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

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366 Best Villa Rentals in Bay Island (Starting from $166)

PRIVATE POOL OASIS BY SIESTA KEY WITH YOGA RETREAT
PRIVATE POOL OASIS BY SIESTA KEY WITH YOGA RETREAT
Villa
Sarasota, FL, USA
2.3k from Bay Island center

Internet, Air Conditioner, Pool, Parking, Kitchen, Child Friendly

2 Bedrooms4 Guests
New to Booking
$536
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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Lido Beach Villa
Lido Beach Villa
Villa
Sarasota, FL, USA
2.5k from Bay Island center

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

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$989
Average price / night
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Pool Villa 3BR/3.5BA, private pool close to Siesta Key
Pool Villa 3BR/3.5BA, private pool close to Siesta Key
Villa
Sarasota, FL, 34236, United States
2.0k from Bay Island center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$415
Average price / night
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Enchanted & peaceful Oasis 10 min away from one of the most beautiful beaches in the World Siesta key
Enchanted & peaceful Oasis 10 min away from one of the most beautiful beaches in the World Siesta key
Villa
Sarasota, FL, USA
2.9k from Bay Island center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$400
Average price / night
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Robinhood Beach Villa
Robinhood Beach Villa
Villa
Sarasota, FL, 34231, United States
2.0k from Bay Island center

Internet, Laundry, Outdoor Grill

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$218
Average price / night
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Relaxing 3BR 2Ba Oasis with Heated
Relaxing 3BR 2Ba Oasis with Heated
Villa
Sarasota, FL, USA
2.9k from Bay Island center

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

1 Bedroom6 Guests
10.0

Exceptional

2 reviews

$210
Average price / night
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Nottingham Beach Bungalow near Siesta Key
Nottingham Beach Bungalow near Siesta Key
Villa
Sarasota, FL, 34231, United States
2.0k from Bay Island center

Laundry

1 Bedroom6 Guests
10.0

Exceptional

1 reviews

$166
Average price / night
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Tranquil Court Oasis
Tranquil Court Oasis
Villa
Sarasota, FL, USA
3.0k from Bay Island center

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

6 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$1094
Average price / night
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Palm Paradise Oasis: Heated Saltwater Pool by Siesta Key
Palm Paradise Oasis: Heated Saltwater Pool by Siesta Key
Villa
Sarasota, FL, 34239, United States
2.1k from Bay Island center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$494
Average price / night
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Siesta Key Beachside Villas
Siesta Key Beachside Villas
Villa
Bay Island, Siesta Key, Florida, USA
3.2k from Bay Island center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, 3-star, Lodgings, Vacation rentals

18 Bedrooms20 Guests
8.7

Fabulous

407 reviews

$1174
Average price / night
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Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Villa
Sarasota, FL, 34231, United States
2.2k from Bay Island center

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

2 Bedrooms5 Guests
9.6

Exceptional

16 reviews

$204
Average price / night
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Siesta Key Beach Resort and Suites
Siesta Key Beach Resort and Suites
Villa
Sarasota, FL, USA
3.3k from Bay Island center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

50 Bedrooms44 Guests
8.3

Very Good

720 reviews

$368
Average price / night
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Siesta Key Waterfront Estate W Pool Privacy!
Siesta Key Waterfront Estate W Pool Privacy!
Villa
Sarasota, FL, USA
3.4k from Bay Island center

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

4 Bedrooms14 Guests
10.0

Exceptional

4 reviews

$881
Average price / night
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Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota
Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota
Villa
Sarasota, FL, 34236, United States
2.3k from Bay Island center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.2

Superb

9 reviews

$397
Average price / night
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Island House Beach Resort 10B
Island House Beach Resort 10B
Villa
Bay Island, Siesta Key, Florida, USA
3.8k from Bay Island center

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

2 Bedrooms6 Guests
8.0

Good

1 reviews

$318
Average price / night
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Lovely Lido Beach Retreat Villa
Lovely Lido Beach Retreat Villa
Villa
Sarasota, FL, 34236, United States
2.3k from Bay Island center

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

2 Bedrooms4 Guests
New to Booking
$278
Average price / night
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Island House Beach Resort 40B
Island House Beach Resort 40B
Villa
Siesta Key, FL, USA
3.8k from Bay Island center

Fireplace/Heating, Pool, Air Conditioner, Guest Services, Eco Friendly, Internet, Security/Safety

2 Bedrooms4 Guests
New to Booking
$405
Average price / night
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Cozy, Charming, Lovely Lido Key Villa - Beach down the block!
Cozy, Charming, Lovely Lido Key Villa - Beach down the block!
Villa
Sarasota, FL, 34236, United States
2.4k from Bay Island center

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

2 Bedrooms4 Guests
New to Booking
$370
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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Luxury 2 bed & 2 bath Villa. Next to Siesta Key Village and beach  access 5.
Luxury 2 bed & 2 bath Villa. Next to Siesta Key Village and beach access 5.
Villa
Siesta Key, FL, 34242, United States
3.0k from Bay Island center

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

2 Bedrooms5 Guests
10.0

Exceptional

13 reviews

$602
Average price / night
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LUXURIOUS VILLA WATERFRONT NEAR SIESTA KEY BEACH
LUXURIOUS VILLA WATERFRONT NEAR SIESTA KEY BEACH
Villa
Sarasota, FL, 34231, United States
3.1k from Bay Island center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms11 Guests
9.4

Superb

3 reviews

$584
Average price / night
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100 Yds to Beach+2 Blocks to Siesta Key Village ; Heated Pool
100 Yds to Beach+2 Blocks to Siesta Key Village ; Heated Pool
Villa
Siesta Key, FL, 34242, United States
3.1k from Bay Island center

AC, Dryer, Free Parking, Internet, Laundry, Living Area, Microwave, No Smoking, Pool

1 Bedroom4 Guests
New to Booking
$328
Average price / night
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Canal Lower-Gorgeous 3 bed 3 bath near SK Village
Canal Lower-Gorgeous 3 bed 3 bath near SK Village
Villa
Siesta Key, FL, 34242, United States
3.1k from Bay Island center

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

9.6

Exceptional

40 reviews

$937
Average price / night
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Luxury Pool & Game Retreat • Close to Beaches
Luxury Pool & Game Retreat • Close to Beaches
Villa
Sarasota, FL, 34239, United States
3.2k from Bay Island center

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

4 Bedrooms10 Guests
10.0

Exceptional

12 reviews

$567
Average price / night
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Village West in heart of Siesta
Village West in heart of Siesta
Villa
Siesta Key, FL, 34242, United States
3.2k from Bay Island center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$369
Average price / night
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In the Heart of Siesta Key Village and Steps to the #1 Beach
In the Heart of Siesta Key Village and Steps to the #1 Beach
Villa
Siesta Key, FL, 34242, United States
3.2k from Bay Island center

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

2 Bedrooms4 Guests
10.0

Exceptional

106 reviews

$386
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 Villa Rentals in Bay Island.

Where to stay in Bay Island? Best neighborhoods & areas

Bay Island Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 366 verified villa rentals in Bay Island. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Bay Island vary depending on the season, location, and amenities. Rates typically start from around $166 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Bay Island are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Bay Island.

Yes, Bay Island offers a wide range of villas ideal for group stays. Many properties include 2 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Bay Island villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Bay Island often include highly sought-after amenities such as Internet, Pool, and Wellness Facilities. These features enhance comfort and convenience, making them especially popular among travelers visiting Bay Island.

To discover top-rated villas in Bay Island, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.