessive.br• A mandatory, non-refundable damage waiver is included in your reservation total in place of a security deposit. Guests remain responsible for damage exceeding coverage or resulting from negligence or rule violations.br• Pets are not allowed at this property. Unauthorized pets may result in additional fees or cancellation. ADA Compliant Service Animals are permitted.br• No smoking or vaping anywhere on the property (indoors or outdoors).br• Open flames (fireplaces, fire pits, etc.) require prior written approval.br• No parties, events, or large gatherings without written approval.br• Waterfront/dock use (if applicable) is at your own risk and may require an additional waiver.

Bed

Bath

Sleeps

$261.43

/ Nightly

Apartment

Boothbay Open Plan 1- Bedroom Apt. Woods & Water. Southport.

Southport, Maine, United States

Located on Southport Island, we are near the water, and adjacent to Capitol Island. This detached garage apartment is spacious and great for couples or solo adventurers.brbrThis is an open plan apartment with kitchen, dining and living spaces connected. There is a private bathroom and one bedroom with a queen bed. We have a sofa and also a modern sofa bed/futon as well as an air mattress. We recommend that the additional sleeping accommodations be used for children or short term guests. We also have a pack-n-play crib available to renters.

Bed

Bath

Sleeps

$627.52

/ Nightly

Private Vacation Home

Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach

Southport, Maine, United States

Let it all go! Come here for peace and respite. Welcome to quintessential Maine summer living! Enjoy stunning ocean views and cool summer breezes at this very private and quaint seasonal home! This is a very comfortable, cozy, and classic retreat that is newly painted with new furnishings and is well appointed for your vacation needs. All bedrooms have new mattresses and bedding that will ensure a good night's sleep. Living room has a new large sectional. Linens and bath towels provided. Bring your own beach towels. Sip your morning coffee or have a picnic lunch in Adirondack chairs on the accessible rocky ledge. A covered deck offers shade without losing the sights and sounds of the coastal magic. Two chaise lounge chairs as well as two tables for outdoor eating are additional options for outdoor enjoyment. Four bicycles are available to be shared amongst guests at Cedarbush Stuga and our other vacation rental, Cozy Harbor Stuga. Please bring your own helmets. Beach chairs are available for guest use that are stored in garden shed.brbrWalk or bike to scenic Hendrick's Head Beach, a beautiful sandy beach with a small climbable outcrop called Kitten Island, in 5 minutes where you can swim, build sandcastles and explore tide pools at low tide. The Southport General Store, a local gathering spot with outdoor picnic tables, is also a 5 minute walk and offers not only breakfast pizzas, deli sandwiches and baked goods, but a carefully curated stock of hand-picked wines, beers, and ciders and more. For a leisurely wooded landscape walk, explore Hendrick's Head Preserve with an easy 1/2 mile loop for bird watching and nature photography. Shopping, restaurants, boat tours and more summer activities are a 12 minute scenic drive to Boothbay Harbor across the historic Southport Swing Bridge. A visit to the Coastal Maine Botanical Garden, the largest botanical garden in New England, is a must see as you will experience the exquisite beauty of Northern coastal horticulture and the giant trolls! brbrImportant Details:brCheck in 5:00PM. Strict check out at 10:00AM.brLinens and bath towels provided. brPlease bring your own beach towels. brbrOur property on Southport Island is exceptionally beautiful and is only 90 minutes from Portland. Come create memories at this spectacular setting. This is Maine at its best!

