Experience Small-town Maine Living in Bailey Island Rentals

Bailey Island, Maine is a wonderful summer getaway destination for families and couples alike. Here, you’ll find the comfort of home in Bailey Island rentals and plenty of fun in the sun with access to neighboring Orr Island, too.

Stay in Bailey Island Rentals for a Cozy Getaway


Several Bailey Island vacation rentals have been touted for their attention to detail and rustic décor made to make visitors feel welcome. Schedule a short weekend away with your sweetie, and take advantage of the nearly world-famous seafood at one of the local restaurants, too. Choose Bailey Island, ME rentals on the beach for a romantic evening walk, or relax while watching the sunset together.

Day Trips from Bailey Island Vacation Rentals


Since the construction of the Cobwork Bridge, which connects Bailey Island to Orr Island, the choices in things to do here have literally become endless. Since you most likely will drive to stay in Bailey Island rentals, simply hop in the car and explore an additional island that offers Maine’s best food and attractions.

Bailey Island vacation rentals are also located near The Giant Steps, an interesting rock formation that looks much like a flight of stairs on the edge of the island. Bailey Island, ME rentals demand a visit to Mackerel Cove, as this is known as one of the top-photographed locations in Maine.

Access Local Beaches near Bailey Island ME Rentals


Your entire group will love a day at Land’s End, a famous beach located near Bailey Island rentals. This is an ideal location, as Bailey Island vacation rentals are located in an area famous for rocky beaches. Birds and other wildlife reside here, and you’ll find plenty of photo opportunities during mating and migrating seasons. Your choice in Bailey Island, ME rentals offers access to a multitude of activities and natural attractions the entire family can enjoy during your stay.

Still searching for the perfect vacation rental in the Portland and Casco Bay area? Consider staying in rentals in Brunswick, Cape Elizabeth rentals, Freeport vacation rentals, Harpswell lodging, Orr's Island rentals, rental lodging in Phippsburg, Popham Beach rentals, or rentals in Portland.

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Bailey Island: Cottages, Houses & More(42)

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Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
    5 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 10
$500 - $600
per night

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

Book it Now!
3 - 7 night Minimum Stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
  1. Portland and Casco Bay Area >
  2. Bailey Island House
#465503vb
    New as of June 2012 - Ocean Breeze Cottage on Casco Bay with Beach
      2 Bedrooms,
    • 1 Bathroom
      • , Sleeps 6
    $200 - $330
    per night

    New as of June 2012 - Ocean Breeze Cottage on Casco Bay with Beach

    2 night Minimum Stay
    • 2 BR,
    • 1 BA,
    • Sleeps 6
    1. Portland and Casco Bay Area >
    2. Bailey Island Cottage
    #3001385
      (3)
      Robinhood Inn on Bailey Island Home near Sandy Beach
        7 Bedrooms,
      • 4 Bathrooms
        • , Sleeps 18
      $2,900
      per week

      Robinhood Inn on Bailey Island Home near Sandy Beach

      279 night Minimum Stay
      • 7 BR,
      • 4 BA,
      • Sleeps 18
      1. Portland and Casco Bay Area >
      2. Bailey Island House
      #120204
        (12)
        New Friendly Cottage on the Ocean with Beach
          3 Bedrooms,
        • 2 Bathrooms
          • , Sleeps 6
        $275 - $450
        per night

        New Friendly Cottage on the Ocean with Beach

        3 night Minimum Stay
        • 3 BR,
        • 2 BA,
        • Sleeps 6
        1. Portland and Casco Bay Area >
        2. Bailey Island House
        #962008
          (7)
          'The Gills' Private Oceanfront Retreat
            4 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 6
          $290
          per night

          'The Gills' Private Oceanfront Retreat

          3 - 7 night Minimum Stay
          • 4 BR,
          • 2 BA,
          • Sleeps 6
          1. Portland and Casco Bay Area >
          2. Bailey Island Cottage
          #333196
            (14)
            Ocean Front, Water Access, Air Conditioned,Near Beach, PETS FREE
              2 Bedrooms,
            • 1 Bathroom
              • , Sleeps 5
            $952 - $1,302
            per week

