Southwest Harbor Vacation Rentals
Southwest Harbor Vacation Rentals & also vacation rentals in Bass Harbor, Bar Harbor, Northeast Harbor, Blue Hill, Trenton & all the villages of Mount Desert island & Acadia National Park.
Oceanfront & lakefront cottages, cabins, condos, villas, and estates. For more details and availability, just click on the listings below.
Many Pet Friendly Vacation Rentals! Just look for the running dog.
Most rentals go from Saturday to Saturday. Check in: 3 PM-- Check out: 10 AM unless otherwise stated. Most Listings have 2 photos and a detailed description with prices. Although these pages are frequently updated, please check with our office to confirm current prices & availability
Page 4 of 5, showing 20 records out of 88 total, starting on record 61, ending on 80
Accommodations For 6
Harbor Breeze WW Unit #9 (SW06-P2)
10 Robinson Lane, Southwest Harbor
Area: Ocean Front, Water View, Mountain View, In Town, Water Access
Lovely waterfront condominium complex located at the head of Southwest Harbor with sweeping, unobstructed views of the harbor. Freshly painted in 2023, this unit is conveniently located within easy walking to town & shopping. It is also close to Acadia National Park's hiking trails, carriage roads and scenic roadways. A free Island Explorer bus stops on the road in front of the building. Guests have use of a heated outdoor swimming pool and shared private dock. NOTE: Interiors completely freshened with new paint in 2023.
Accommodations For 7
Harbormasters House (SW07-S1)
98 Clark Point Road, Southwest Harbor
Area: Ocean Front, Water View, In Town, Water Access
Historically known as the Harbormaster’s House, 98 Clark Point Road was originally built in 1888 with a major renovation in 1989. This venerable property is located along the shores of the Great Harbor and enjoys captivating harbor views of all the marine activity. A one car attached garage allows direct access to the house. And, a meandering path through lovely perennial gardens leads to the shore. Guests can enjoy the private, newly renovated and expansive waterside deck of 40‘ x 25 feet with its own private boathouse and four cozy Adirondack chairs. The deck sits in the water for mid and high tides and invites kayakers and paddle boarders (easily rented nearby) to launch off the beach in lower tides. The boathouse invites you to read, nap, have cocktails or just take in the sights and sounds of the Harbor. Close to town for dining and shopping as well as a convenient spot to catch the free Island Explorer bus. **The dock in photos is no longer there.
Greendays (SW07-K1)
16 Town Wharf Way, Southwest Harbor
Area: Ocean Front, Water View, Mountain View, Rural, Water Access
SUNDAY TO SUNDAY RENTAL - HOWEVER CALENDARS WILL DISPLAY SATURDAY TO SATURDAY DATES A classic shingled oceanfront cottage located right on the water with deep water dock access. A spacious and comfortable interior with large stone fireplace for cool evenings, as well as an ocean facing deck for relaxing. Greendays is a great choice for those seeking a wonderful oceanfront experience, all within an approximate 15 minute walk to the center of town for shopping and dining as well as a great spot to catch the free MDI Explorer Bus!
Accommodations For 8
Meadowside Cottage (SW06-G1)
323 Seawall Road, Southwest Harbor
Area: Rural
Great home with large private yard that offers lots of activities badminton, hammock, fire pit and gardens. Close proximity to Cable Crossing beach (approximately 2/10th of a mile) as well as the picnic area at Seawall for a lovely ocean side picnic. This cottage is also convenient to town for dining and shopping.
Pine Knoll (SW08-H8)
35 Sail Mountain Road, Southwest Harbor
Area: In Town, Rural
This location has it all for those looking to be near park trails and town, and still maintain a private setting when they return home for the day. Set atop Sail Mountain, Pine Knoll is spacious and bright, offers air conditioning, a large deck, a hot tub and a lovely wooded setting with granite outcroppings. Inside windows abound bringing in the natural light, and the floor to ceiling hearth with propane fireplace makes a nice centerpiece for the main living space. There is a dining area (seats 8) adjacent to the eat-in kitchen which is well equipped and airy with open shelving.
Blueberry Lane Cottage (SW08-K3)
16 Blueberry Lane, Southwest Harbor
Area: Rural
Charming and comfortable new cottage ('10) with extended views of the blueberry fields and Beech Hill Mountain. This home is very warm, comfortable and filled with light from the abundance of windows. Located in a peaceful quiet area close to Long Pond for boating and hiking and Echo Lake for a day at the beach. The perfect place to spend your Maine vacation!
