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South Freeport Holiday Rentals

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50 rentals in South Freeport.
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New listing! Waterfront home w/ a furnished deck, ocean views, & a full kitchen, holiday rental in South Freeport

New listing! Waterfront home w/ a furnished deck, ocean views, & a full kitchen

2 bedrooms
3 bathrooms
Sleeps 6
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Peaceful Waterfront Apt w/Deck, 22 Mi to Portland!, holiday rental in South Freeport

Peaceful Waterfront Apt w/Deck, 22 Mi to Portland!

1 bedroom
1 bathroom
Sleeps 3
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Spacious Freeport Hideaway w/ 2 Decks & Water View, holiday rental in South Freeport

Spacious Freeport Hideaway w/ 2 Decks & Water View

3 bedrooms
2 bathrooms
Sleeps 6
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NEW! Serene Freeport Cottage on Harraseeket River!, holiday rental in South Freeport

NEW! Serene Freeport Cottage on Harraseeket River!

1 bedroom
2 bathrooms
Sleeps 5
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Maine Oceanfront Home, holiday rental in South Freeport

Maine Oceanfront Home

4 bedrooms
2 bathrooms
Sleeps 11
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Brunswick home near Bowdoin College, holiday rental in South Freeport

Brunswick home near Bowdoin College

2 bedrooms
1 bathroom
Sleeps 5
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Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay, holiday rental in South Freeport

Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay

5 bedrooms
3 bathrooms
Sleeps 10
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PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room, holiday rental in South Freeport

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

5 bedrooms
4 bathrooms
Sleeps 12
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Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views!, holiday rental in South Freeport

Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views!

2 bedrooms
1 bathroom
Sleeps 4
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Oceanside Cottage On A Beautiful Sandy Beach - Enjoy Your Maine Vacation!, holiday rental in South Freeport

Oceanside Cottage On A Beautiful Sandy Beach - Enjoy Your Maine Vacation!

2 bedrooms
1 bathroom
Sleeps 5
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Ocean View Cottage Falmouth Foreside, holiday rental in South Freeport

Ocean View Cottage Falmouth Foreside

2 bedrooms
1 bathroom
Sleeps 5
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Quaint Guest Cottage Overlooking Potts Harbor, holiday rental in South Freeport

Quaint Guest Cottage Overlooking Potts Harbor

1 bedroom
2 bathrooms
Sleeps 3
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Quaint antique island home, holiday rental in South Freeport

Quaint antique island home

3 bedrooms
2 bathrooms
Sleeps 5
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New Well Built Elegant Home on the Water 2 miles to Freeport, 9  to Portland!, holiday rental in South Freeport

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

6 bedrooms
3 bathrooms
Sleeps 12
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THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room, holiday rental in South Freeport

THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room

2 bedrooms
2 bathrooms
Sleeps 4
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Brand new, year-round oceanfront home at the tip of Potts Pt. Private beach., holiday rental in South Freeport

Brand new, year-round oceanfront home at the tip of Potts Pt. Private beach.

3 bedrooms
2 bathrooms
Sleeps 6
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Spacious Water Front Vacation Home with Stunning Views, 5 Bed, 3.5 Bath, holiday rental in South Freeport

Spacious Water Front Vacation Home with Stunning Views, 5 Bed, 3.5 Bath

5 bedrooms
4 bathrooms
Sleeps 12
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Ocean Breezes 2br Freeport, Maine Apartment, holiday rental in South Freeport

Ocean Breezes 2br Freeport, Maine Apartment

2 bedrooms
1 bathroom
Sleeps 4
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Charming Freshly Updated 1BR/1BA Villa with great location close to town & beach, holiday rental in South Freeport

Charming Freshly Updated 1BR/1BA Villa with great location close to town & beach

1 bedroom
1 bathroom
Sleeps 4
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Falmouth Waterfront Carriage House Apt, holiday rental in South Freeport

Falmouth Waterfront Carriage House Apt

1 bedroom
1 bathroom
Sleeps 4
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Family & Pet Friendly Log House On Casco Bay, holiday rental in South Freeport

Family & Pet Friendly Log House On Casco Bay

3 bedrooms
2 bathrooms
Sleeps 6
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Charming Waterfront Cabin in the Woods, holiday rental in South Freeport

Charming Waterfront Cabin in the Woods

2 bedrooms
1 bathroom
Sleeps 5
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Adorable cottage with million dollar view and short walk to stunning beach., holiday rental in South Freeport

Adorable cottage with million dollar view and short walk to stunning beach.