            Ocean Front, Water Access, Air Conditioned,Near Beach, PETS FREE

            7 night Minimum Stay
            • 2 BR,
            • 1 BA,
            • Sleeps 5
            1. Portland and Casco Bay Area >
            2. Bailey Island Cottage
            #140223
              (3)
              Wake to Sunrise on the Ocean
                4 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 7
              $1,300 - $2,000
              per week

              Wake to Sunrise on the Ocean

              7 night Minimum Stay
              • 4 BR,
              • 2 BA,
              • Sleeps 7
              1. Portland and Casco Bay Area >
              2. Bailey Island Cottage
              #106396
                (11)
                Our South Cabin offers Bold oceanfront with fantastic views!
                  Studio,
                • 1 Bathroom
                  • , Sleeps 3
                $135 - $295
                per night

                Our South Cabin offers Bold oceanfront with fantastic views!

                3 night Minimum Stay
                • Studio,
                • 1 BA,
                • Sleeps 3
                1. Portland and Casco Bay Area >
                2. Bailey Island Cottage
                #175535
                  (9)
                  Beautiful views from the Johnson Homestead, on the ocean with semi-private beach
                    4 Bedrooms,
                  • 2 Bathrooms
                    • , Sleeps 8
                  $125 - $150
                  per night

                  Beautiful views from the Johnson Homestead, on the ocean with semi-private beach

                  2 - 7 night Minimum Stay
                  • 4 BR,
                  • 2 BA,
                  • Sleeps 8
                  1. Portland and Casco Bay Area >
                  2. Bailey Island House
                  #287769
                    (7)
                    Waterfront Rental with Private Sandy Beach and Dock
                      2 Bedrooms,
                    • 1 Bathroom
                      • , Sleeps 6
                    $160 - $250
                    per night

                    Waterfront Rental with Private Sandy Beach and Dock

                    2 night Minimum Stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 6
                    1. Portland and Casco Bay Area >
                    2. Bailey Island Apartment
                    #116337
                      (14)
                      Bold Oceanfront with Breathtaking Views from our North Cabin
                        Studio,
                      • 1 Bathroom
                        • , Sleeps 3
                      $135 - $295
                      per night

                      Bold Oceanfront with Breathtaking Views from our North Cabin

                      3 night Minimum Stay
                      • Studio,
                      • 1 BA,
                      • Sleeps 3
                      1. Portland and Casco Bay Area >
                      2. Bailey Island Cottage
                      #118009
                        (36)
                        Bailey Island; Waterfront House With Spectacular Sunsets and Views
                          4 Bedrooms,
                        • 3 Bathrooms, 
                        • 1 Half Bath
                          • , Sleeps 8
                        $2,499 - $3,100
                        per week

                        Bailey Island; Waterfront House With Spectacular Sunsets and Views

                        7 night Minimum Stay
                        • 4 BR,
                        • 3 BA,
                        • 1 HF BA,
                        • Sleeps 8
                        1. Portland and Casco Bay Area >
                        2. Bailey Island House
                        #116191
                          Charming Coastal Home with Breathtaking Ocean Views, Great for the Whole Family!
                            4 Bedrooms,
                          • 3 Bathrooms
                            • , Sleeps 11
                          $200 - $250
                          per night

                          Charming Coastal Home with Breathtaking Ocean Views, Great for the Whole Family!

