Vacation rentals in Southport Island

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Top-rated vacation rentals in Southport Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 342 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Jan 19 – 26

$134 per night
Guest favorite

Apartment in Edgecomb

4.91 out of 5 average rating, 296 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

Oct 21 – 28

$87 per night
Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 428 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

Nov 5 – 12

$120 per night

Popular amenities for Southport Island vacation rentals

Other great vacation rentals in Southport Island

Guest favorite

Guest suite in Georgetown

4.97 out of 5 average rating, 320 reviews

Luxury suite, fireplace, jacuzzi

Dec 29 – Jan 5

$190 per night
Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 102 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Feb 12 – 19

$85 per night
Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Oct 23 – 30

$140 per night
Guest favorite

Tiny home in Dresden

4.96 out of 5 average rating, 160 reviews

Maplenook Tiny Cabin - A Cozy Woodland Oasis

Jul 15 – 22

$99 per night
Guest favorite

Apartment in Boothbay

4.94 out of 5 average rating, 177 reviews

Farnham Point Retreat

Nov 12 – 19

$152 per night
Guest favorite

Tiny home in Georgetown

5.0 out of 5 average rating, 54 reviews

Studio Cabin on Pond+Near Beach+Porch+AC+FirePit

Nov 7 – 14

$133 per night
Guest favorite

Apartment in Boothbay Harbor

5.0 out of 5 average rating, 60 reviews

Harbor for Two

Nov 10 – 17

$120 per night
Guest favorite

Guest suite in Boothbay

4.95 out of 5 average rating, 86 reviews

Linekin Guest Suite

Apr 22 – 29

$68 per night
Guest favorite

Cottage in Boothbay

5.0 out of 5 average rating, 100 reviews

Cottage in the woods on Ocean Point

May 6 – 13

$125 per night
Guest favorite

Cottage in Southport

5.0 out of 5 average rating, 37 reviews

THE COVE: New England Charm / Sprinkle of Nautical

Feb 24 – Mar 3

$500 per night
Guest favorite

Apartment in Boothbay

5.0 out of 5 average rating, 25 reviews

The Chickadee's Nest

Oct 23 – 30

$125 per night
Guest favorite

Cottage in Georgetown

4.98 out of 5 average rating, 98 reviews

Cottage on Todd Bay

Oct 21 – 28

$142 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Lincoln County
  5. Southport
  6. Southport Island