4

Bed

1

Bath

8

Sleeps

$1142.77

/ Nightly

Private Vacation Home

A SLICE OF HEAVEN | 4 Bed, 3 Bath

Southport, Maine, United States

Luxury Oceanfront Living on Southport IslandbrbrStep into a home that looks like it was plucked from the pages of a luxury coastal design magazine. A Slice of Heaven is a gorgeous, beautifully renovated oceanfront home located on the picturesque Southport Island. This incredible 3-bedroom, 3-bathroom retreat seamlessly blends the charm of its original early 1900s cottage roots with light, airy, high-end finishes, creating a breezy, chic, and ultra-convenient coastal haven. Rents Friday-Friday.brbr___________________________________________________brbrUnique and CharmingbrbrUnparalleled Ocean Views: Enjoy amazing views of the bold Atlantic Ocean, the entrance to Boothbay Harbor, and several iconic islands including Fisherman's, Ram, and Squirrel Islands.brbrHGTV Coastal Style: The interior boasts a light, airy coastal charm with tasteful renovations and high-end finishes throughout, providing a stunning and convenient layout.brbrMulti-Generational Convenience: With a full bedroom and bathroom located on the first floor, alongside all main living spaces, this home is exceptionally convenient for older guests, couples, and friends alike.brbrLuxurious Master Retreat: The upstairs water-facing master suite features a truly unique, open-air concept bathroom with three distinct areas (shower, soaking tub/vanity, water closet), plus a small private balcony offering a beautiful bird's-eye view of the water!brbrDiverse Outdoor Spaces: Choose your relaxation spot from the screened-in porch, the open deck, the downstairs covered patio, or the Adirondack chairs placed right out on the rocks, close to the surf.brbrBEDROOMS: (1) Queen, (1) Queen, (1) Twin and (1) KingbrBATHROOMS: (2) 3/4 bathroom with shower, (1) Full bathroom with shower and separate soaking tubbrbrDOGS ALLOWED Sorry, no pets are allowed at this homebrLINENS INCLUDED Yes, linens and towels are included in your reservationbrbrExplore Southport & Boothbay HarborbrSouthport Island is easily accessible via a bridge (no ferry needed!), offering the perfect balance of seclusion and accessibility to local attractions:brbrWalkable Gems: The Southport Library is a hidden gem and is within easy walking distance.brbrLocal Favorites: Drive a short distance to Robinson's Wharf for fresh seafood and classic Maine dining.brbrIsland Exploration: Explore the other side of the island with a visit to picturesque Hendricks Head Beach and the historic Southport General Store.brbrBoothbay Harbor Fun: Downtown Boothbay Harbor, with its vibrant shops, art galleries, and boat tours, is just a short drive away.brbr____________________________________________________________brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage. As Audrey puts it, “The home they stay in becomes a personality, a part of their lore, when a family connects with the right cottage. Whether they want a rustic cabin in the woods or a high-end ocean bungalow, the right setting sets the tone for the entire vacation.”brbrBook your luxury coastal retreat at A Slice of Heaven!

4

Bed

3

Bath

7

Sleeps

$875.6

/ Nightly

Cabin

Piffi Biff: Watch Whales & Lobster Boats from This Classic Oceanfront Gem!

Southport, Maine, United States

Piffi Biff: A Large Historic Home on Southport IslandbrbrWelcome to Piffi Biff, a stunning historic cottage perched on the rugged shores of Southport Island. This expansive home offers a front-row seat to the best of the Maine coast, featuring incredible views of the Atlantic Ocean, Squirrel Island, Burnt Island, and the bustling entrance to Boothbay Harbor. Whether you are watching a pod of porpoises or an endless parade of sailboats and lobster boats, Piffi Biff provides non-stop coastal entertainment.brbrCharming FeaturesbrClassic Maine Architecture: Experience the grandeur of a historic summer cottage featuring a spacious living room centered around a magnificent field-stone fireplace.brExceptional Ocean Views: Gorgeous vistas are the hallmark of this home, visible from the living room, dining room, breakfast room, and nearly every bedroom.brRoom for the Whole Family: With five bedrooms and a flexible layout, this home is designed for multi-generational gatherings and large groups.brIndoor-Outdoor Dining: Enjoy the salt air from the covered open deck, which serves as a secondary dining area and a peaceful spot to soak in the sights and sounds of the sea.brModern Conveniences: Piffi Biff boasts a washer and dryer—a rare and highly convenient feature for a historic home located so close to the water.brExpandable Living: For those hosting large dinners, the dining table includes an additional leaf to accommodate your entire group.brbrNOTE: Traveling with a very large group Piffi Biff can be rented alongside its neighbor, Pine Cliff Dweller, to create the perfect setting for a family reunion or multi-family vacation.brbrThe Details:brbrMinimum Stay: Weekly (Saturday-Saturday) from June through September; 4-night minimum available during the fall season. Stay for a week or longer during the shoulder season to receive a better value on your booking!brbrBEDROOMS: (2) King beds, (1) Queen bed, (1) Bedroom with three Twin beds, and (1) Bedroom with a single Twin bed.brbrBATHROOMS: (1) Full en-suite with shower, (1) Full bathroom with a soaking tub and separate shower, and (1) Half bath.brbrDOGS PERMITTED Up to two adult dogs are welcome here!brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrNature Watching: Keep your binoculars ready for whales, migratory shorebirds, and the local porpoise population right from your deck.brSouthport Island: Explore the quiet beauty of the island, including its historic bridges, local general store, and winding coastal roads.brBoothbay Harbor: Take a short drive into the harbor for world-class dining, boutique shopping, and boat excursions.brbrBook your historic island getaway at Piffi Biff today!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

