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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Sarasota
  6.  Bay Island

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3516 Best Oceanfront Rentals in Bay Island (Starting from $191)

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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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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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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Heated Saltwater Pool, Breathtaking outdoor terraces, beautiful landscaping- Villa Serene Escape
Heated Saltwater Pool, Breathtaking outdoor terraces, beautiful landscaping- Villa Serene Escape
House
Bay Island, Siesta Key, Florida, USA
1.4k from Bay Island center

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

6 Bedrooms12 Guests
New to Booking
$456
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 Key home 5 min from beach
Siesta Key home 5 min from beach
House
Siesta Key, FL, USA
1.7k from Bay Island center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$482
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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Siesta Key Sanctuary
Siesta Key Sanctuary
House
FL, USA
1.9k from Bay Island center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly

3 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$367
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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Private Beach Condo On Lido Key
Private Beach Condo On Lido Key
Apartment
Sarasota, FL, USA
1.9k from Bay Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Condos

1 Bedroom6 Guests
New to Booking
$344
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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Water Front Condo - Lido Beach
Water Front Condo - Lido Beach
Apartment
Sarasota, FL, USA
1.9k from Bay Island center

Apartments, Accommodations, Parking, Lodgings, Beach, Places to stay, Accessible hotels, Condos

2 Bedrooms6 Guests
New to Booking
$540
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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#1US Siesta Key Beach Pool House
#1US Siesta Key Beach Pool House
House
Siesta Key, FL, USA
2.0k from Bay Island center

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

2 Bedrooms4 Guests
5.0

Review score

1 reviews

$250
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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Home ON Key with pool, hot tub, putting green, arcade games, bike & mins to beach!
Home ON Key with pool, hot tub, putting green, arcade games, bike & mins to beach!
House
Siesta Key, FL, USA
2.0k from Bay Island center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis

5 Bedrooms16 Guests
New to Booking
$1050
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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Modern, Fresh - Only 3 miles to the Beach!
Modern, Fresh - Only 3 miles to the Beach!
Apartment
Sarasota, FL, USA
2.2k from Bay Island center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms5 Guests
8.8

Fabulous

5 reviews

$191
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
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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
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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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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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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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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 Oceanfront Rentals in Bay Island.

Where to stay in Bay Island? Best neighborhoods & areas

Bay Island Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 3516 verified oceanfront rentals in Bay Island. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Bay Island vary depending on the property size, exact beachfront location, and season. Rates typically start from around $191 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Bay Island offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Bay Island welcome pets. Currently, 55 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Bay Island often include features designed for a comfortable coastal stay, such as Ocean View, View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.