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Bailey Island Rentals

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Price range

Per night

$10 - $500

Bailey Island Rentals

203 Houses

Historic Captain York House: 7 Bed, 6.5 Bath

Bailey Island house

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$498

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Open Ocean Estate

Bailey Island house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$528

1 / 28

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

Bailey Island cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$125

1 / 13

Quaint waterfront cottage with large deck and gorgeous views!

Bailey Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$110

1 / 20

Deepwater front home with beautiful sunsets

Bailey Island apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

1 / 21

A spectacular private location with Sunrise and Sunset views.

Bailey Island cottage

4 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$257

1 / 30

Lovely Cape situated at the waters edge with picturesque sunset views to Mt Wash

Bailey Island house

4 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$450

1 / 30

Quintessential Maine Cottage Overlooking the World Famous Cribstone Bridge! Fres

Bailey Island cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$135

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Whitesails Cottage - Lovely deck to watch the boats, and incredible sunsets!

Bailey Island cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$110

1 / 15

Panoramic ocean views from sunrise to sunset!

Bailey Island house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$200

1 / 20

Recently renovated home on a quiet road, enjoy westerly water views over Harpswe

Bailey Island house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$150

1 / 18

Spectacular sunset views from the wrap-around deck of this comfortable ranch.

Bailey Island cottage

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$285

1 / 6

Romantic Shorefront Cottage on Harpswell Sound

Bailey Island cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$150

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Two bedroom cozy cottage with beautiful views of Mackerel Cove and the Bay!

Bailey Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$125

1 / 10

Steamboat Landing - Perched on the shore of picturesque Mackerel Cove.

Bailey Island cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

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McCollum Cottage -Classic Maine Cottage located on water`s edge on Bailey Island

Bailey Island cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$115

1 / 19

A quaint, charming and comfortable Maine cottage.

Bailey Island cottage

5 bedrooms / 1 bathroom / sleeps 6

Price per night from

$214

1 / 21

Enjoy spectacular Easterly Ocean views!

Bailey Island cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$222

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Great rentals within 20 miles that match your search

Spectacular Ocean Views & Private Beach, Minutes from Popham & Sebasco Resort

Phippsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$199

1 / 29

3 bedroom home near beaches

Cape Elizabeth house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$277

1 / 5

Quiet Lake Serenity Just 10 Miles from Portland

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$273

1 / 15

2BR / 1B - Willard Beach -- South Portland

South Portland apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 54 minutes

Price per night from

$151

1 / 31

Willard Beach Modern Apartment

South Portland apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$126

1 / 9

Spectacular Views! Vintage waterfront Cottage!!

Wiscasset house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 53 minutes

Price per night from

$1,001

1 / 105

NEW! ‘Osprey Cottage’ 2BR South Freeport Cottage

South Freeport cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 19 minutes

Price per night from

$252

1 / 24

2 Bedroom Apartment at Moody Beach

Wells apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 10 minutes

Price per night from

$172

1 / 8

Classic Maine Beach Cottage, private beach access

Falmouth cottage

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$202

1 / 11

Spectacular Views! 800 deep water feet, 3.5 acres!

Wiscasset cottage

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$1,001

1 / 69

NEW LISTING: Stunningly Renovated Beach House with OCEAN VIEWS-150 yds to beach

South Portland house

4 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 2 hours 36 minutes

Price per night from

$599

1 / 63

Pet Friendly West Bath Home w/Dock, Beach & Canoe!

Harpswell cottage

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 10 minutes

Price per night from

$110

1 / 29

WESTPORT ISLAND-Luxury Waterfront Cabin-Amazing Views-Quiet & Private Road

Wiscasset cottage

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 12 minutes

Price per night from

$714

1 / 23

NEW! Waterfront Apt w/Deck - 22 Min. to Portland!

Freeport apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 22 minutes

Price per night from

$106

1 / 28

Comfort | Location | Charm

Portland house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$178

1 / 6

Dog-Friendly Ocean Beach Rental, Level 1

Phippsburg cottage

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$360

1 / 29

Waterfront Home on Scenic Cove

Harpswell house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$161

1 / 16

Nice Cozy 2 Bedroom Beach Cottage at Higgins Beach

Scarborough house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$273

1 / 8

Price per night from

$503

1 / 26

Classic, cozy family cottage with modern amenities and ocean view from porch

Peaks Island cottage

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 53 minutes

Price per night from

$352

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Viewing 38 of 203
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