Bed

Bath

Sleeps

$1035.5

/ Nightly

Private Vacation Home

Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens

Southport, Maine, United States

Only 12 minutes from Coastal Maine Botanical Gardens, home of Gardens Aglow. Welcome to this modern architectural gem tucked among the spruces on Southport Island, serenely peaceful and yet just a few minutes from Boothbay Harbor. The house is full of fun angles and expansive windows and is cantilevered over a granite ledge; think Frank Lloyd Wright meets Dr. Seuss.brbrThe house boasts two master suites (one 1st floor, one 2nd floor), a bunk room with five twin beds and a fourth Queen bedroom. There are three and a half luxurious baths.brbrIn June 2023 we completed a 18-month, down-to-the-studs renovation. Every surface is new for you to enjoy.brbrThe first floor -- kitchen, great room, a master bedroom with en-suite bathroom and a wrap-around deck with distant water views -- is accessible for anyone with mobility issues; there is just one small step to get in the house.brbrUpstairs there is laundry, a second master bedroom with an en-suite bathroom + its own private deck, a bunk room with five twin beds, a delightful bedroom for two and a shared bath off the hallway.brbrThe kitchen is fully equipped for cooking a feast and the dining table can seat 12.brbrThe house is fully air conditioned. Gas grill on the deck, lawn games including corn hole and a smokeless fire pit. Lots of outdoor seating on the various decks and around the fire. The property also has a lovely moss-covered forest that is the perfect spot for children to build fairy houses.brbrThe ocean is a short walk away, and you will have access to a delightful pebble beach.brbrSouthport is known for its peace and quiet, its bold oceanfront and proximity to the many restaurants, shops and galleries five minutes away in Boothbay Harbor. brbrSouthport also has its own sandy beach, three waterside restaurants, a lobster pound with seating right on the dock and a charming general store known for its wine selection and pizza.brbrHave kids Sign them up for a week of the youth Sailing Program at the Southport Yacht Club. Our kids do this and we can't recommend it enough!brbrWe are located 7 minutes from Boothbay Harbor, 10 minutes from the Coastal Maine Botanical Gardens and 5 minutes from Hendrick's Head Beach.

4

Bed

3

Bath

13

Sleeps

$494.18

/ Nightly

Private Vacation Home

Charming coastal retreat, sleeps 8 with Newagen Seaside Inn Amenities!

