Bailey Island Treehouses, Townhouses & more


1 - 38 of 173

View larger map

Areas near Bailey Island

Great rentals within 20 miles that match your search

1 / 28

East End, Portland, - top neighborhood, near ocean and town

  • 3
  • 8
  • 3 nights min

$270

Details

1 / 22

Townhouse in the Heart of Portland's West End

  • 3
  • 6
  • 3 nights min

$361

Details

1 / 105

Spectacular Views! Vintage waterfront Cottage!!

  • 5
  • 12
  • 3 nights min

$996

Details

1 / 41

Elegant and inviting plantation-style home with two levels of wrap-around decks

  • 4
  • 7
  • 2 nights min

$136

Details

1 / 62

Cozy Cottage

  • 1
  • 2
  • 7 nights min

$108

Details

1 / 4

Oceanfront Cottage on Middle Bay

  • 3
  • 5
  • 7 nights min

$286

Details

1 / 22

Willard Beach - Simone By The Sea - New Home

  • 3
  • 4
  • 3 nights min

$401

Details

1 / 33

Ocean views from every bedroom

  • 5
  • 9
  • Min stay varies

$196

Details

1 / 14

Ocean and Harbor steps from your Cottage

  • 1
  • 4
  • Min stay varies

$90

Details

1 / 13

3 BR 1.5 BA COTTAGE WITH WATER VIEWS OF CASCO BAY

  • 3
  • 5
  • 7 nights min

$191

Details

1 / 19

Stunning Views from this Spacious Oceanfront Home

  • 4
  • 8
  • Min stay varies

$275

Details

1 / 15

The Gatehouse – A

  • 1
  • 2
  • Min stay varies

$161

Details

1 / 8

2 Bedroom Apartment at Moody Beach

  • 2
  • 5
  • 7 nights min

$171

Details

1 / 27

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

  • 2
  • 4
  • 3 nights min

$150

Details

1 / 22

Georgetown (Back River) Vacation Home

  • 5
  • 10
  • Min stay varies

$214

Details

1 / 28

Sunrise Cottage

  • 4
  • 8
  • Min stay varies

$518

Details

1 / 12

Hillcrest Cottage

  • 3
  • 6
  • Min stay varies

$341

Details

1 / 10

Nana's Beach Cottage

  • 3
  • 7
  • 4 nights min

$177

Details

1 / 9

Mackerel Sky Suite

  • 1
  • 2
  • Min stay varies

$110

Details

1 / 12

Oceanfront Shingle Style

  • 6
  • 14
  • 7 nights min

$1001

Details

1 / 13

Willard Beach Get Away - Dog Friendly

  • Studio
  • 3
  • 3 nights min

$196

Details

1 / 27

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

  • 3
  • 6
  • Min stay varies

$160

Details

1 / 24

Oceanfront 4BR w/ Deck, Hot Tub, Bay Views & Studio – Near Bath

  • 4
  • 10
  • Min stay varies

$532

Details

1 / 24

3BR Waterfront Home w/ Backyard Kayak Launch – 5 Mins to Botanical Gardens

  • 3
  • 6
  • 2 nights min

$248

Details

1 / 24

NEW! ‘Heron Cottage’ 1BR South Freeport Cottage

  • 1
  • 4
  • Min stay varies

$231

Details

1 / 24

3BR in Downtown Boothbay Harbor, On the Shore of Mill Cove

  • 3
  • 6
  • Min stay varies

$206

Details

1 / 31

Quaint, family-friendly log cabin only short walk to beach

  • 3
  • 7
  • Min stay varies

$190

Details

1 / 18

13H – Townhome

  • 3
  • 8
  • Min stay varies

$241

Details

1 / 24

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

  • 1
  • 2
  • Min stay varies

$213

Details

1 / 24

Historic Cape Cod with Harbor View, Featured in Coastal Living Magazine!

  • 3
  • 6
  • Min stay varies

$205

Details

1 / 14

3 bed House, Great energy, 4 miles to the Beach!

  • 3
  • 6
  • 4 nights min

$300

Details

1 / 25

Spectacular views of the open ocean and harbor.

  • 3
  • 10
  • Min stay varies

$196

Details

1 / 5

3 bedroom home near beaches

  • 3
  • 8
  • 4 nights min

$275

Details

1 / 30

Spacious, dog-friendly condo w/ deck - walk to the beach, lighthouses & more!

  • 3
  • 7
  • Min stay varies

$140

Details

1 / 12

Adorable 2 Bdr Cottage Apartment _ Casino Beach

  • 2
  • 6
  • 2 nights min

$140

Details

1 / 17

Colorful wonderful Penthouse Apartment

  • 2
  • 4
  • 4 nights min

$95

Details

1 / 28

Open Ocean Estate

  • 3
  • 10
  • 7 nights min

$526

Details

1 / 33

Historic Captain York House: 7 Bed, 6.5 Bath

  • 7
  • 14
  • Min stay varies

$401

Details

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more