Vacation Rentals By Owner In Southport, ME

Showing 48 Of 48 Vacation Rentals

$1248.55

CLIFF COTTAGE | TOWNSEND GUT | 4 Bed, 2.5 Bath

Southport, Maine, United States

Cliff Cottage: Historic Charm on Townsend GutbrbrWelcome to Cliff Cottage, a beautifully remodeled retreat perched above the scenic Townsend Gut on the northern tip of Southport Island. This cottage chic home masterfully blends old-world Maine charm — hardwood floors, wooden cabinetry, and expansive windows — with modern luxury. Located on a quiet stretch of the island, Cliff Cottage offers a front-row seat to the parade of wildlife, sailboats, and lobster boats navigating the Gut.brbrCharming FeaturesbrTownsend Gut Waterfront: Set high with dramatic views, the large waterside deck is the perfect spot for morning coffee as the sun rises or dinner under the stars.brWildlife Watching: Keep your binoculars handy! You’ll likely spot seals, seagulls, osprey, and eagles right from the deck or the dock.brMaster Suite Sanctuary: The main level features a spacious master king suite with a private en-suite bathroom and a cozy, private sitting room located between the bedroom and the living area.brModern Open Concept: The main floor flows seamlessly between the living, dining, and kitchen areas, all featuring comfortable, well-coordinated decor and huge windows to pull the view inside.brPrivate Dock & Float: Why not try fishing off the dock or enjoying cocktails in the chairs at the head of the pier as the sun sets brSpacious Accommodations: With four bedrooms across two levels, there is plenty of room for up to eight guests to relax in style.brbrNOTE: To ensure the best experience and safety given the home's layout and waterfront positioning, Cliff Cottage is not recommended for children under 10.brbrThe Details:brbrMinimum Stay: Weekly, Saturday-Saturday.brbrBEDROOMS: (2) Kings, (1) Queen, (2) TwinsbrbrBATHROOMS: (1) Full with tub/shower combo, (1) Full with jetted tub and separate shower, (1) Half bathbrbrDOGS PERMITTED No, pets are not allowed at this home.brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrLocal Dining: Walk or take a short drive to Robinson’s Wharf for fresh seafood or enjoy an award-winning meal at the Newagen Inn.brSouthport Staples: Visit the Southport General Store for local treats, pizza, and wine, or soak up the sun at Hendricks Head Beach.brDowntown Boothbay Harbor: Just minutes away, you’ll find eclectic shopping, fine dining, and historic seaside entertainment.brIdeal Day Trips: Use Cliff Cottage as your home base for exploring Route 1—from the historic maritime city of Bath to the picturesque harbors of Rockport, Wiscasset, and Damariscotta.brbrBook your historic Maine getaway at Cliff 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.

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$554.09

/ Nightly

Private Vacation Home

NEW FOR 2024 | SEA MIST | 4 Bed, 1 Bath

Southport, Maine, United States

Sea Mist: A Coastal Haven on Capitol IslandbrbrExperience the quintessential charm of Maine with a stay at Sea Mist. Nestled on the picturesque Capitol Island -- drivable from town, and just off the shores of Southport Island -- this delightful cottage invites you to savor the true essence of coastal living. Wake up to breathtaking ocean views and the soothing sounds of the waves from this idyllic oceanfront retreat, where you can stroll along the shared beach, launch a kayak in the protected cove, or simply soak up the sun and fresh salt breeze. Capitol Island is a wonderful place for walking and beachcombing, offering a small-island feel while remaining conveniently close to the amenities of Southport and Boothbay Harbor.brbrCharming FeaturesbrOceanfront Bliss: Enjoy a front-row seat to the tides from this classic cottage. The proximity to the water makes it easy to enjoy the sights and sounds of the Maine coast throughout your stay.brCapitol Island Charm: Connected to Southport by a short bridge, Capitol Island offers a unique, tranquil environment with a sense of privacy and old-world coastal character.brKayaker’s Paradise: The protected cove surrounding the island is ideal for kayaking, paddleboarding, and exploring the shoreline at your own pace.brCozy Coastal Atmosphere: Sea Mist is a warm and inviting space, perfect for reconnecting with family and friends in a quintessential summer cottage setting.brOutdoor Relaxation: Unwind on the porch and take in the panoramic views, or enjoy leisurely walks along the community's quiet lanes and shared beach areas.brbrThe Details:brbrMinimum Stay: Weekly stays (Saturday-Saturday) during the Summer season; 4-night minimum available in the Fall. Stay for a week or longer in the Fall to receive a better value on your booking!brbrBEDROOMS: 4 Bedrooms featuring (4) Double beds.brbrBATHROOMS: (1) Full bathroom with shower.brbrDOGS PERMITTED Yes! Up to two adult dogs are welcome to join you on your adventure.brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrCapitol Island Beaches: Enjoy access to shared community beaches, perfect for sunbathing, swimming, or building sandcastles.brSouthport & Beyond: Explore the nearby Hendricks Head Lighthouse or stop by the Southport General Store for local treats and essentials.brBoothbay Harbor: A short drive takes you into the heart of the harbor for world-class dining, shopping, and boat tours.brBiking the East Side: For those bringing bikes, the east side of Boothbay Harbor offers the most scenic and bike-friendly roads in the area.brbrBook your island escape at Sea Mist 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.