Southport, Maine, United States

Welcome to the Salty Dog Cottage… Located at the southern end of the island of Southport, our cottage provides everything you need to make life-long Mid-Coast Maine memories. This 3 bedroom, 1 bath cottage offers sleeping for up to eight. Downstairs you have a spacious bedroom just off the family room with a full queen; upstairs there is another spacious bedroom, also with a queen. The third bedroom offers 3 twin beds plus a twin trundle. Along with the 1 bath, our cottage also has a large outdoor shower, perfect for rinsing off after a long day on the water.brbrThe large front porch offers an inviting respite. Enjoy morning coffee as the sun comes up; meals under the stars at the large table; or simply sit and watch the goings-on in the neighborhood. Guests have access to all the amenities of Newagen Seaside Inn (NSI), including the swimming pool, tennis and basketball court, and for the adventurous, swimming in Newagen Harbor from the NSI dock. This is just a quick walk up the back path.brbrNSI also offers an award-winning restaurant and bar, perfect for those evenings you want someone else to do the cooking for you. Or shoot over to Robinson’s Wharf and grab some fresh seafood and fare of all types while you watch the local lobstermen bring in their catch.brStaying in Robinson’s also offers a full seafood market on site. Our cottage includes a propane grill and single stand burner for the do-it-yourself lobster lovers. The Southport General Store is just a few minutes up the road and offers everything else you need, including a deli and grill, pizzas, beer and wine, and an assortment of local treats.brThe rest of the island offers many options for exploration: walk the many local harbor communities; soak up some sun down at Hendricks Head beach; walk over to Town Landing and watch the comings and goings around Cuckold’s Lighthouse…the list goes on.brFeel like heading into town Boothbay Harbor is minutes away, offering shopping, dining, and entertainment in a historic seaside setting. For day trips, our location is ideal, offering a mid-point along Route 1, from historic Bath to Rockland, and all the quaint villages along the way (Wiscasset, Damariscotta, and Waldoboro). Make a day trip then return home to catch the sunset over at Sunset Path (located just across from the main entrance of NSI).brbrWe hope that you get the chance to make the lifelong memories here in Southport that our island community is known for.brbrIMPORTANT:brInstead of placing a security deposit hold on your card, we include a small, non-refundable $50 damage waiver in the reservation total—so your funds remain available throughout your trip. This Waiver covers damages up to $500.br• Quiet hours are 9:00 PM – 9:00 AM. Please respect our neighbors at all times.br• Maximum occupancy is as shown on the listing. Additional guests are subject to $25/person/night and may result in cancellation if excessive.br• A mandatory, non-refundable damage waiver is included in your reservation total in place of a security deposit. Guests remain responsible for damage exceeding coverage or resulting from negligence or rule violations.br• Pets are not allowed at this property. Unauthorized pets may result in additional fees or cancellation. ADA Compliant Service Animals are permitted.br• No smoking or vaping anywhere on the property (indoors or outdoors).br• Open flames (fireplaces, fire pits, etc.) require prior written approval.br• No parties, events, or large gatherings without written approval.br• Waterfront/dock use (if applicable) is at your own risk and may require an additional waiver.

3

Bed

1

Bath

8

Sleeps

$840.86

/ Nightly

Cottage

Waterfront Southport Cottage w/ Private Dock Quiet Coastal Retreat.

Southport, Maine, United States

Escape to the quieter side of coastal Boothbay Harbor at this classic waterfront cottage on beautiful Southport Island, just minutes from Boothbay Harbor. Thoughtfully maintained and full of traditional Maine charm, the cottage offers a peaceful setting for guests looking to slow down, relax, and enjoy life on the water.brbrLocated on a quiet dead-end street in a small waterfront neighborhood, the property is especially enjoyable in September, when warm days, cool evenings, lighter traffic, and calm harbor views create one of the most relaxing times of year to visit Maine’s coast.brbrThe cottage comfortably accommodates up to seven guests with four inviting bedrooms featuring one queen bed, two full beds, and one twin bed. One full bath and one half bath provide added convenience for longer stays. Two thermostatically controlled propane heaters keep the cottage warm and comfortable on cooler evenings while preserving the cozy feel of a traditional Maine waterfront home.brbrGuests can enjoy morning coffee overlooking the water, peaceful walks along the shoreline, nearby boating and Boothbay Harbor activities, fresh local seafood, and evenings with the windows open to cool ocean air. The private dock and waterfront setting make it easy to experience the natural beauty and slower pace that make Southport Island so special.brbrConveniently located near the Coastal Maine Botanical Gardens, downtown Boothbay Harbor, local restaurants, galleries, boat excursions, and scenic lighthouse tours, while still offering the privacy and quiet atmosphere many guests seek after the busy summer season.brbrFive-night minimum stay.brIdeal for adults and families seeking a peaceful coastal retreat.brReturning guests and longer September stays are welcomed.

