Family-Friendly Vacation Rentals in Bailey Island, ME: Compare 10+ Sites & Save

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  4.  Maine

  5.  Bailey Island

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36 Best Family Vacation Rentals in Bailey Island (Starting from $196)

Betty's Place - Cozy ocean front getaway with views of Casco Bay
Betty's Place - Cozy ocean front getaway with views of Casco Bay
House
Orrs Island, ME, USA
3.4k from Bailey Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom4 Guests
New to Booking
$196
Average price / night
Check Availability
Nicest Waterfront in Maine w/ Private Beach!
Nicest Waterfront in Maine w/ Private Beach!
House
Harpswell, ME, 04003, United States
0.8k from Bailey Island center

Arcade, Balcony, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms10 Guests
9.6

Exceptional

44 reviews

$1341
Average price / night
Check Availability
Charming Retreat with Deck about 4 Mi From Casco Bay!
Charming Retreat with Deck about 4 Mi From Casco Bay!
House
Orrs Island, ME, USA
4.3k from Bailey Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms6 Guests
New to Booking
$405
Average price / night
Check Availability
Summer Cottage
Summer Cottage
Cottage
Harpswell, ME, 04003, United States
1.3k from Bailey Island center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms8 Guests
8.8

Fabulous

8 reviews

$358
Average price / night
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Harpswell Beach House
Harpswell Beach House
House
West Harpswell, ME, USA
6.0k from Bailey Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$635
Average price / night
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The Beach House Bailey Island Maine
The Beach House Bailey Island Maine
Apartment
Harpswell, ME, 04003, United States
1.4k from Bailey Island center

Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

35 reviews

$309
Average price / night
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Clark Cove
Clark Cove
House
ME, USA
6.3k from Bailey Island center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms7 Guests
New to Booking
$648
Average price / night
Check Availability
Johnson Homestead. One level living, ocean view with semi-private beach access.
Johnson Homestead. One level living, ocean view with semi-private beach access.
House
Bailey Island, ME, 04003, United States
1.5k from Bailey Island center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.8

Exceptional

86 reviews

$488
Average price / night
Check Availability
Oceanfront Studio with Private Dock in Harpswell!
Oceanfront Studio with Private Dock in Harpswell!
Apartment
Dyer Cove, ME, USA
8.3k from Bailey Island center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$328
Average price / night
Check Availability
PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home
PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home
Cottage
Harpswell, ME, 04003, United States
1.6k from Bailey Island center

Balcony, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

62 reviews

$572
Average price / night
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Tide's Edge
Tide's Edge
House
Cundys Harbor, ME, USA
9.0k from Bailey Island center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

4 Bedrooms10 Guests
New to Booking
$2069
Average price / night
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PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Cottage
Bailey Island, ME, 04003, United States
1.7k from Bailey Island center

AC, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms12 Guests
10.0

Exceptional

107 reviews

$875
Average price / night
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Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
House
Bailey Island, ME, 04003, United States
1.7k from Bailey Island center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

6 Bedrooms14 Guests
9.8

Exceptional

81 reviews

$782
Average price / night
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Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
House
Harpswell, ME, 04103, United States
1.8k from Bailey Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
9.8

Exceptional

158 reviews

$942
Average price / night
Check Availability
Oceanfront 4 bed, 3 bath colonial beach home, right on Casco Bay!
Oceanfront 4 bed, 3 bath colonial beach home, right on Casco Bay!
House
Harpswell, ME, 04079, United States
2.6k from Bailey Island center

Arcade, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms13 Guests
9.8

Exceptional

39 reviews

$681
Average price / night
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The Beach Pea 2 BR/1 BA Beachside bungalow feet from the Maine shore.
The Beach Pea 2 BR/1 BA Beachside bungalow feet from the Maine shore.
Cottage
Harpswell, ME, 04079, United States
2.7k from Bailey Island center

Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

5 reviews

$490
Average price / night
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Brand new year-round oceanfront home with beach.
Brand new year-round oceanfront home with beach.
House
Harpswell, ME, 04079, United States
2.9k from Bailey Island center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

49 reviews

$1346
Average price / night
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Spectacular Oceanfront House on Maine Coast
Spectacular Oceanfront House on Maine Coast
House
Orrs Island, ME, 04066, United States
3.5k from Bailey Island center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms10 Guests
10.0

Exceptional

22 reviews

$1090
Average price / night
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Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove
Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove
Cottage
Orrs Island, ME, 04066, United States
3.6k from Bailey Island center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

23 reviews

$263
Average price / night
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Beautifully renovated 4BR, 2BA pet friendly home with ocean views and access
Beautifully renovated 4BR, 2BA pet friendly home with ocean views and access
House
Harpswell, ME, 04079, United States
3.7k from Bailey Island center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

4 Bedrooms10 Guests
New to Booking
$663
Average price / night
Check Availability
 Island Home Minutes Away from beaches, hiking, kayaking, or seaside dining
Island Home Minutes Away from beaches, hiking, kayaking, or seaside dining
House
Orr's Island', ME, 04066, United States
3.9k from Bailey Island center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms7 Guests
9.4

Superb

12 reviews

$427
Average price / night
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The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
House
Harpswell, ME, 04079, United States
4.0k from Bailey Island center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

6 Bedrooms15 Guests
10.0

Exceptional

2 reviews

$1053
Average price / night
Check Availability
Grace's Place, a Real Maine Cottage
Grace's Place, a Real Maine Cottage
Cottage
harpswell, ME, 04079, United States
4.1k from Bailey Island center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
9.8

Exceptional

51 reviews

$316
Average price / night
Check Availability
Waterfront Main House &  Guest Cottage- Casco Bay, So. Harpswell.
Waterfront Main House & Guest Cottage- Casco Bay, So. Harpswell.
House
Harpswell, ME, 04079, United States
4.2k from Bailey Island center

Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$365
Average price / night
Check Availability
Howard Family Cottage with Casco Bay Sunset Views!
Howard Family Cottage with Casco Bay Sunset Views!
House
Harpswell, ME, 04079, United States
4.7k from Bailey Island center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.6

Exceptional

10 reviews

$284
Average price / night
Check Availability
Private Ocean Front property with bathing cove and deep water swimming
Private Ocean Front property with bathing cove and deep water swimming
House
Harpswell, ME, 04079, United States
5.4k from Bailey Island center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.8

Exceptional

57 reviews

$280
Average price / night
Check Availability
Sunrise Catcher with a Panoramic View!
Sunrise Catcher with a Panoramic View!
House
Harpswell, ME, 04079, United States
5.7k from Bailey Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$708
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Bailey Island.

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Bailey Island Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 36 verified family-friendly vacation rentals in Bailey Island. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Bailey Island vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $196 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Bailey Island offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Bailey Island are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Bailey Island often include amenities such as Child Friendly, Balcony/Terrace, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.