Short-Term Rentals in Bay Island, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Bay Island

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5818 Best Short-Term 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
Check Availability
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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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
Check Availability
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
Beachside Private Vacation Home w/ Large Heated Pool
Beachside Private Vacation Home w/ Large Heated Pool
House
Sarasota, FL, 34242, United States
0.5k from Bay Island center

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

3 Bedrooms6 Guests
9.4

Superb

54 reviews

$443
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 Short-Term Rentals in Bay Island.

Where to stay in Bay Island? Best neighborhoods & areas

Bay Island Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 5818 verified short-term rentals in Bay Island, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Bay Island vary depending on location, property size, and travel dates. Rates typically start from around $134 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Bay Island include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Bay Island, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Bay Island often include amenities such as Laundry, Pool, and Internet, providing a comfortable and convenient stay.

Short-term rentals in Bay Island are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.