Bed

Bath

Sleeps

$594.05

/ Nightly

Private Vacation Home

Southport ME Waterfront - Cozy Harbor

Southport, Maine, United States

Enjoy an island getaway on a private island off Southport, ME yet only 10 minutes to Boothbay Harbor. The house sits on an acre of waterfront property with views of cozy harbor. House comes with a private dock (seasonal) and 2 kayaks for your use. Master on first floor with King bed. Two additional bedrooms have a bunk and 2 twin beds. Enjoy a fully stocked kitchen so you can feel at home. Close to everything - Hendricks Head Beach, The Southport General store, restaurants, and Botanical Gardens.

Bed

Bath

Sleeps

$174.4

/ Nightly

Cottage

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Southport, Maine, United States

The Tan Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + restaurant across the street with 20 local lobstermen bringing in their catch. Small yard with picnic table & umbrella and out door chairs. Kitchen fully equipped, Free WIFI, cable TV, linens. Two miles from downtown Boothbay Harbor, shopping, boat rides, restaurants, & best Botanical Garden in the Northeast.

Bed

Bath

Sleeps

$174.4

/ Nightly

Cottage

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Southport, Maine, United States

The White Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + restaurant across the street with 20 local lobstermen bringing in their catch. Small yard with picnic table & umbrella and out door chairs. Kitchen fully equipped, Free WIFI, cable TV, linens. Two miles from downtown Boothbay Harbor, shopping, boat rides, restaurants, & best Botanical Garden in the Northeast.

Bed

Bath

Sleeps

$197

/ Nightly

Cottage

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Southport, Maine, United States

The Dockside Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + restaurant across the street with 20 local lobstermen bringing in their catch. Deck with picnic table & umbrella and out door chairs. Kitchen fully equipped, Free WIFI, cable TV, linens. Two miles from downtown Boothbay Harbor, shopping, boat rides, restaurants, & best Botanical Garden in the Northeast.

Bed

Bath

Sleeps

$268.29

/ Nightly

Cottage

One bedroom in United States of America, Southport

Southport, Maine, United States

Tucked away on Southport Island is this little guest house for two. Located just across the swing bridge from Boothbay Harbor, Little Nick offers one bedroom, a bright and sunny living area, galley style kitchen, and a deck with peeks of the water.brbrDowntown Boothbay Harbor is just a 7-minute drive away. Robinson`s Wharf is right around the corner where you can experience fresh seafood and live music on Sundays. Periwinkle Cottage is located next door to Little Nick. Perfect for two couples who would like to travel together but have their own place! brbrDogfish Head Beach is 3 1/2 miles away. The Coastal Maine Botanical Gardens is a quick 10-minute drive, and laundry is located 3 miles away.brbrGuests have access to the entire cottage. Please note this cottage does not have cable TV but does have a TV that can connect to your Netflix account.brbrIMPORTANT:brInstead of placing a security deposit hold on your card, we include a small, non-refundable $25 damage waiver in the reservation total—so your funds remain available throughout your trip. This Waiver covers damages up to $300.br• Quiet hours are 9:00 PM – 9:00 AM. Please respect our neighbors at all times.br• Maximum occupancy is as shown on the listing. Additional guests are subject to $25/person/night and may result in cancellation if excessive.br• A mandatory, non-refundable damage waiver is included in your reservation total in place of a security deposit. Guests remain responsible for damage exceeding coverage or resulting from negligence or rule violations.br• Pets are not allowed at this property. Unauthorized pets may result in additional fees or cancellation. ADA Compliant Service Animals are permitted.br• No smoking or vaping anywhere on the property (indoors or outdoors).br• Open flames (fireplaces, fire pits, etc.) require prior written approval.br• No parties, events, or large gatherings without written approval.br• Waterfront/dock use (if applicable) is at your own risk and may require an additional waiver.