Thalassa Point (SW08-M5)
Seawall Road, Southwest Harbor
Area: Ocean Front, Water View, Rural, Water Access
Amazing water front cottage tucked into the woods just steps from the ocean. Offering dramatic views from the upper and lower decks, this private home is the perfect place to spend your Maine vacation. This home has a lot of natural light from the abundance of windows and in the summer, there is a beautiful perennial garden for your enjoyment. One can also enjoy the large lawn area for some outdoor activities, as well as the easy access to the Seawall rocks for a lovely ocean front picnic.
Vafiades Diaz House (SW08-V1)
Lawler Lane, Southwest Harbor
Area: Water View, In Town
Large home overlooking Southwest Harbor on dead end street in a central location. Right of way path to the shore just 20 yards from the house. Within walking distance of shops and restaurants. Minutes from Acadia National Park.
Mendelson Log Cabin (SW08-M3)
38 Dirigo Road, Southwest Harbor
Area: In Town, Rural
Charming log cabin set in a quiet, residential location on the Dirigo Road. This 3 bedroom, 2 bath home has a large wrap around deck and a small yard in the rear. East proximity to town and the harbor as well.
Fox Run (SW08-B1)
15 Kinfolk Lane, Southwest Harbor
Area: In Town
Fox Run is a private 4 season Contemporary style home that sits on a partially wooded lot surrounded by native Maine plantings. The home is filled with lots of natural light and is conveniently located just outside of town center, making this property the perfect spot to spend your Maine vacation. Fox Run is located in a quiet neighborhood on Kinfolk Lane that is within an easy walk to town (approximately 5/10th of a mile) where one can shop, dine or grab the free Island Explorer bus. This property is also within close proximity to the Great Harbor Marina and all that MDI & Acadia National Park have to offer. Fox Run is a large home with 4 bedrooms and 3 1/2 baths - plenty of room for everyone and then some! Enjoy morning coffee on the wrap around deck, which overlooks the expansive back yard and offers a peak-a-view of the ocean through the trees. There is also wonderful screened porch with additional seating and a dining table located right off the kitchen.
The Wood Box (SW06-C4)
53 Seawall Road, Southwest Harbor
Area: Ocean Front, Water View, In Town, Water Access
Formerly listed with us as “Woodhaven,” The Wood Box has had some recent renovations. This summer cottage has been in the same family since it was built in 1932. Situated directly on the shore with a stone patio on the water side, The Wood Box has full views of the mountains and the water. Close proximity to downtown for dining and shopping.
The Roost (SW08-G2)
19A Winding Lane, Southwest Harbor
Area: Water View, Mountain View, Rural
The Roost, built in 2000 and renovated in 2014, combines rustic style with contemporary use of space and conveniences. It has outstanding views from the upper deck of the Somes Sound, mountains of Acadia and outlying islands. Located in a quiet residential area, yet close to local amenities. An easy walk will take you to center of the village, to the town docks or quiet lanes that lead you across the causeway to golf course and access to the trails of Acadia National Park. Decks on both the main level and the second level master bedroom.
Quietside Retreat at 264 Main (SW08-T1)
264 Main Street, Southwest Harbor
Area: In Town
SUNDAY TO SUNDAY RENTAL This charming Cape Cod style home was completely renovated during the winter and spring of 2014. Be one of the first to enjoy all that it has to offer! Located very near the center of Southwest Harbor's bustling village, Quietside Retreat combines older charm, new amenities, updated spaces, and Island-wide access-- a winning combination!
Herrick Road Home (SW08-M4)
83 Herrick Road, Southwest Harbor
Area: In Town
SUNDAY TO SUNDAY RENTAL - CALENDARS WILL REFLECT SATURDAY TO SATURDAY. Freshly remodeled and updated, you will find this lovely property located in the Clark Point Road neighborhood in Southwest Harbor, within easy walking distance (approximately 3 blocks) to town center in one direction and the working harbor in another. The front yard, deck, and front rooms offer views of the neighborhood, the Western Mountain cluster, while the brick terrace with dining table that seats eight and fire pit enhance the secluded, quiet rear garden. Sound-insulated interior walls and floors provide quiet space separation and privacy. And child-friendly design provides an engaging and safe environment for children. Catch the free Island Explorer bus in town for a day of exploring around Acadia National Park / MDI without having to worry about parking or traffic.
