Family-Friendly Vacation Rentals in Bay Island, FL: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Bay Island

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1939 Best Family Vacation Rentals in Bay Island (Starting from $134)

Family friendly with large pool
Family friendly with large pool
House
Sarasota, FL, USA
0.3k from Bay Island center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1078
Average price / night
Check Availability
Another Day in Paradise!
Another Day in Paradise!
House
Sarasota, FL, 34242, United States
0.1k from Bay Island center

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

2 Bedrooms5 Guests
10.0

Exceptional

51 reviews

$474
Average price / night
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Casa Leone - 3446
Casa Leone - 3446
House
Siesta Key, FL, USA
0.3k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$847
Average price / night
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Quiet Bohemian Home on Siesta Key
Quiet Bohemian Home on Siesta Key
House
Sarasota, FL, 34242, United States
0.2k from Bay Island center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms13 Guests
10.0

Exceptional

3 reviews

$738
Average price / night
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Siesta Dolce - 3750
Siesta Dolce - 3750
House
Siesta Key, FL, USA
0.5k from Bay Island center

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

4 Bedrooms6 Guests
New to Booking
$709
Average price / night
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Siesta Key Sports Paradise- bball, vball, tennis, pickleball
Siesta Key Sports Paradise- bball, vball, tennis, pickleball
House
Sarasota, FL, 34242, United States
0.4k from Bay Island center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$859
Average price / night
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Escape By The Sea
Escape By The Sea
House
Sarasota, FL, USA
0.5k from Bay Island center

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

2 Bedrooms6 Guests
New to Booking
$588
Average price / night
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Holiday Sunshine Savings: Luxurious Waterfront Retreat minutes from beach
Holiday Sunshine Savings: Luxurious Waterfront Retreat minutes from beach
House
Siesta Key, FL, 34242, United States
0.5k from Bay Island center

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

4 Bedrooms8 Guests
10.0

Exceptional

56 reviews

$1218
Average price / night
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Sunset West - 3360
Sunset West - 3360
House
Siesta Key, FL, USA
0.5k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$1121
Average price / night
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3 Bedroom House North End of Siesta Key - Short Walk To Shell Beach
3 Bedroom House North End of Siesta Key - Short Walk To Shell Beach
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

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

3 Bedrooms6 Guests
9.8

Exceptional

13 reviews

$370
Average price / night
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Casa Playa
Casa Playa
House
Bailey Hall, FL, USA
0.5k from Bay Island center

Sports/Activities, Pool, Security/Safety, Fireplace/Heating, Internet, Parking, Child Friendly

1 Bedroom10 Guests
New to Booking
$841
Average price / night
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Dog-friendly gated spacious Siesta Key Getaway — Pool, Spa, & Mancave.
Dog-friendly gated spacious Siesta Key Getaway — Pool, Spa, & Mancave.
House
Siesta Key, FL, 34242, United States
0.5k from Bay Island center

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

5 Bedrooms10 Guests
9.8

Exceptional

13 reviews

$984
Average price / night
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Shell Beach Home 209
Shell Beach Home 209
House
Sarasota, FL, USA
0.5k from Bay Island center

Accommodations, Pools, Villas, Vacation homes, Cottages, 4-star, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$741
Average price / night
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Stunning Siesta Key,,  .  , Walk to Shell Beach, HEATED POOL - Discounts
Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

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

5 Bedrooms14 Guests
9.8

Exceptional

128 reviews

$646
Average price / night
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Your Personal Resort-7BR, Pool, Tennis, Boating &
Your Personal Resort-7BR, Pool, Tennis, Boating &
House
Sarasota, FL, USA
0.5k from Bay Island center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

7 Bedrooms15 Guests
New to Booking
$2068
Average price / night
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Private Home in Siesta Key, Florida, USA
Private Home in Siesta Key, Florida, USA
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

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

3 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$560
Average price / night
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Brisas Del Mar
Brisas Del Mar
House
Sarasota, FL, USA
0.5k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$779
Average price / night
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Your Personal Resort-7BR-12 Beds, Pool, Bocce Ball, Boating & so much more!
Your Personal Resort-7BR-12 Beds, Pool, Bocce Ball, Boating & so much more!
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

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

7 Bedrooms14 Guests
10.0

Exceptional

11 reviews

$1153
Average price / night
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New Sky side cottage close to beach
New Sky side cottage close to beach
House
Sarasota, FL, USA
0.6k from Bay Island center

Internet, Pet Friendly, Air Conditioner, Parking, Child Friendly

1 Bedroom2 Guests
New to Booking
$134
Average price / night
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Siesta Key Vacation Property W/Heated Pool and Beach Access
Siesta Key Vacation Property W/Heated Pool and Beach Access
House
Sarasota, FL, 34242, United States
0.6k from Bay Island center

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

3 Bedrooms6 Guests
10.0

Exceptional

66 reviews

$431
Average price / night
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Palm Paradise - Pet Friendly Home on Siesta Key w/Large Heated Private Pool & Outdoor Area!
Palm Paradise - Pet Friendly Home on Siesta Key w/Large Heated Private Pool & Outdoor Area!
House
Sarasota, FL, USA
0.6k from Bay Island center

Spa, Security/Safety, Parking, Internet, Sports/Activities, Pool, Guest Services

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$728
Average price / night
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The Pink Palm on Siesta Key
The Pink Palm on Siesta Key
House
Sarasota, FL, 34242, United States
0.6k from Bay Island center

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

3 Bedrooms8 Guests
9.6

Exceptional

14 reviews

$430
Average price / night
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Shore Thing - 185
Shore Thing - 185
House
Siesta Key, FL, USA
0.6k from Bay Island center

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

5 Bedrooms11 Guests
New to Booking
$1133
Average price / night
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Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience
Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience
House
Sarasota, FL, 34236, United States
0.8k from Bay Island center

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

4 Bedrooms8 Guests
9.8

Exceptional

11 reviews

$1319
Average price / night
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Secluded Intercoastal 3BR Siesta Key retreat w/pool & water views
Secluded Intercoastal 3BR Siesta Key retreat w/pool & water views
House
Siesta Key, FL, 34242, United States
0.9k from Bay Island center

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

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$1103
Average price / night
Check Availability
SERENITY SIESTA/OLD FLORIDA FEEL/SANDY BEACH/GULF IN THE BACKYARD
SERENITY SIESTA/OLD FLORIDA FEEL/SANDY BEACH/GULF IN THE BACKYARD
House
Siesta Key, FL, 34242, United States
1.1k from Bay Island center

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

4 Bedrooms8 Guests
9.0

Fabulous

78 reviews

$588
Average price / night
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Sarasota Renovated Waterfront Home with Dock Wide Open Bay Views Heated Pool
Sarasota Renovated Waterfront Home with Dock Wide Open Bay Views Heated Pool
House
Sarasota, FL, 34239, United States
1.1k from Bay Island center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$1119
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 Bay Island.

Where to stay in Bay Island? Best neighborhoods & areas

Bay Island Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1939 verified family-friendly vacation rentals in Bay Island. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Bay Island vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $134 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Bay 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 Bay 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 Bay Island often include amenities such as Child Friendly, Laundry, and Pool. 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.