Southport Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

321 Houses

31

6BR Waterfront Estate on Pratt’s Island w/ Bunk House & Loft - Near Dining

Mid Coast Maine / Southport

Southport house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$570

Price per night from

$570

17

THE LEDGE ON SOUTHPORT ISLAND | TIDAL OCEAN FRONT | CHARMING SUMMER COTTAGE |

Southport / Newagen

Newagen house

3 4 4 nights min

  • 3 bedrooms
  • sleeps 4
  • 4 nights min
  • Ask about children
  • Air conditioning

Price per night from

$464

Price per night from

$464

30

Family Friendly Shoreside 5BR w/ Island View, Near Boothbay Harbor & Downtown

Mid Coast Maine / Southport

Southport house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$675

Price per night from

$675

9

OCEAN WAY ON SOUTHPORT ISLAND | QUIET WOODLAND RETREAT NEAR BEACH

Mid Coast Maine / Southport

Southport house

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$164

Price per night from

$164

17

SPRUCEROCK COTTAGE | SOUTHPORT ISLAND MAINE | OCEANFRONT | FAMILY VACATION | PET

Southport / Newagen

Newagen house

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 6 mi
  • Ask about children
  • Air conditioning

Price per night from

$315

Price per night from

$315

25

2BR Southport Island Cottage w/ Deck & New Luxe Kitchen, Near Boothbay Harbor

Mid Coast Maine / Southport

Southport cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$164

Price per night from

$164

Great rentals within 20 miles that match your search

Distance approx 16.06 km from Southport

(3) Excellent 

19

Mazu, the Bed&Boat, the most waterfront cottage

Mid Coast Maine / Damariscotta

Damariscotta yacht

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary

Price per night from

$225

Price per night from

$225

Distance approx 15.29 km from Southport

(12) Excellent 

16

Peaceful Lakeside Cabin on Shores of Biscay

Mid Coast Maine / Bremen

Bremen log cabin

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Child Friendly

Price per night from

$125

Price per night from

$125

Distance approx 13.12 km from Southport

(1) Excellent 

24

"Top of The World Vista" Edgecomb Cottage!

Mid Coast Maine / Edgecomb

Edgecomb studio

Studio 4 min stay varies

  • Studio
  • sleeps 4
  • min stay varies
  • Suitable for children age 5+

Price per night from

$200

Responds fast!
avg. 46 minutes

Price per night from

$200

Distance approx 19.12 km from Southport

20

The Barn

Mid Coast Maine / Alna

Alna house

3 12 7 nights min

  • 3 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 15 mi
  • Child Friendly
  • Air conditioning

Price per night from

$300

Responds fast!
avg. 3 hours 13 minutes

Price per night from

$300

Distance approx 8.09 km from Southport

(4) Excellent 

8

Tidewater Popham Beach House

Mid Coast Maine / Phippsburg

Phippsburg house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.01 mi
  • Child Friendly

Price per night from

$225

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$225

Distance approx 19.06 km from Southport

(5) Excellent 

20

Ocean Front Cottage, Harpswell, ME

Mid Coast Maine / Harpswell

Harpswell cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$221

Price per night from

$221

Distance approx 10.2 km from Southport

(1) Excellent 

8

Waterfront Cottage, Stroll Away from Historic Bath

Mid Coast Maine / Bath

Bath cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 25 mi
  • Child Friendly

Price per night from

$239

Responds fast!
avg. 55 minutes

Price per night from

$239

Distance approx 12.71 km from Southport

8

Vintage Cottage with Spectacular Water Views!

Mid Coast Maine / Wiscasset

Wiscasset house

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$995

Price per night from

$995

Distance approx 12.93 km from Southport

(6) Excellent 

Certificate of Excellence

20

Camp Forever

Mid Coast Maine / Harpswell

Harpswell studio

Studio 3 2 nights min

  • Studio
  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Certificate of Excellence

Price per night from

$175

Responds fast!
avg. 8 minutes

Price per night from

$175

Distance approx 12.36 km from Southport

16

Romantic Harbour-side Studio 52w

Mid Coast Maine / Edgecomb

Edgecomb apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child Friendly

Price per night from

$150

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$150

Distance approx 18.56 km from Southport

(1) Excellent 

24

Charming oceanfront cottage

York / Cape Neddick

Cape Neddick cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$264

Responds fast!
avg. 1 hour 41 minutes

Price per night from

$264

Distance approx 4.84 km from Southport

105

Spectacular Views! Vintage waterfront Cottage!!

