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

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3621 Best Vacation Rentals in Buccaneer Bay (Starting from $117)

Luxe Bayfront Sarasota Home Rental Pool, Lanai!
Luxe Bayfront Sarasota Home Rental Pool, Lanai!
House
Sarasota, FL, USA
0.4k from Buccaneer Bay center

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

3 Bedrooms6 Guests
New to Booking
$853
Average price / night
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\"West of Trail\" home close to Crescent Beach and Siesta Key with water access
\"West of Trail\" home close to Crescent Beach and Siesta Key with water access
House
Sarasota, FL, 34231, United States
0.2k from Buccaneer Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$370
Average price / night
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Sarasota Vacation Rental with Pool and Game Room!
Sarasota Vacation Rental with Pool and Game Room!
House
Sarasota, FL, USA
0.6k from Buccaneer Bay center

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

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$246
Average price / night
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Tropical Paradise Close To The Beaches
Tropical Paradise Close To The Beaches
House
Sarasota, FL, 34231, United States
0.3k from Buccaneer Bay center

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

3 Bedrooms8 Guests
9.6

Exceptional

41 reviews

$238
Average price / night
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4 Mi to Siesta Key Beach Sunny Home with Hot Tub!
4 Mi to Siesta Key Beach Sunny Home with Hot Tub!
House
Sarasota, FL, USA
0.8k from Buccaneer Bay center

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

2 Bedrooms6 Guests
8.0

Good

1 reviews

$397
Average price / night
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Sunset Cove - Saltwater private Pool - 1.5 miles from Siesta Key Beach
Sunset Cove - Saltwater private Pool - 1.5 miles from Siesta Key Beach
House
Sarasota, FL, 34231, United States
0.4k from Buccaneer Bay center

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

4 Bedrooms8 Guests
10.0

Exceptional

32 reviews

$539
Average price / night
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Getaway with Heated Pool and fence by Siesta Key Beach
Getaway with Heated Pool and fence by Siesta Key Beach
House
Sarasota, FL, USA
0.9k from Buccaneer Bay center

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

6 Bedrooms15 Guests
9.5

Superb

2 reviews

$633
Average price / night
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Cozy beach house: 8 minutes to your ultimate tropical getaway in Sarasota! 🌴☀️
Cozy beach house: 8 minutes to your ultimate tropical getaway in Sarasota! 🌴☀️
House
Sarasota, FL, 34231, United States
0.4k from Buccaneer Bay center

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

2 Bedrooms4 Guests
10.0

Exceptional

27 reviews

$236
Average price / night
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Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach
Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach
House
Siesta Key, FL, USA
1.1k from Buccaneer Bay center

Security/Safety, Air Conditioner, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$117
Average price / night
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Coastal Cottage
Coastal Cottage
House
Sarasota, FL, USA
1.2k from Buccaneer Bay center

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

2 Bedrooms6 Guests
New to Booking
$402
Average price / night
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Relax at Starfish Contemporary Home | Pool | Bring the entire Family - Dog Friendly | Game Room
Relax at Starfish Contemporary Home | Pool | Bring the entire Family - Dog Friendly | Game Room
House
Sarasota, FL, 34231, United States
0.4k from Buccaneer Bay center

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

3 Bedrooms8 Guests
9.8

Exceptional

8 reviews

$322
Average price / night
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Tiny House Siesta
Tiny House Siesta
House
Sarasota, FL, USA
1.2k from Buccaneer Bay center

Cheap, Accommodations, Parking, Villas, Vacation homes, Romantic, Cottages, Pet-friendly, Lodgings

27 Bedrooms63 Guests
8.3

Very Good

635 reviews

$155
Average price / night
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Shared Dock and Private Backyard with Pool -Casa Mango
Shared Dock and Private Backyard with Pool -Casa Mango
House
Sarasota, FL, 34231, United States
0.4k from Buccaneer Bay center

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

3 Bedrooms10 Guests
8.0

Good

1 reviews

$292
Average price / night
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Fantastic Island House 1 mile to the beach with heated pool
Fantastic Island House 1 mile to the beach with heated pool
House
Buccaneer Bay, Sarasota, Florida, USA
1.2k from Buccaneer Bay center

