Family-Friendly Vacation Rentals in Rolling Bay Winery, WA: Compare 10+ Sites & Save

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  6.  Rolling Bay Winery

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113 Best Family Vacation Rentals in Rolling Bay Winery (Starting from $132)

Rolling Bay Villa
Rolling Bay Villa
House
WA, USA
1.1k from Rolling Bay Winery center

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

1 Bedroom7 Guests
New to Booking
$1057
Average price / night
Check Availability
Sunrise Oasis. Water View. Family & Dog friendly
Sunrise Oasis. Water View. Family & Dog friendly
House
Bainbridge Island, WA, 98110, United States
1.4k from Rolling Bay Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

37 reviews

$1093
Average price / night
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Rolling Bay Walk
Rolling Bay Walk
House
WA, USA
1.1k from Rolling Bay Winery center

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

2 Bedrooms4 Guests
8.0

Good

4 reviews

$651
Average price / night
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Bainbridge Island Abode < 1 Mi to Winslow!
Bainbridge Island Abode < 1 Mi to Winslow!
House
Bainbridge Island, WA, 98110-1783, United States
3.2k from Rolling Bay Winery center

Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, Patio, Toys

2 Bedrooms4 Guests
9.2

Superb

35 reviews

$268
Average price / night
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The Island Quarters
The Island Quarters
House
Hawley, WA, USA
3.1k from Rolling Bay Winery center

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

1 Bedroom4 Guests
New to Booking
$296
Average price / night
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UPDATED LISTING! Waterfront Beachhouse on Bainbridge Island, WA
UPDATED LISTING! Waterfront Beachhouse on Bainbridge Island, WA
House
Bainbridge Island, WA, 98110, United States
3.5k from Rolling Bay Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

106 reviews

$667
Average price / night
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Bainbridge Island Abode Less Than 1 Mi to Winslow!
Bainbridge Island Abode Less Than 1 Mi to Winslow!
House
Winslow, WA, USA
3.2k from Rolling Bay Winery center

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

2 Bedrooms4 Guests
6.0

Review score

3 reviews

$344
Average price / night
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Beautiful beachfront home
Beautiful beachfront home
House
Bainbridge Island, WA, 98110, United States
3.5k from Rolling Bay Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
New to Booking
$643
Average price / night
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Lush Garden Home - Private Gym & Ferry Access
Lush Garden Home - Private Gym & Ferry Access
House
Hawley, WA, USA
3.4k from Rolling Bay Winery center

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

2 Bedrooms8 Guests
New to Booking
$1112
Average price / night
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Stunning Beach Suite, great mountain & water views, near downtown Winslow, Cozy.
Stunning Beach Suite, great mountain & water views, near downtown Winslow, Cozy.
House
Bainbridge Island, WA, 98110, United States
3.8k from Rolling Bay Winery center

Barbecue, Crib, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

1 Bedroom4 Guests
9.6

Exceptional

206 reviews

$285
Average price / night
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Apple Tree Cottage
Apple Tree Cottage
House
Winslow, WA, USA
3.5k from Rolling Bay Winery center

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

2 Bedrooms4 Guests
New to Booking
$304
Average price / night
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Puget Sound View Estate with sprawling yard and beach access
Puget Sound View Estate with sprawling yard and beach access
House
Bainbridge Island, WA, 98110, United States
4.7k from Rolling Bay Winery center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms8 Guests
9.6

Exceptional

27 reviews

$700
Average price / night
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Central 4-Acre Cottage with Deck Walk to Bay!
Central 4-Acre Cottage with Deck Walk to Bay!
House
Manzanita, WA, USA
3.5k from Rolling Bay Winery center

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

2 Bedrooms4 Guests
9.3

Superb

3 reviews

$323
Average price / night
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Low bank waterfront on peaceful Fletcher Bay.  Perfect for families or reunions.
Low bank waterfront on peaceful Fletcher Bay. Perfect for families or reunions.
House
Bainbridge Island, WA, 98110, United States
4.7k from Rolling Bay Winery center

Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms9 Guests
10.0

Exceptional

20 reviews

$494
Average price / night
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Rosewater Cottage
Rosewater Cottage
House
Eagledale, WA, USA
4.5k from Rolling Bay Winery center