Mid Coast Maine / Wiscasset

Wiscasset house

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$995

Responds fast!
avg. 53 minutes

Price per night from

$995

Distance approx 12.9 km from Southport

(1) Very Good 

146

Lofty Cottage

Mid Coast Maine / Harpswell

Harpswell cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$246

Price per night from

$246

Distance approx 3.01 km from Southport

9

Ocean Point, Maine Cottage Weekly Rental

Boothbay / East Boothbay

East Boothbay cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Private garden

Price per night from

$244

Price per night from

$244

Distance approx 5.95 km from Southport

(2) Very Good 

14

Maine Cottage, Mid-Coast Maine

Mid Coast Maine / South Bristol

South Bristol cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 mi
  • Child Friendly

Price per night from

$129

Price per night from

$129

Distance approx 16.85 km from Southport

(3) Excellent 

12

Executive furnished Penthouse in Brunswick, Maine.

Mid Coast Maine / Brunswick

Brunswick apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Nearest beach 30 mi
  • Air conditioning
  • Pet Friendly
“Great interior, great location, great landlord!” The penthouse is tastefully furnished with a spacious yet cozy layout, with the bed area out of sight of the living room and kitchen. The bathroom is small but very nice. Comes with a large television a
…see more

Price per night from

$80

Responds fast!
avg. 2 hours 3 minutes

Price per night from

$80

Distance approx 13.58 km from Southport

156

Camp Card Cove

Mid Coast Maine / Harpswell

Harpswell house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$464

Price per night from

$464

Distance approx 8.09 km from Southport

(6) Excellent 

8

Laughton House & Cottages - Cabin - Ebb Tide

Mid Coast Maine / New Harbor

New Harbor cottage

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.04 mi
  • Child Friendly

Price per night from

$110

Responds fast!
avg. 19 minutes

Price per night from

$110

Distance approx 2.67 km from Southport

(45) Excellent 

27

Boothbay Harbor Pet-Friendly High-Tech House Lake Access Near Ocean

Mid Coast Maine / Boothbay Harbor

Boothbay Harbor cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly
“What a great place to stay!” We stayed in the Lake View Cottage. The description doesn't do it justice and we loved it up there. Our son was especially excited that the beach was right across the way and that there was a little boy in Ocean View Cotta
…see more

Price per night from

$225

Price per night from

$225

Distance approx 19.33 km from Southport

8

2 Bedroom Apartment at Moody Beach

Maine / Wells

Wells apartment

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly

Price per night from

$171

Responds fast!
avg. 3 hours 10 minutes

Price per night from

$171

Distance approx 12.71 km from Southport

27

Cliffside Cottage on Westport Island, Maine

Mid Coast Maine / Wiscasset

Wiscasset converted chapel

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$475

Price per night from

$475

Distance approx 4.68 km from Southport

26

Lake Cottage on Knickerbocker Lake Boothbay ME.

Mid Coast Maine / Boothbay

Boothbay house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$243

Price per night from

$243

Distance approx 18.68 km from Southport

(3) Excellent 

27

Private Island - Great for Reunions - Sleeps 24

Mid Coast Maine / Port Clyde

Port Clyde house

11 24 7 nights min

  • 11 bedrooms
  • sleeps 24
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$2,142

Price per night from

$2,142

Distance approx 8.09 km from Southport

38

Immaculate And Very Private Boothbay Region Waterfront Home

Mid Coast Maine / Edgecomb

Edgecomb house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 25 mi
  • Child Friendly

Price per night from

$250

Price per night from

$250

Distance approx 17.81 km from Southport

15

Brand New Modern Loft Home

Mid Coast Maine / Topsham

Topsham house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly

Price per night from

$120

Price per night from

$120

Distance approx 8.03 km from Southport

29

Dog-Friendly Ocean Beach Rental, Level 1

Mid Coast Maine / Phippsburg

Phippsburg cottage

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$360

Price per night from

$360

Distance approx 17.67 km from Southport

161

Schooner Landing

Mid Coast Maine / Harpswell

Harpswell cottage

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$356

Price per night from

$356

Distance approx 12.04 km from Southport

16

Waterfront Home on Scenic Cove

Mid Coast Maine / Harpswell

Harpswell house

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$160

Price per night from

$160

Distance approx 10.6 km from Southport

(9) Very Good 

17

Minutes from Popham Beach - Cozy Maine Coast Cottage

Mid Coast Maine / Phippsburg

Phippsburg cottage

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$190

Price per night from

$190

Distance approx 9.21 km from Southport

(6) Excellent 

21

Victorian Cottage on Westport Island

Mid Coast Maine / Wiscasset

Wiscasset cottage

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$200

Price per night from

$200

Distance approx 12.99 km from Southport

(8) Excellent 

16

Cozy 2-bdrm w/ lg deck overlooking Round Pond cove

Mid Coast Maine / Round Pond

Round Pond house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$75

Price per night from

$75

Distance approx 12.56 km from Southport

(10) Excellent 

12

Charming ocean front cottage in Harpswell

Mid Coast Maine / Harpswell

Harpswell cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 22 mi
  • Child Friendly

Price per night from

$132

Responds fast!
avg. 3 hours 10 minutes

Price per night from

$132