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Compare 384 Vacation Homes in Southport with updated reviews, rates, and availability.

Admiral's Quarters - Room 12
8.8 out of 10, Excellent, (5)
"We had a wonderful time at Admiral’s Quarters and wish we’d had one more night to spend in Boothbay Harbor. Our room was cozy and the two levels made it perfect for our family of four. The location was fantastic and John always had great recommendations for things to do or places to eat. "
The price is AED 1,350
AED 1,734 total
includes taxes & fees
25 Nov - 26 Nov
Admiral's Quarters - Room 12
Oceanfront Cabin-Castle in Maine Woods
9.8 out of 10, Exceptional, (8)
"We had a great time during our stay. Very fun and unique placeb to stay. We had a little pine squirrel make his way into the house with us somehow, but the host was very understanding and it didnt take away from our stay at all. Thanks, Micah, we hope to be back. "
Oceanfront Cabin-Castle in Maine Woods
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
10.0 out of 10, Exceptional, (66)
"We have stayed at several VRBO and this one was the best. Great location and great house."
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Full sized home
9.6 out of 10, Exceptional, (22)
"Short visit but fun little cottage off the beaten path. Most comfortable beds ever and very responsive host and caretaker. Would stay here again. Loved the nearby waterfront restaurants."
The price is AED 826
AED 1,361 total
includes taxes & fees
25 Nov - 26 Nov
Full sized home
Quintessential Maine Oceanfront home
10.0 out of 10, Exceptional, (70)
"Had a wonderful time at the home. The views are just beautiful!"
Quintessential Maine Oceanfront home
Home In Boothbay - Holiday Getaway
9.4 out of 10, Exceptional, (10)
"Great trip. Home met all our needs. It needs tables by the couch and perhaps another chair in tv room. But it was comfortable and homey. "
Home In Boothbay - Holiday Getaway
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
10.0 out of 10, Exceptional, (4)
"I can’t say enough about the house and our wonderful hosts. They’ve created a wonderful memory for our friends and family that will last a lifetime. The house, the views, boothbay harbor and all that it has to offer. Best vacation ever!! THANK YOU SO MUCH!! Paul"
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
9.6 out of 10, Exceptional, (33)
"The house we stayed in was wonderful. It met all of our expectations. I highly recommend it!"
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
Beautiful house on the Harpswell Peninsula over looking Casco Bay
9.8 out of 10, Exceptional, (59)
"Comfortable, peaceful. Everything we needed for mussels, steamers and lobster Nice to have working dock in front of us for lobsters"
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
9.6 out of 10, Exceptional, (32)
"Great location, very easy to get to harbor, and a great view. Check-in was easy, not having to keep a key on you was also nice. The house was very cozy, perfect for doing puzzles or drinking coffee in the morning. Lots of appliances and home goods to make it easy to cook, iron clothes, hang stuff, etc. Overall we would definitely stay again!"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
9.0 out of 10, Wonderful, (56)
"Beautiful house with lots of charm….. gorgeous views from the deck. I was texted when we arrived to make sure we were happy with the cleanliness of the home and we were . House was supplied with plenty of towels, blankets, toiletries, cushions for outdoor furniture and games. We stayed here with our dogs who loved it as well. We would stay here again"
The price is AED 378
AED 1,166 total
includes taxes & fees
24 Nov - 25 Nov
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Shady Potts Point Cottage Cooled by Ocean Breezes
9.6 out of 10, Exceptional, (77)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
5.6 out of 10, (5)
"The shared driveway was a challenge and the hike from the driveway to the house had was also a challenge. Additionally the window in one of the bathrooms did not work, the dishwasher was not secured and tilted when you put dishes in, one of the commodes ran constantly unless you jiggle. The kitchen garbage can is broken."
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
9.6 out of 10, Exceptional, (35)
"It is a big house with 4 bedrooms and 2 full baths. It was very clean when we arrived It is about a half mile walk into Boothbay Harbor by way of the footbridge. There are many restaurants, and shops. You can go out on boat tours from the middle of the town. Our experience was very good and be enjoyed our stay"
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
Cottage in Edgecomb - Waterfront Holiday Getaway
10.0 out of 10, Exceptional, (25)
"Wonderful home, very clean and well stocked "
Cottage in Edgecomb - Waterfront Holiday Getaway
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
10.0 out of 10, Exceptional, (50)
"This was our first trip to Maine and this home was our first stop (of three) during our stay. It definitely was our favorite! We enjoyed being welcomed by Carol and having the chance to ask questions. Having Reid State Park nearby is like having a beach in your backyard (thanks for the pass). I've stayed in numerous vrbos over the years and, by far, Michael is the most responsive host I've encountered. "
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away
10.0 out of 10, Exceptional, (90)
"Beautiful location, really enjoyed the stay. The stairs are a challenge especially with no landing at the top. Didn't receive any notification about check-in and I got no answer when I called but when I checked the door was unlocked and keys were on the table. Everything was very clean and the kitchen was well equipped. "
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away
Downtown Boothbay Harbor, The Francis Greene House
9.4 out of 10, Exceptional, (39)
"It was our third time staying on this property...the beds are so comfortable we didn't want to leave...the house is located a nice distance from town...a quick 5 minute walk...just far enough away you don't hear any in town noises at night..sunrises in the porch or dining room are beautiful...already planning our next trip there"
Downtown Boothbay Harbor, The Francis Greene House
Luxury Carriage House a short stroll from town!
2.0 star property
10.0 out of 10, Exceptional, (5)
"Amazing location and beautiful little property. Everything was immaculate and welcoming, and we felt so taken care of, down to the small touches like just the coffee we like! Communication was great and timely, too. We'll definitely be back next time we are in Maine!"
The price is AED 1,098
AED 1,806 total
includes taxes & fees
3 Dec - 4 Dec
Luxury Carriage House a short stroll from town!
Blue Lobster! 2-bedroom house with Heat, AC, Deck and Seasonal Dock in Harpswell
2.0 star property
9.6 out of 10, Exceptional, (11)
"Great location! Easy access to the remote islands but also close enough to Brunswick and highway. The house was perfect for my husband and I. The owners have the kitchen well stocked and we were able to cook and eat our own lobsters at home so we can enjoy the magnificent view. Both owners were very helpful with any questions we had"
Blue Lobster! 2-bedroom house with Heat, AC, Deck and Seasonal Dock in Harpswell
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Southport

Stunning oceanfront cottage w/ private deck and Atlantic views
9.2 out of 10, Wonderful, (50)
"They thought of everything, including binoculars. We watched seabirds and lobstermen working and didn't leave the house until late in the day for the Botanical Gardens. They only communicate through Vacasa,email, and text. Good communication, though. Final payment is through Vacasa. "
Stunning oceanfront cottage w/ private deck and Atlantic views
East Boothbay Waterfront One room Condo.Waterview from in side this room
9.8 out of 10, Exceptional, (127)
"perfect love to be back next year"
East Boothbay Waterfront One room Condo.Waterview from in side this room
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
8.2 out of 10, Very Good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.