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

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  2. Private Beach Vacation Rentals
  3.  USA

  4.  Florida

  5.  Sarasota

  6.  Bay Island

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32 Best Private Beach Vacation Rentals in Bay Island (Starting from $100)

Coastal Retreat near Siesta Key Beach and Downtown
Coastal Retreat near Siesta Key Beach and Downtown
House
Sarasota, FL, USA
2.3k from Bay Island center

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

2 Bedrooms4 Guests
7.0

Good

3 reviews

$288
Average price / night
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Tropical Beach Resorts
Tropical Beach Resorts
Apartment
6717 Sara Sea Circle, Siesta Key, FL, 34242, United States
6.1k from Bay Island center

AC, Barbecue, Free Parking, Housekeeping, Internet, Kitchen, Laundry, Microwave, Outdoor Space

1 Bedroom2 Guests
9.4

Superb

5396 reviews

$255
Average price / night
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Lido Beach Resort - Sarasota
Lido Beach Resort - Sarasota
Resort
Sarasota, FL, USA
2.5k from Bay Island center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

118 Bedrooms34 Guests
8.8

Fabulous

856 reviews

$319
Average price / night
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Siesta Key Village, Heated Pool, Beach Access 4 min Walk, 3bdr
Siesta Key Village, Heated Pool, Beach Access 4 min Walk, 3bdr
House
Siesta Key, FL, USA
3.2k from Bay Island center

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

3 Bedrooms10 Guests
New to Booking
$865
Average price / night
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One-of-a-kindBeach, Village, Dock & Private Pool!
One-of-a-kindBeach, Village, Dock & Private Pool!
House
Siesta Key, FL, USA
3.2k from Bay Island center

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

6 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$729
Average price / night
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Luxury, Exclusive Building, Ocean Views, and Private Rooftop Sundeck
Luxury, Exclusive Building, Ocean Views, and Private Rooftop Sundeck
House
Siesta Key, FL, USA
3.4k from Bay Island center

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

6 Bedrooms20 Guests
New to Booking
$2017
Average price / night
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Jamaica Royale #42- 3 Heated Pools On The Beach!
Jamaica Royale #42- 3 Heated Pools On The Beach!
Apartment
Sarasota, FL, USA
4.1k from Bay Island center

Internet, Ocean View, Air Conditioner, Guest Services, Security/Safety, Balcony/Terrace, Private Beach

1 Bedroom4 Guests
New to Booking
$272
Average price / night
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New, New, NEW!, 3 Pools, Right on Siesta Beach!
New, New, NEW!, 3 Pools, Right on Siesta Beach!
Apartment
Siesta Key, FL, USA
4.2k from Bay Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

2 Bedrooms4 Guests
New to Booking
$443
Average price / night
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Siesta Springs
Siesta Springs
House
Siesta Key, FL, USA
4.4k from Bay Island center

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

5 Bedrooms14 Guests
New to Booking
$1964
Average price / night
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Private Beach House
Private Beach House
House
Siesta Key, FL, USA
4.4k from Bay Island center

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

2 Bedrooms9 Guests
8.0

Good

1 reviews

$534
Average price / night
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Gulf side, spacious 1 bedroom, 1 bath, 200 steps to Crescent Beach
Gulf side, spacious 1 bedroom, 1 bath, 200 steps to Crescent Beach
Apartment
Siesta Key, FL, USA
4.5k from Bay Island center

Apartments, Accommodations, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
6.0

Review score

1 reviews

$419
Average price / night
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Siesta Key Bay View Beach Access
Siesta Key Bay View Beach Access
Villa
Siesta Key, FL, USA
4.5k from Bay Island center

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

3 Bedrooms6 Guests
7.8

Good

64 reviews

$360
Average price / night
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Beautiful property on Siesta Key
Beautiful property on Siesta Key
Villa
Siesta Key, FL, USA
4.5k from Bay Island center

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

2 Bedrooms4 Guests
8.4

Very Good

51 reviews

$250
Average price / night
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Resort at Longboat Key Club
Resort at Longboat Key Club
Resort
Bay Island, Siesta Key, Florida, USA
5.1k from Bay Island center

Accommodations, Pools, Resorts, Parking, Golf, Romantic, 4-star, Lodgings, Beach

111 Bedrooms37 Guests
8.7

Fabulous

117 reviews

$737
Average price / night
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Siesta Key Serenity 308
Siesta Key Serenity 308
Apartment
Bay Island, Siesta Key, Florida, USA
5.2k from Bay Island center

Private Beach, Air Conditioner, View, Parking, Ocean View, Kitchen, Wheelchair Accessible