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

2 Bedrooms5 Guests
7.0

Good

1 reviews

$436
Average price / night
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Simple Living at Luxurious, Modern Farmhouse on Bainbridge Island. Dogs ok.
Simple Living at Luxurious, Modern Farmhouse on Bainbridge Island. Dogs ok.
House
Bainbridge Island, WA, 98110, United States
5.5k from Rolling Bay Winery center

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

2 Bedrooms5 Guests
10.0

Exceptional

103 reviews

$358
Average price / night
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Fletcher Bay Overlook
Fletcher Bay Overlook
House
Fletcher Bay, WA, USA
4.7k from Rolling Bay Winery center

Barbecue/Outdoor Cooking, Balcony/Terrace, Guest Services, View, Oceanfront, Fireplace/Heating, Child Friendly

3 Bedrooms6 Guests
New to Booking
$900
Average price / night
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Bainbridge Island Pebble Garden Villa Waterfront
Bainbridge Island Pebble Garden Villa Waterfront
Villa
Bainbridge Island, WA, 98110, United States
6.3k from Rolling Bay Winery center

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

4 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$1088
Average price / night
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Battle Point Paradise
Battle Point Paradise
House
WA, USA
5.2k from Rolling Bay Winery center

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

1 Bedroom2 Guests
New to Booking
$269
Average price / night
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Bainbridge Is waterfront lodge w private beach access and extensive amenities
Bainbridge Is waterfront lodge w private beach access and extensive amenities
Apartment
Bainbridge Island, WA, 98110, United States
6.7k from Rolling Bay Winery center

Arcade, Barbecue, Breakfast Available, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

6 Bedrooms12 Guests
10.0

Exceptional

16 reviews

$2102
Average price / night
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Bainbridge Tranquility
Bainbridge Tranquility
House
Madrona Heights, WA, USA
5.4k from Rolling Bay Winery center

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

3 Bedrooms6 Guests
8.5

Very Good

2 reviews

$132
Average price / night
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Luxury Waterfront Estate with Private Beach
Luxury Waterfront Estate with Private Beach
House
Poulsbo, WA, 98370, United States
6.9k from Rolling Bay Winery center

Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$1121
Average price / night
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Laid-back Luxury on Bainbridge Island air conditioned!
Laid-back Luxury on Bainbridge Island air conditioned!
House
Bainbridge Island, WA, 98110, United States
6.9k from Rolling Bay Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

92 reviews

$693
Average price / night
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Elegant PNW Waterfront Beach House with Pickleball
Elegant PNW Waterfront Beach House with Pickleball
House
Poulsbo, WA, 98370, United States
7.0k from Rolling Bay Winery center

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

4 Bedrooms9 Guests
10.0

Exceptional

5 reviews

$1210
Average price / night
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Snuggler`s Cove-Townhouse w/ Beach Access & Kayaks
Snuggler`s Cove-Townhouse w/ Beach Access & Kayaks
Villa
Bremerton, WA, 98311, United States
7.0k from Rolling Bay Winery center

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

2 Bedrooms7 Guests
10.0

Exceptional

11 reviews

$329
Average price / night
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Pleasant Beach Getaway - Breathtaking Puget Sound Views and Steps from the Beach
Pleasant Beach Getaway - Breathtaking Puget Sound Views and Steps from the Beach
House
Bainbridge Island, WA, 98110, United States
7.1k from Rolling Bay Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

128 reviews

$444
Average price / night
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5 Acre Waterfront Compound - 5 Homes, sleeping 32!
5 Acre Waterfront Compound - 5 Homes, sleeping 32!
House
Bremerton, WA, 98311, United States
7.2k from Rolling Bay Winery center

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

9 Bedrooms32 Guests
New to Booking
$1820
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 Rolling Bay Winery.

Where to stay in Rolling Bay Winery? Best neighborhoods & areas

Rolling Bay Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 113 verified family-friendly vacation rentals in Rolling Bay Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Rolling Bay Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $132 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Rolling Bay Winery 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 Rolling Bay Winery 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 Rolling Bay Winery often include amenities such as Child Friendly, Fireplace/Heating, and View. 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.