House holiday rentals in Southport

Great backyard with a pool, hot tub, fire pit and privacy with the woods.

We felt like at home. The house is located in a private property with swimming pool and tennis courts. It’s very clean and very peaceful. Just a clarification about the description : there’s no bathroom in the basement. Then if you come with elderly people or very young kids, it could be annoying. If you like cooking, the kitchen is very well equipped. We´ll keep a very good memory of our stay in Ducktrap Retreat during the colorful foliage season.

I hosted a group of 8 girls here for a bachelorette and we can’t say enough great things about the place. It was clean and exactly how described. There was plenty of parking space for multiple cars. The hot tub was an enjoyable extra amenity. Jey was quick to respond with any concerns or questions. The home was a quick 20 minute drive from downtown Portland.

Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!

Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!

Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!

Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

Kimberly’s “Quiet Oasis” was a perfect home base for our family vacation in Boothbay Harbor. The house is clean, spacious, and well-equipped – we had everything we needed for cooking big meals at the house or for lazy afternoons hanging out on the deck. It was very private and quiet, and we older folks loved having a separate suite on the second floor. We enjoyed visiting Barrett Park nearby, and the house is also convenient to Boothbay Harbor – it’s either a nice one-mile walk to the footbridge or a very quick and easy drive into town. Check-in was easy and Kimberly was quick and clear with answers to all of our questions. Overall a top pick for a vacation house in beautiful Boothbay – groups of up to six will be happy and comfortable there.

Very pretty location and private 😊 This is a lovely and authentic older home and reminded me of my great grandmother’s home with creaky wood floors and homey atmosphere! We were just sorry that we didn’t have enough time to enjoy the beautiful stone patio for morning coffee or evening meals!

Close to fun brewery across street , close to downtown area . Just stayed two nights was nice get away.

Wow. What a beautiful cottage on a beautiful bay in a beautiful state. Wonderful host and super convenient to northern and southern spots of Maine to visit. Everyone is nice and kind in Round Pond.

Simply magical! Cozy and fun space. We enjoyed watching eagles and ospreys fish, seals pop their heads up, and even an adorable family of foxes from the comfort of the living room! Kitchen had all necessities for cooking most meals at home. A nice trail for walking down the road and an awesome beach where the kids threw stones and searched for seaglass each afternoon. We were all sad to leave!

Everything from start to finish was absolutely amazing. The house is beautiful with all the amenities you need. The outside fire pit was nice to sit out and enjoy the nice weather. The communication with Jody was fast and she was very accommodating to our needs. Thank you so much for a wonderful stay

The house was beautiful and in a great location. The owners were extremely responsive and kind! We had a wonderful weekend at this incredible house.

This place has all the comforts of home and then some. Very thoughtful amenities including a smart TV, a turntable with a small eclectic vinyl collection, and indoor and outdoor games. Every room having lightswitches with dimmers and the separate climate control units in each bedroom were great! With beach gear available for a quick drive down to Popham and being able to bring the outdoors indoors by opening up the two retractable doors on the first floor were fantastic! Alina and Brian are very communicative and accommodating. We will certainly be staying here again for our next trip.

Modern Farm House with old bones and modern amenities. Beyond impressed with the amount of supply’s this home provided. Fully equipped on literally everything you would ever need and MORE for a family friendly stay. Home was clean, fully stocked, slept well, plenty of pace for your own privacy and location, location, location. Short car ride or walk to harbor bonus free parking for your vehicles which allows you to leave your car at home and walk to town. The owner Jules was so sweet simple and easy going! We stayed for our son’s college graduation from Colby College 1 hour away allowing our other family guests time to enjoy Boothbay. WIN WIN! Thank you for a wonderful stay!

Mihai is a wonderful host and his place is a gem! The gorgeous location is nothing short of magical and the house is immaculately designed and decorated. The hot tub is an amazing bonus. Everything about our stay went smoothly and even during off season, we found plenty to do. Would absolutely stay again.

Great location on Back River. short drive to wiscasset and groceries. Fun to sit and watch the tides.

We had a great stay at Chris’s house! It has all the modern conveniences but is warm and comfortable, and fits well in the neighborhood. The location right on the cove has great views from the living area and the bedroom. The house is very well appointed with comfortable furniture, a well-stocked kitchen and a great king bed. Heating system worked well and water pressure was good. Filtered water from the refrigerator was a plus. Washer/dryer came in handy, and parking was easy. Boothbay Harbor is quiet in the off-season but it was great to not have crowds and traffic. It’s an easy walk to downtown and some restaurants and shops were open. We had breakfast at Woodsong Market (great coffee too!) and dinners at the Boathouse and Brady’s - both were very good. The house was also a good home base to visit other towns - Southport, Bath, Brunswick, Rockland and Belfast. Thanks again Chris for sharing your terrific home!

The home is a bargain for the price! The place was spotless, and the host Rochelle was proactive with the checking instructions and very kind. Would highly recommend for anyone visiting the beautiful town of Boothbay Harbor

Beautiful home and area! Convenient to everything! Good communication w olive and co. We had a great stay seeing an amazing show of the northern lights from the bedroom deck!!

Our stay at Laurel Shore Cottage was just what we needed. The location was serene - and we spent most afternoons and evenings sitting on the porch soaking in the beautiful landscape and scenery. The cottage itself was uncluttered and comfortable and the host was very responsive.

Beautiful setting. Great host. Quiet. Tranquil. Peaceful. Once we navigated the dirt road we enjoyed the drive to restaurants. Into Bath. Reid State park was amazing. We liked The Osprey. We loved Blue at Grey Havens.