Bed

Bath

Sleeps

$1210.61

/ Nightly

Private Vacation Home

Water`s Edge on Pratts Island

Southport, Maine, United States

Experience ultimate relaxation in this spacious and tranquil oceanfront retreat, located just minutes from Boothbay Harbor`s fine dining, scenic hiking trails, shopping, and vibrant downtown.brbrInside, enjoy the home`s stunning craftsmanship featuring vaulted ceilings, hardwood floors, stainless steel appliances, granite countertops, oversized picture windows, a TV, and a beautiful granite stone fireplace. The main house offers a primary bedroom and full-sized ensuite bathroom on the first floor, as well as a half bath. The second floor has three additional bedrooms: one with queen & twin, one with two twins, and one with a queen. Both a Keurig coffee maker and a regular drip coffee marker are available. brbrIn addition, the property includes a cozy loft apartment (The Annex) with a king-sized bed, private bathroom, and a balcony overlooking the water. A separate bunkhouse provides extra space with two sets of bunk beds and an outdoor shower. Please note that wifi is unavailable in The Annex and The Bunkhouse. brbrOutside, the property offers a sprawling oceanfront lawn, a shared dock, and an array of amenities, including a whiffle ball field, volleyball net, ping pong table, ample seating areas, patio furniture, an outdoor dining space for four. If you have a kayak or canoe, feel free to launch it right here! Don’t have one Ask us for a referral to our trusted local vendor. We often suggest Maine Kayak, located in Boothbay Harbor for this.brbrThe dock and float are shared with 3 other neighboring homes. If you use our mooring as the boat can not be tied to the dock except for unloading and loading please be sure you have your own transportation to get to your boat. All kayaks and canoes need to be tied and in the water and not on the dock. brbrPlease contact the property manager before considering this property for any events. brbrIMPORTANT:brInstead of placing a security deposit hold on your card, we include a small, non-refundable $100 damage waiver in the reservation total—so your funds remain available throughout your trip. This Waiver covers damages up to $1,000.br• Quiet hours are 9:00 PM – 9:00 AM. Please respect our neighbors at all times.br• Maximum occupancy is as shown on the listing. Additional guests are subject to $25/person/night and may result in cancellation if excessive.br• A mandatory, non-refundable damage waiver is included in your reservation total in place of a security deposit. Guests remain responsible for damage exceeding coverage or resulting from negligence or rule violations.br• Pets are not allowed without prior approal and non-refundable pet rent.br• No smoking or vaping anywhere on the property (indoors or outdoors).br• Open flames (fireplaces, fire pits, etc.) require prior written approval.br• No parties, events, or large gatherings without written approval.br• Waterfront/dock use (if applicable) is at your own risk and may require an additional waiver.

6

Bed

3

Bath

14

Sleeps

$704.65

/ Nightly

Private Vacation Home

Colburn Cottage - Whole Home

Southport, Maine, United States

Perfect Family Vacation Spot on Capitol Island – Spacious Waterfront Retreat!brbrGather your loved ones and escape to this ideal family getaway on Capitol Island in Southport, where coastal charm meets comfort and space. Nestled in a peaceful private island community, this spacious home offers everything you need for a relaxing and memorable vacation.brbrStep outside and discover a small, sandy beach right at your doorstep during low tide—perfect for beach-combing, wading, and enjoying the serene shoreline. The level lawn provides ample room for outdoor games, picnics, or simply soaking in the sunshine.

7

Bed

1

Bath

12

Sleeps

$332.23

/ Nightly

Cottage

Colburn Cottage - Downstairs - Waterfront + Beach!!

Southport, Maine, United States

Perfect Family Vacation Spot – Beachfront Bliss!brbrThis charming seaside retreat offers everything you need for a relaxing and memorable vacation. The inviting space features two bedrooms, a three quarter bathroom, and comfortably sleeps up to four guests—perfect for a small family or couple’s escape. Step right outside to a small, sandy beach just at your doorstep—perfect for sandcastle building, swimming, or soaking up the sun.brbrThe level lawn provides plenty of open space for lawn games, picnics, or simply enjoying the ocean breeze or watching family play on the lawn. Take in the breathtaking views of the outer ocean and nearby islands, whether you’re sipping coffee in the morning or watching the sunset in the evening.