                          4 night Minimum Stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 11
                          1. Portland and Casco Bay Area >
                          2. Bailey Island House
                          #252488
                            Waterfront Home with Fantastic Bay and Sunset Views
                              4 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 9
                            $2,200 - $3,000
                            per week

                            Waterfront Home with Fantastic Bay and Sunset Views

                            7 night Minimum Stay
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 9
                            1. Portland and Casco Bay Area >
                            2. Bailey Island House
                            #104516
                              Owner-Designed, Sunset-facing Waterfront - June, Sept, Oct Off-Peak $985/wk
                                2 Bedrooms,
                              • 1 Bathroom
                                • , Sleeps 6
                              $985 - $1,195
                              per week

                              Owner-Designed, Sunset-facing Waterfront - June, Sept, Oct Off-Peak $985/wk

                              7 night Minimum Stay
                              • 2 BR,
                              • 1 BA,
                              • Sleeps 6
                              1. Portland and Casco Bay Area >
                              2. Bailey Island Cottage
                              #229351
                                2 Reviews
                                Charming rustic cottage on the ocean, with semi-private beach
                                  5 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 6
                                $125 - $155
                                per night

                                Charming rustic cottage on the ocean, with semi-private beach

                                3 - 7 night Minimum Stay
                                • 5 BR,
                                • 2 BA,
                                • Sleeps 6
                                1. Portland and Casco Bay Area >
                                2. Bailey Island Cottage
                                #184120
                                  (4)
                                  Charming Cottage with Water Views
                                    1 Bedrooms,
                                  • 1 Bathroom
                                    • , Sleeps 3
                                  $595 - $651
                                  per week

                                  Charming Cottage with Water Views

                                  7 night Minimum Stay
                                  • 1 BR,
                                  • 1 BA,
                                  • Sleeps 3
                                  1. Portland and Casco Bay Area >
                                  2. Bailey Island Cottage
                                  #114948
                                    Home Port Mackerel Cove Bailey Island Maine
                                      3 Bedrooms,
                                    • 2 Bathrooms
                                      • , Sleeps 6
                                    $300
                                    per night

                                    Home Port Mackerel Cove Bailey Island Maine

                                    4 - 242 night Minimum Stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                    1. Portland and Casco Bay Area >
                                    2. Bailey Island House
                                    #940196
                                      1 Review
                                      Killer Sunsets on Merriconeag Sound
                                        7 Bedrooms,
                                      • 6 Bathrooms, 
                                      • 1 Half Bath
                                        • , Sleeps 17
                                      $1,975 - $2,500
                                      per week

                                      Killer Sunsets on Merriconeag Sound

                                      7 night Minimum Stay
                                      • 7 BR,
                                      • 6 BA,
                                      • 1 HF BA,
                                      • Sleeps 17
                                      1. Portland and Casco Bay Area >
                                      2. Bailey Island House
                                      #110724
                                        Custom Amenities with Wonderful Cove and Casco Bay Views
                                          4 Bedrooms,
                                        • 5 Bathrooms
                                          • , Sleeps 10
                                        $3,995
                                        per week

                                        Custom Amenities with Wonderful Cove and Casco Bay Views

                                        7 night Minimum Stay
                                        • 4 BR,
                                        • 5 BA,
                                        • Sleeps 10
                                        1. Portland and Casco Bay Area >
                                        2. Bailey Island House
                                        #299567
                                          (8)
                                          Percy's View is a Peaceful Oceanfront Studio Cottage with a Breathtaking View
                                            1 Bedrooms,
                                          • 1 Bathroom
                                            • , Sleeps 3
                                          $800 - $1,150
                                          per week

                                          Percy's View is a Peaceful Oceanfront Studio Cottage with a Breathtaking View

                                          7 night Minimum Stay
                                          • 1 BR,
                                          • 1 BA,
                                          • Sleeps 3
                                          1. Portland and Casco Bay Area >
                                          2. Bailey Island Studio
                                          #383464
                                            2 Reviews
                                            Oceanside Tower Ultimate Comfort Lighthouse View
                                              3 Bedrooms,
                                            • 1 Bathroom, 
                                            • 1 Half Bath
                                              • , Sleeps 14
                                            $1,200 - $1,600
                                            per week