Causeway Cottage (SW08-H1)
17 North Causeway Lane, Southwest Harbor
Area: Water View, Mountain View, In Town
Charming, private light filled cottage located off desirable Fernald Point Road, next to the Causeway Club. Inside you will find plenty of room for everyone to enjoy their Maine vacation. The open floor plan boasts a sky light in the living room, lots of light filled windows through out, wood floors (downstairs) as well as beautifully crafted, vaulted wood ceilings. Enjoy the comfort of the screened in porch or the lovely sunny deck, both of which look towards the golf course and peaks of Norwood Cove. For the hiker, The Causeway Cottage is close proximity to Flying Mountain, Valley Cove, Acadia Mountain, just to name a few, and is also an easy drive into town for your dining and shopping needs. Bar Harbor is also a 25 - 30 minute car ride.
Dir Treu (SW08-M1)
50 Shore Road, Southwest Harbor
Area: Water View, Mountain View, Rural
Spacious home with spectacular view of the harbor, the mountains and islands. Located across the road from the Manset town dock, this home offers spacious comfortable living with a wrap around deck to enjoy the view. A smaller cottage in front of this home can be rented with this home for a family reunion or vacationing with friends. With lots of amenities and tasteful furnishings "Dir Treu" is an ideal vacation home for you and your family.
Accommodations For 9
Tide Down (SW09-S2)
7 Harbor Ave, Southwest Harbor
Area: Water View, In Town
Enjoy lovely peaks of the water from this 4 bedroom, 2 bath house situated on an in-town picturesque side road that ends at a harbor overlook. Decks on the ground and second level allow for outdoor seating and entertaining. For the sailors or adventurers there's an outdoor shower, too.
Accommodations For 10
The Sheilin aka Johnston Cottage (SW09-J1)
65 Route 102A, Southwest Harbor
Area: Ocean Front, Water View, In Town, Water Access
Located on the Manset shore, this lovely rustic open beam cottage with a fireplace in the living room, offers plenty of room for a large family vacation. From the living room and deck you overlook the Great Harbor with extended views up Somes Sound, outlying islands and the mountains of Acadia. A great place for canoeing and kayaking. Also within walking distance to town and the FREE Island Explorer shuttle bus.
Aleria (SW10-M1)
16 Kinfolk Cottage, Southwest Harbor
Area: In Town
A beautiful and charming 100 year old cedar shingled "Captains House" with covered granite porch and large open yard situated on a quiet dead end road. Easy walk to the center of town, the park or the ocean. Offering a spacious yard and comfortable rooms centered around a large fireplace in the living room and a modern kitchen. A wonderful summer house for your Maine vacation that can accommodate 2 families.
Harbor View Cottage (SW10-H2)
90 Clark Point Road, Southwest Harbor
Area: Ocean Front, Water View, In Town, Water Access
This 1930 built home has been fully renovated in 2018 by the new owners. Everything is new - kitchen, bathrooms, floors, paint, etc. The house is ideally situated in town and on the water with shore access. Acadia National Park is accessible by car or free Island Shuttle Bus. The property is composed of the main house and guest house. Walk to town for ice cream or a popover. Walk to Beal's for a lobster. Launch your kayak from the house. Sit on the large deck and watch the lobster boats come and go. Take in a magnificent sunset and relax!
DISCLOSURE/DISCLAIMER
If you are booking your property online and have any doubts or questions about a particular property, for example: the location, view, layout, amenities etc., just give us a call at 207-244-3891 or email us. We should be able answer or clarify your concerns.
Our intention is to have "only" satisfied customers. We have tried to provide fair descriptions of the rental properties. On rare occasions, when a renter arrives they are disappointed with the rental unit. Once a lease is signed, there will be no refunds, however, we will do our best to sublet it with owners permission.
If you have any doubts, you should make an effort to view the property in person prior to signing the lease.
More Information
We are continually putting new listings online. If you can't seem to find what you need, please either fill out the Rental Inquiry Form, email us or give us a call at (207) 244-3891 and we'll be glad to help.
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Payment Policy
Rental payments must be in US funds and can be in the form of a personal check, cashier's or certified check,traveler's check or cash. Visa, Master Card, and Discover are now accepted. If paying by credit card there will be a 3.5% administrative fee applied to the payment.