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$361
Average price / night
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Sunny Siesta Key Condo with Beach Access and Pool!
Sunny Siesta Key Condo with Beach Access and Pool!
Apartment
Sarasota, FL, USA
5.2k from Bay Island center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Beach, Hot tubs, Places to stay, Beach rentals

2 Bedrooms6 Guests
New to Booking
$194
Average price / night
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Midnight Cove #532, Bayside in Siesta Key, FL
Midnight Cove #532, Bayside in Siesta Key, FL
Apartment
Siesta Key, FL, USA
5.5k from Bay Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

2 Bedrooms4 Guests
7.4

Good

11 reviews

$235
Average price / night
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Midnight Cove #714, Bayside in Siesta Key, FL
Midnight Cove #714, Bayside in Siesta Key, FL
Apartment
Siesta Key, FL, USA
5.5k from Bay Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Family

2 Bedrooms4 Guests
9.0

Fabulous

7 reviews

$197
Average price / night
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6415 Midnight Pass #903
6415 Midnight Pass #903
House
Siesta Key, FL, USA
5.6k from Bay Island center

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

2 Bedrooms4 Guests
New to Booking
$252
Average price / night
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Bright 2 bedroom 2 bath condo with pool
Bright 2 bedroom 2 bath condo with pool
Apartment
Sarasota, FL, USA
5.7k from Bay Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

2 Bedrooms4 Guests
8.0

Good

1 reviews

$100
Average price / night
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Siesta Breakers #603, Gulfside in Siesta Key, FL
Siesta Breakers #603, Gulfside in Siesta Key, FL
Apartment
Siesta Key, FL, USA
5.8k from Bay Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Family

2 Bedrooms6 Guests
9.3

Superb

11 reviews

$301
Average price / night
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Sea Crest
Sea Crest
Apartment
Sarasota, FL, USA
5.9k from Bay Island center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Beach, Places to stay

24 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$235
Average price / night
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Trendy & Relaxing - Close to Beach - Pool - Hot Tub
Trendy & Relaxing - Close to Beach - Pool - Hot Tub
Apartment
Sarasota, FL, USA
5.9k from Bay Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Hot tubs, Places to stay

3 Bedrooms12 Guests
New to Booking
$760
Average price / night
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Sienna Park
Sienna Park
Apartment
Sarasota, FL, USA
6.0k from Bay Island center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Beach, Places to stay

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$148
Average price / night
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Casita West
Casita West
House
Point O'Rocks, FL, USA
6.0k from Bay Island center

Ocean View, View, Sports/Activities, Pool, Private Beach, Security/Safety, Fireplace/Heating

1 Bedroom4 Guests
New to Booking
$303
Average price / night
Check Availability
Casita East
Casita East
House
Point O'Rocks, FL, USA
6.0k from Bay Island center

Ocean View, View, Sports/Activities, Pool, Private Beach, Security/Safety, Fireplace/Heating

1 Bedroom4 Guests
New to Booking
$307
Average price / night
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Tropical Beach Resorts - Sarasota
Tropical Beach Resorts - Sarasota
Resort
Sarasota, FL, USA
6.1k from Bay Island center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Beach, Places to stay

86 Bedrooms56 Guests
9.0

Fabulous

1606 reviews

$235
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 Private Beach Vacation Rentals in Bay Island.

Where to stay in Bay Island? Best neighborhoods & areas

Bay Island Private Beach Vacation Rentals on the Map

Frequently Asked Questions

You can explore 32 verified private beach vacation rentals in Bay Island. These include secluded coastal homes and estates that offer direct beach access with a higher level of privacy.

Prices for private beach rentals in Bay Island vary depending on the property size, location, and level of beach access. Rates typically start from around $100 per night, with higher prices for larger homes or properties located on more exclusive stretches of coastline.

A private beach rental typically provides direct access to a stretch of sand that is limited to guests or nearby residents. Access levels can vary by location, so reviewing property details can help you understand how secluded the beach area is.

Yes, some private beach rentals in Bay Island welcome pets. Currently, 5 listings allow pets, although policies may vary. It’s also important to check local beach regulations for any seasonal or area-specific restrictions.

Private beach properties are often limited in number and in high demand, so booking 90 to 150 days in advance is recommended for the best selection. Planning early increases your chances of securing a more secluded and desirable property.

Private beach rentals in Bay Island often include amenities such as View, Ocean View, and Child Friendly. These features enhance comfort and allow guests to enjoy a more private and relaxing coastal stay.

Yes, there is a difference. "Oceanfront" means the property is located directly by the water, while "Private Beach" typically indicates that access to the beach area is restricted or less crowded. This distinction is important for travelers seeking a quieter and more exclusive beach experience.