2 bedrooms
1 bathroom
Sleeps 4
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Beautifully decorated executive home steps from a private beach, holiday rental in South Freeport

Beautifully decorated executive home steps from a private beach

3 bedrooms
3 bathrooms
Sleeps 5
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Spectacular Views, Peaceful & Private, holiday rental in South Freeport

Spectacular Views, Peaceful & Private

1 bedroom
1 bathroom
Sleeps 4
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Spectacular Oceanfront House on Maine Coast, holiday rental in South Freeport

Spectacular Oceanfront House on Maine Coast

6 bedrooms
2 bathrooms
Sleeps 10
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Stover's Cove Beach Coastal Retreat, holiday rental in South Freeport

Stover's Cove Beach Coastal Retreat

6 bedrooms
3 bathrooms
Sleeps 14
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HARPSWELL MAINE - The Cottage * AshPoint, holiday rental in South Freeport

HARPSWELL MAINE - The Cottage * AshPoint

2 bedrooms
2 bathrooms
Sleeps 5
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A cottage with a view and so much more!, holiday rental in South Freeport

A cottage with a view and so much more!

4 bedrooms
2 bathrooms
Sleeps 11
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Guest quarters three miles from Freeport, holiday rental in South Freeport

Guest quarters three miles from Freeport

1 bedroom
1 bathroom
Sleeps 2
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Updated waterfront cottage w/private deck, gas grill & dock access, holiday rental in South Freeport

Updated waterfront cottage w/private deck, gas grill & dock access

2 bedrooms
1 bathroom
Sleeps 6
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Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!, holiday rental in South Freeport

Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!

3 bedrooms
2 bathrooms
Sleeps 6
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Island Escape - Spacious 4 BR House with Car included!, holiday rental in South Freeport

Island Escape - Spacious 4 BR House with Car included!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ocean Front Cottage, Harpswell, ME, holiday rental in South Freeport

Ocean Front Cottage, Harpswell, ME

3 bedrooms
1 bathroom
Sleeps 6
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A charming, seaside cottage ~ Falmouth Foreside, holiday rental in South Freeport

A charming, seaside cottage ~ Falmouth Foreside

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront cottage with stunning sunrises over the Cribstone Bridge, holiday rental in South Freeport

Oceanfront cottage with stunning sunrises over the Cribstone Bridge

4 bedrooms
2 bathrooms
Sleeps 6
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Charming Oceanfront Cottage with Spectacular Sunset Views, holiday rental in South Freeport

Charming Oceanfront Cottage with Spectacular Sunset Views

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning views and comfort complete your ultimate Maine island vacation getaway., holiday rental in South Freeport

Stunning views and comfort complete your ultimate Maine island vacation getaway.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Mackerel Cove, Bailey Island. Brand New Fully Equipped Luxury Home. Sleeps 8, holiday rental in South Freeport

Mackerel Cove, Bailey Island. Brand New Fully Equipped Luxury Home. Sleeps 8

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sea Rose Cottage - Cozy and Comfortable with Ocean Views on Orr's Island, holiday rental in South Freeport

Sea Rose Cottage - Cozy and Comfortable with Ocean Views on Orr's Island

3 bedrooms
2 bathrooms
Sleeps 4
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Oceanfront destination property for relaxing and working, for guests of all ages, holiday rental in South Freeport

Oceanfront destination property for relaxing and working, for guests of all ages

7 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Classic Maine Cottage with astonishing easterly views located walking distance t, holiday rental in South Freeport

Classic Maine Cottage with astonishing easterly views located walking distance t

3 bedrooms
1 bathroom
Sleeps 5
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Historic cottage with views of Mackerel Cove and right of way to Little Harbor!, holiday rental in South Freeport

Historic cottage with views of Mackerel Cove and right of way to Little Harbor!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming cottage on Basin Cove just a short drive to the Dolphin Marina, holiday rental in South Freeport

Charming cottage on Basin Cove just a short drive to the Dolphin Marina

3 bedrooms
1 bathroom
Sleeps 5
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Classic Maine Beach Cottage, private beach access, holiday rental in South Freeport

Classic Maine Beach Cottage, private beach access

3 bedrooms
1 bathroom
Sleeps 5
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Classic Oceanfront Cottage on Orr's Island, holiday rental in South Freeport

Classic Oceanfront Cottage on Orr's Island

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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'Heron Cottage' on Casco Bay w/Deck & Dock Access!, holiday rental in South Freeport

'Heron Cottage' on Casco Bay w/Deck & Dock Access!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in South Freeport

Luxury Coastal Home w2 Living Rooms, Pool, Rooftop

6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in South Freeport

Luxury Coastal Home w2 Living Rooms, Pool, Rooftop

6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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NEW! Charming Home w/ Deck - Steps to Casco Bay!, holiday rental in South Freeport

NEW! Charming Home w/ Deck - Steps to Casco Bay!

1 bedroom
3 bathrooms
Sleeps 7
Match: Sleeps
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