                                            Oceanside Tower Ultimate Comfort Lighthouse View

                                            7 night Minimum Stay
                                            • 3 BR,
                                            • 1 BA,
                                            • 1 HF BA,
                                            • Sleeps 14
                                            1. Portland and Casco Bay Area >
                                            2. Bailey Island House
                                            #112112
                                              1 Review
                                              Authentic maine cottage with direct water frontage
                                                3 Bedrooms,
                                              • 1 Bathroom
                                                • , Sleeps 6

                                              Authentic maine cottage with direct water frontage

                                              • 3 BR,
                                              • 1 BA,
                                              • Sleeps 6
                                              1. Portland and Casco Bay Area >
                                              2. Bailey Island Cottage
                                              #164879
                                                2 Reviews
                                                1890 Summer Cottage on an Ocean Bluff
                                                  5 Bedrooms,
                                                • 2 Bathrooms
                                                  • , Sleeps 7

                                                1890 Summer Cottage on an Ocean Bluff

                                                • 5 BR,
                                                • 2 BA,
                                                • Sleeps 7
                                                1. Portland and Casco Bay Area >
                                                2. Bailey Island Cottage
                                                #232029
                                                  (4)
                                                  Charming 1876 Restored Lobsterman's Home w/Water Views & Sunsets. Internet.
                                                    2 Bedrooms,
                                                  • 1 Bathroom
                                                    • , Sleeps 3
                                                  $650 - $700
                                                  per week

                                                  Charming 1876 Restored Lobsterman's Home w/Water Views & Sunsets. Internet.

                                                  7 night Minimum Stay
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • Sleeps 3
                                                  1. Portland and Casco Bay Area >
                                                  2. Bailey Island Cottage
                                                  #242266
                                                    (3)
                                                    'The Bungalow' Classic Maine Cottage, Bailey Island, Maine
                                                      3 Bedrooms,
                                                    • 1 Bathroom
                                                      • , Sleeps 6

                                                    'The Bungalow' Classic Maine Cottage, Bailey Island, Maine

                                                    • 3 BR,
                                                    • 1 BA,
                                                    • Sleeps 6
                                                    1. Portland and Casco Bay Area >
                                                    2. Bailey Island House
                                                    #236595
                                                      16 More choices from HomeAway International Websites
                                                      Sea Escape Penthouse
                                                        1 Bedrooms,
                                                      • 1 Bathroom
                                                        • , Sleeps 7
                                                      $175
                                                      per night

                                                      Sea Escape Penthouse

                                                      2 - 7 night Minimum Stay
                                                      • 1 BR,
                                                      • 1 BA,
                                                      • Sleeps 7
                                                      1. Portland and Casco Bay Area >
                                                      2. Bailey Island Apartment
                                                      #434903vb
                                                        1 bed/ 1 bath Waterfront cottage at head of scenic Mackerel Cove
                                                          2 Bedrooms,
                                                        • 1 Bathroom
                                                          • , Sleeps 2
                                                        $900 - $1,100
                                                        per week

                                                        1 bed/ 1 bath Waterfront cottage at head of scenic Mackerel Cove

                                                        7 night Minimum Stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 2
                                                        1. Portland and Casco Bay Area >
                                                        2. Bailey Island Cottage
                                                        #467921vb
                                                          Sea Scent - Nautical-themed cottage located on beautiful Bailey Island
                                                            2 Bedrooms,
                                                          • 1 Bathroom
                                                            • , Sleeps 4
                                                          $1,200
                                                          per week

                                                          Sea Scent - Nautical-themed cottage located on beautiful Bailey Island

                                                          7 night Minimum Stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 4
                                                          1. Portland and Casco Bay Area >
                                                          2. Bailey Island Cottage
                                                          #457805vb
                                                            Sandy beach steps away!
                                                              2 Bedrooms, Sleeps 4

                                                            Sandy beach steps away!

                                                            • 2 BR,
                                                            • Sleeps 4
                                                            1. Portland and Casco Bay Area >
                                                            2. Bailey Island Cottage
                                                            #422689vb
                                                              (7)
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