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

3 Bedrooms10 Guests
8.3

Very Good

22 reviews

$188
Average price / night
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Sarasota 2 Bedroom House right next to Siesta Key
Sarasota 2 Bedroom House right next to Siesta Key
House
Sarasota, FL, 34232, United States
0.5k from Buccaneer Bay center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$261
Average price / night
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Beachside Bliss 1 miles to the beach with heated pool
Beachside Bliss 1 miles to the beach with heated pool
Apartment
Sarasota, FL, USA
1.2k from Buccaneer Bay center

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

1 Bedroom3 Guests
9.2

Superb

6 reviews

$468
Average price / night
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Charming 1-bedroom upstairs apartment in private Sarasota Community.
Charming 1-bedroom upstairs apartment in private Sarasota Community.
Apartment
Sarasota, FL, 34231, United States
0.6k from Buccaneer Bay center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

1 Bedroom2 Guests
New to Booking
$144
Average price / night
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Sarasota Seascape
Sarasota Seascape
House
FL, USA
1.3k from Buccaneer Bay center

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

3 Bedrooms7 Guests
New to Booking
$361
Average price / night
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Luxury Home w/ Private Heated Pool, Cabana, BBQ | Near Siesta Key Beach | RV/Boat Parking Available!
Luxury Home w/ Private Heated Pool, Cabana, BBQ | Near Siesta Key Beach | RV/Boat Parking Available!
House
Sarasota, FL, 34231, United States
0.6k from Buccaneer Bay center

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

3 Bedrooms7 Guests
8.8

Fabulous

6 reviews

$294
Average price / night
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Siesta Sol Art Bungalow- 2 miles to Siesta Key!
Siesta Sol Art Bungalow- 2 miles to Siesta Key!
House
Sarasota, FL, USA
1.3k from Buccaneer Bay center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$200
Average price / night
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New 2b/2b home w/ a heated pool & hot tub near Siesta
New 2b/2b home w/ a heated pool & hot tub near Siesta
House
Sarasota, FL, 34231, United States
0.6k from Buccaneer Bay center

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

2 Bedrooms5 Guests
10.0

Exceptional

5 reviews

$443
Average price / night
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Casita Sun Star - 1135
Casita Sun Star - 1135
House
Siesta Key, FL, USA
1.4k from Buccaneer Bay center

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

3 Bedrooms10 Guests
8.0

Good

1 reviews

$1221
Average price / night
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Sarasota Vacation Rental w/ Pool & Game Room!
Sarasota Vacation Rental w/ Pool & Game Room!
House
Sarasota, FL, 34231-4713, United States
0.6k from Buccaneer Bay center

AC, Arcade, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$338
Average price / night
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Beachside Bliss: Family House-Siesta Key-3BR/2BA
Beachside Bliss: Family House-Siesta Key-3BR/2BA
House
Sarasota, FL, 34231, United States
0.6k from Buccaneer Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$394
Average price / night
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Charming 2bd 2ba, very green, 3 min drive to SiestaKey, 55+community, nice pool.
Charming 2bd 2ba, very green, 3 min drive to SiestaKey, 55+community, nice pool.
House
Sarasota, FL, 34231, United States
0.7k from Buccaneer Bay center

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

2 Bedrooms2 Guests
10.0

Exceptional

1 reviews

$167
Average price / night
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Newly remodeled POOL home minutes to Siesta Key Beach!!!
Newly remodeled POOL home minutes to Siesta Key Beach!!!
House
Sarasota, FL, 34231, United States
0.7k from Buccaneer Bay center

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

2 Bedrooms4 Guests
9.4

Superb

29 reviews

$310
Average price / night
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2BR Retreat - Private Pool Near Siesta Key
2BR Retreat - Private Pool Near Siesta Key
House
Sarasota, FL, 34231, United States
0.8k from Buccaneer Bay center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$450
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 Buccaneer Bay.

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Frequently Asked Questions

You can explore 3621 verified vacation rentals in Buccaneer Bay. 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 Buccaneer Bay vary depending on the season, property size, and location. Rates typically start from around $117 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 Buccaneer Bay 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 Buccaneer Bay welcome pets. Currently, 42 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 Buccaneer Bay often include amenities such as Fireplace/Heating, View, and Pool. 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.