Southport Holiday Rentals

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Holiday Rentals 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

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (148)
"What a perfect place to unwind and watch the sunrise. "
1 room luxury ocean front studio cottage

Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

9.4 out of 10, Exceptional, (51)
"There were four of us so we each had a bedroom. We have been friends since 1955!!! It was a wonderful getaway! "
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

9.6 out of 10, Exceptional, (65)
"Our stay was amazing and everything was just as we expected, and more! Highly recommend this log cabin in the woods in quiet Maine"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

9.4 out of 10, Exceptional, (42)
"Beautiful location "
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (96)
"Beautiful cottage with an amazing view of the bay. Great porch where we spent most of our time. Very convenient to Damariscotta. Great setting for two couples. "
A Charming Waterfront Cottage with Touches of Elegance

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

8.4 out of 10, Very good, (41)
"GORGEOUS house and view! Very spacious and accommodating. Things you should know before booking is that it is about an hour away from anything and everything. House could use some more TV's if you're going with children, pinball machines did not work and neither did "workout equipment" which was an elliptical and treadmill. One of the showers did not work and some of the fans that were provided did not either. I think its a tad over priced for its distance to do things but the views from...
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (80)
"If you like eclectic you'll love this place. Quite rustic. "
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

9.4 out of 10, Exceptional, (30)
"This house was amazing. It was way better than we expected after looking through the pictures online. The outdoor space and the house itself are beautiful and the pictures do it zero justice. We were worried at first about the lack of AC, but the house cooled right down once we opened the windows let the air in. I highly recommend this place if you’re looking to visit Boothbay. It was so close to the main area, but you couldn’t even tell- it felt like you were immersed in nature."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (35)
"Our party of 8 enjoyed our stay. The house is well equipped and stocked to get you started. Conveniently located to town and the Botanical Gardens. Plenty of outside space for kids to run around and play. It has a beautiful view of the cove but is very rocky. This didn't stop us from hunting hermit crabs and catching fish. The house is old but that gives it the Maine charm. "
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Popham Beach Direct Oceanfront Cottage Steps to the sand

9.8 out of 10, Exceptional, (58)
"Well taken care of and maintained. Comfortable."
Popham Beach Direct Oceanfront Cottage Steps to the sand

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (53)
"Property was great. But we had no water for one of our three days of our stay. We had to call to get someone out to fix it, and they didn’t know how. It set the tone for our stay."
Unique oceanfront home with a deck, tons of natural light, & amazing views

Cozy Cottage with spectacular salt water view / 3 Kayaks available/

9.8 out of 10, Exceptional, (38)
"I had an excellent visit. The kitchen was well stocked with utensils and small appliances. Everything was super clean; magazines and books were available (as well as good WiFi). I never turned the tv on as the view was spectacular. I wasn’t able to have an outdoor fire due to weather but everything was great. I hope to return. I look forward to doing more exploring as the area is beautiful. Also, very responsive with owners live next door. Thanks for offering up this quant little cabin for...
Cozy Cottage with spectacular salt water view / 3 Kayaks available/

Riverfront condo w/ deck overlooking the water - steps to dining & shopping

9.0 out of 10, Wonderful, (41)
"Overall it was great for the money!"
Riverfront condo w/ deck overlooking the water - steps to dining & shopping

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

9.6 out of 10, Exceptional, (65)
"This is my 3rd time staying at this lovely place. Everything is beautifully clean and well maintained. Check in is seamless. I have never seen a kitchen so well equipped. you can literally cook anything here! The location is within walking or a few minutes driving distance to all the attractions on the peninsula. I am so looking forward to returning! "
Slow Down & Go Back in Time-Relax Completely in Our Maine Home

Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer

8.8 out of 10, Excellent, (13)
"Nice views of tidal river "
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.8 out of 10, Exceptional, (24)
"It was just as advertised. Nice ,clean and very comfortable! I would love to stay here again !"
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town
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 types of properties in Southport you may be interested in

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

The Brunswick Hotel

3.0 star property
9.2 out of 10, Wonderful, (714)
"Last minute late night booking and was pleasantly surprised with this quiet and charming hotel. Staff upon check-in were lovely and accommodating. Room was spacious and had an amazingly comfortable bed with very nice sheets. Pillows are amazing. Complimentary toiletries and bottled water added to a great relaxing evening after a long day on the road. Breakfast was a little hum-drum run of the mill stuff, but property and good sleep made up for it! Would definitely recommend to others, and would...
The price is AU$215
includes taxes & fees
1 Dec - 2 Dec
The Brunswick Hotel

Tugboat Inn

3.0 star property
9.0 out of 10, Wonderful, (1091)
"It’s the perfect location to explore Boothbay Harbor! Loved the beautiful deck 😍"
The price is AU$236
includes taxes & fees
2 Dec - 3 Dec
Tugboat Inn
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Southport?

Yes, there are holiday rentals close to the most popular sights in Southport, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Southport is known for its waterfront and seaside. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Southport has to offer?

Stunning oceanfront cottage w/ private deck and Atlantic views: This highly rated holiday home rental in Southport is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Southport?

With 24 Expedia holiday rentals, you're guaranteed to find just the right place for your Southport stay.

What’s there to see and do in Southport?

Cultural attractions include Hendricks Hill Museum, whereas Hendricks Head Beach is a spot to enjoy nature. While here, Hendricks Head Light and Southport Memorial Library are other places worth a visit.

What’s a holiday rental in Southport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Southport. Holiday rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.