2

Bed

4

Sleeps

Exceptional(1)

$227.79

/ Nightly

Apartment

Ticket Office: Traveler’s Quaint Coastal Retreat

Southport, Maine, United States

Situated in the heart of midcoast Maine, the “Ticket Office” is the perfect stay for a quick coastal stay. This tiny house provides a unique blend of modern comfort, new amenities, and New England charm. Local seafood restaurants and attractions are within a quick drive - or even walk - ensuring that you have a memorable stay. Spend time in the harbor experiencing the breathtaking beauty of a breezy coastal summer day. We invite you to relax and unwind at the “Ticket Office”.

Bed

Bath

Sleeps

$260.51

/ Nightly

Cottage

Enjoyable 1-bedroom rustic cottage in Southport.

Southport, Maine, United States

Get ready to relax in this welcoming 1-bedroom rustic cottage in Southport. This gorgeous retreat features a cozy queen bed, a charming living room with a comfy futon, and a full bathroom stocked with Linens. Guests can enjoy the peaceful surroundings and unwind in this wonderful hideaway. Experience the magic of Southport at our cottage.

1

Bed

1

Bath

4

Sleeps

Select Dates for Price

Private Vacation Home

Southport Island Escape: Walk Right Off the Deck onto Your Private Dock - Stunning Water Views!

Southport, Maine, United States

NEW FOR 2026!brbrGriffin Cottage: Classic Maine Summer Home on Southport IslandbrbrStep back in time while enjoying modern luxury at Griffin Cottage, a gorgeous classic Maine summer home located on beautiful Southport Island. Situated just across the bridge from the bustling energy of Boothbay Harbor, this exceptional property offers an unparalleled waterfront experience. Defined by its authentic charm, breathtaking views, and rare direct dock access, Griffin Cottage is the perfect setting for a truly relaxed coastal retreat.brbrCharming FeaturesbrWalk-On Dock & Float: The centerpiece of this property is the incredible private pier and float system attached directly to the deck. You can walk right off your living space and onto the water—perfect for sunbathing, swimming, or launching your kayaks.brIncredible Water Vistas: The home boasts expansive, panoramic views from the spacious deck and numerous interior rooms, capturing the quiet beauty and activity of the Midcoast Maine shore.brExclusive Island Location: Experience the peaceful, traditional atmosphere of Southport Island, known for its rugged beauty and slower pace of life.brReal Maine Charm: Griffin Cottage maintains the character and simple elegance of a traditional coastal home, blending historic soul with the comforts needed for a modern vacation.brSpacious Living: With three bedrooms and room for up to six guests, there is plenty of space for the whole family to gather and make memories.brbrNOTE: Southport is connected to the mainland by a historic swing bridge, giving you the secluded feel of island living with the convenience of being just minutes away from downtown activities.brbrThe Details:brbrMinimum Stay: Weekly, Saturday-Saturday.brbrBEDROOMS: (1) Queen, (1) Queen, (2) TwinsbrbrBATHROOMS: (1) Full bathroom with shower on main level, (1) half bathroom upstairsbrbrDOGS PERMITTED No, pets are not allowed at this home.brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrHendricks Head Lighthouse: Located at the southern tip of the island, this is a must-visit spot for iconic photos and beachcombing.brRobinson’s Wharf: A classic Maine lobster wharf is just a short trip away, offering the freshest seafood in a casual, waterfront setting.brDowntown Boothbay Harbor: Take a quick drive across the bridge to explore unique shops, art galleries, and major boat tours.brBoothbay Region Land Trust: Discover nearby hiking trails that wind through the woods and along the rocky coastline for spectacular views.brbrBook your unforgettable stay at Griffin Cottage today!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

3

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Southport, ME

$617.67

$127.36

$261.43

$627.52

$1142.77

$875.6

$1035.5

$494.18

$840.86

$594.05

$174.4

$174.4

$197

$268.29

$1210.61

$704.65

$332.23

$227.79

$260.51

Most popular vacation rentals in Southport

$1417.00

$197.00

$227.79

$260.51

$450.25

$499.38

$587.51

$1210.61

$594.05

$1347.00

Most Popular Cities in Maine