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Exceptional(25)

$870.44

/ Nightly

Country House

Saltwater farmhouse on 2+ acres of waterfront with private dock

Southport, Maine, United States

Hartwell House has origins in the 1770s and expanded in the 1800s and 1970s. It is in a protected cove off Ebenecook Bay with deep water accesss for all water activities. Located on the fully contained community of Southport Island and accessible via a bridge. Hartwell House is within 15 minutes of its more famous, and oft times more 'busy' neighbor, Boothbay Harbor. In addition to a private dock, the house offers:brbr. An immense living/family room with fireplacebr. A charming country eat-in kitchen with fireplacebr. Cable and high speed internetbr. A well planted patio on a sweeping front lawn that edges the covebr. Many edible offerings from the blueberries, raspberries, rhubarb, apples and grapes that grow on the property (While edibility depends on when you are there, the beauty of the growth is constant)brbrbrPets on a case by case basisbrbrKayaks available for your use

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Exceptional(5)

$279.2

/ Nightly

Cottage

Charming 3-bedroom cottage in Southport with water views and close to Boothbay.

Southport, Maine, United States

Escape to a fabulous 3-bedroom cottage in Southport. This welcoming retreat features a queen bed, bunk bed, twin bed, and king bed, perfect for a cozy getaway. With amenities like WiFi, a washing machine, heating, and AC, guests can relax and unwind. The three bathrooms offer a bathtub for a soothing soak after a day of exploring. brbrOutside you'll enjoy a near-wrap around deck with fire feature and direct views of Christmas Cove, an inlet with direct access to the Atlantic Ocean. A manicured path off the driveway leads to the waterfront street where a cozy bench and kayaks await you. Close to the great coastal town of Boothbay but secluded at the end of a long private driveway. Fall in love with Southport and enjoy the magic it has to offer.

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Exceptional(8)

$638.42

/ Nightly

Private Vacation Home

Oceanfront home

Southport, Maine, United States

Beautiful oceanfront home with large outdoor deck facing the water for dining and relaxing, Great sunsets. Private sandy beach close.brDock and kayaks available. brNear Boothbay Harbor for dining, shopping and boat excursion. Hop a ride to Monhegan Island for the day. Boothbay Gardens 10 minutes away.

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Exceptional(39)

Select Dates for Price

Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck

Southport, Maine, United States

Island PinesbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrTucked away in a private setting and surrounded by two acres of Maine forest, this charming, two-story vacation rental is the perfect home-away-from-home for your next getaway to Southport Island. Bright, pristine, and newly-built, this four-bedroom home features vaulted ceilings, comfortable furnishings, and more than a few nods to the great state of Maine with its decor and artwork. The open floor plan includes a well-equipped, island kitchen with stainless steel appliances, a large dining table with seating for eight, and a cozy living area with a Netflix-ready flatscreen TV. Outside, enjoy the sights and sounds of the woods from the furnished deck where you can socialize or fire up the grill and dine in the open air. And when it's time to call it a night, you'll find four comfortable bedrooms here including one king suite, two rooms with queen-size beds, and a kids' room with two twin bunks.brbrWhat's nearby:brThis home is within walking distance of Cozy Harbor and only a mile from Hendricks Head Lighthouse and the adjacent beach area offering terrific views and opportunities to swim in the cool waters and catch tiny crabs in the seaweed. Just a few miles northeast, check out bustling Boothbay Harbor with its many attractions and water activities. Grab a bite to eat from Robinson's Wharf offering terrific seafood, an oyster bar, and wonderful views of the cove. And if you need to stock up on essentials during your stay, the eclectic Southport General Store is less than a half-mile north of this home.brbrThings to know:brFree high-speed WiFibrUp to two family dogs (20 lbs. max.) are welcomebrBooster seat, Pack-N-Play, and baby gates are providedbrIncludes a selection of yard gamesbrA 4x4 is recommended in winterbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.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.

