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

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  4.  Florida
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  6.  Bay Island

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3844 Best 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
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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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The Seagrape Villa -Family Friendly- Luxury Accommodation in Paradise
The Seagrape Villa -Family Friendly- Luxury Accommodation in Paradise
House
Sarasota, FL, 34242, United States
0.1k from Bay Island center

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

5 Bedrooms10 Guests
10.0

Exceptional

52 reviews

$676
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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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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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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Sunny Siesta Key Retreat w/ Private Heated Pool | 2BR | Dog-Friendly
Sunny Siesta Key Retreat w/ Private Heated Pool | 2BR | Dog-Friendly
House
Siesta Key, FL, 34242, United States
0.2k from Bay Island center

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

2 Bedrooms6 Guests
New to Booking
$229
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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Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock
Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock
House
Siesta Key, FL, 34242, United States
0.3k from Bay Island center

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

4 Bedrooms10 Guests
New to Booking
$1146
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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Salty Sailfish | Private Pool + Hot Tub + Siesta Key
Salty Sailfish | Private Pool + Hot Tub + Siesta Key
House
Sarasota, FL, 34242, United States
0.3k from Bay Island center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1116
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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Siesta Key Paradise
Siesta Key Paradise
House
Sarasota, FL, 34242, United States
0.3k from Bay Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Microwave

3 Bedrooms6 Guests
6.0

Review score

1 reviews

$490
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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Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony
Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony
House
Sarasota, FL, 34242, United States
0.3k from Bay Island center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$452
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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Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
House
Siesta Key, FL, 34242, United States
0.3k from Bay Island center

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

4 Bedrooms10 Guests
9.4

Superb

37 reviews

$720
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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AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool
AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool
House
Siesta Key, FL, 34242, United States
0.3k from Bay Island center

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

5 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$1917
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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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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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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Spacious Siesta Key Home with Private Heated Pool – Pet Friendly, Near Beaches
Spacious Siesta Key Home with Private Heated Pool – Pet Friendly, Near Beaches
House
Siesta Key, FL, 34242, United States
0.4k from Bay Island center

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

3 Bedrooms9 Guests
9.0

Fabulous

53 reviews

$413
Average price / night
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Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Villa
Sarasota, FL, 34242, United States
0.4k from Bay Island center

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

7 Bedrooms14 Guests
10.0

Exceptional

10 reviews

$1963
Average price / night
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Canal-front home near Shell Beach with access to bay & deck
Canal-front home near Shell Beach with access to bay & deck
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$531
Average price / night
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Sunset West | Private Pool, Spa, Near Siesta Key Beach & Siesta Key Village
Sunset West | Private Pool, Spa, Near Siesta Key Beach & Siesta Key Village
House
Siesta Key, FL, 34242, United States
0.5k from Bay Island center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$710
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 Vacation Rentals in Bay Island.

Where to stay in Bay Island? Best neighborhoods & areas

Bay Island Vacation Rentals on the Map

Frequently Asked Questions

You can explore 3844 verified vacation rentals in Bay Island. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Bay Island vary depending on the season, property size, and location. Rates typically start from around $134 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Bay Island include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Bay Island welcome pets. Currently, 45 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Bay Island often include amenities such as Laundry, Pool, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.