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Exceptional(19)

Select Dates for Price

Beachfront Delight with detached guesthouse, private beach access, Dog-friendly

Southport, Maine, United States

Deep Cove CabinbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled on the Sheepscot River, this house and detached guest home boast a stunning waterfront location! A private beach makes it easy to enjoy tide pools and sunsets. Enjoy water views from nearly every room. Gather on the riverside deck to share alfresco meals or admire breathtaking sunset views over the water. The desirable location is just a short walk away from the Hendricks Head Lighthouse and Preserve.brbrA wood-burning fireplace creates inviting allure in the main house's living area. Relax on down-filled sofas and cast your favorite apps. On quiet afternoons, select a book from the well-stocked shelves. Whip up delicious dishes in the kitchen, appointed with an array of helpful gadgets. You'll find two tables in the dining area.brbrThe primary bedroom holds an L-shaped desk for a convenient workspace.brbrThe guesthouse has large windows that provide excellent views of the river in the living area. Handy highlights of the kitchenette include a mini-fridge, a two-burner electric stove, and an instant kettle. Sip coffee at the small table. There is a sleeping area and a bathroom with a walk-in shower.brbrKick back with crisp drinks on the guesthouse deck. Follow the stone pathway to the water's edge.brbrTHINGS TO KNOWbrAccess to the front door is via three exterior steps and an unlevel stone pathway through the yard. brThis property does not have air-conditioning.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 3 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Select Dates for Price

Stunning oceanfront cottage w/ private deck and Atlantic views

Southport, Maine, United States

Serene Newagen HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrMarvel at breathtaking oceanfront views of Cape Harbor, Cape Island, and the Atlantic Ocean at this stunningly situated Southport home. This property sits at the end of Gray Road (which is shared with only a handful of other homes), ensuring that your stay will be quiet and serene. Spend your afternoons upstairs on the private deck overlooking the water, reading and relaxing downstairs with a wall of windows to frame the view, and entertaining friends and loved ones in the open kitchen and living area.brbrWhat's nearby: brThis oceanfront home sits on the edge of Cape Harbor, six miles south of bustling Boothbay Harbor. When you're in town, you can sample tasty lobster rolls from Shannon’s Unshelled and stroll across the longest wooden footbridge in the United States. Back at the house, when you're not walking to the local library, you'll be just over two miles from a delicious lunch at Oliver's on Cozy Harbor Wharf and three miles south of Hendricks Head Lighthouse.brbrThings to know:brFree WiFibrFull kitchenbrOne of the listed twin beds is a trundlebrThe owner sometimes uses the apartment over the garage but does not interact with guestsbrbrParking 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.

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Most popular vacation rentals in Southport

$1417.00

/ Nightly

Cottage

Ocean front cottage on a drive-on island in Boothbay Harbor, Maine

Southport, Maine, United States

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$197.00

/ Nightly

Cottage

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

Southport, Maine, United States

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$227.79

/ Nightly

Apartment

Ticket Office: Traveler’s Quaint Coastal Retreat

Southport, Maine, United States

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$260.51

/ Nightly

Cottage

Enjoyable 1-bedroom rustic cottage in Southport.

Southport, Maine, United States

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$450.25

/ Nightly

Cottage

Cottage at Island Point; Charming Coastal Retreat

Southport, Maine, United States

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$499.38

/ Nightly

Cabin

Oceanview Cabin Retreat in Southport

Southport, Maine, United States

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$587.51

/ Nightly

Private vacation home

Decker Cove Southport Paradise with Central Air Conditioning

Southport, Maine, United States

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$1210.61

/ Nightly

Private vacation home

Water`s Edge on Pratts Island

Southport, Maine, United States

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$594.05

/ Nightly

Private vacation home

Southport ME Waterfront - Cozy Harbor

Southport, Maine, United States

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$1347.00

/ Nightly

Private vacation home

Miradon Ocean Estate: Expansive Ocean Views

Southport, Maine, United States

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Vacation Rentals By Owner In Southport, ME

$1248.55

$554.09

$870.44

$279.2

$638.42

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

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