Cottage Rentals in Oyster Bay, FL: Compare 10+ Sites & Save

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66 Best Cottage Rentals in Oyster Bay (Starting from $130)

Inviting Sarasota Cottage: 5 Mi to Beach Access!
Inviting Sarasota Cottage: 5 Mi to Beach Access!
Cottage
Sarasota, FL, 34231, United States
0.5k from Oyster Bay center

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

1 Bedroom3 Guests
7.8

Good

6 reviews

$144
Average price / night
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Bright Sarasota Bungalow - 5 Mi to Siesta Beach!
Bright Sarasota Bungalow - 5 Mi to Siesta Beach!
Cottage
Sarasota, FL, 34231, United States
0.5k from Oyster Bay center

AC, Crib, Dryer, Free Parking, Kitchen, Laundry, No Smoking, Outdoor Space, Patio

2 Bedrooms5 Guests
10.0

Exceptional

34 reviews

$215
Average price / night
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Lil John Coastal Cottage Near Siesta Key Beach
Lil John Coastal Cottage Near Siesta Key Beach
Cottage
Sarasota, FL, 34231, United States
0.7k from Oyster Bay center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$165
Average price / night
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Casa Eli - Lovely Cottage
Casa Eli - Lovely Cottage
Cottage
Sarasota, FL, 34231, United States
1.1k from Oyster Bay center

AC, Dryer, Free Parking, Heater, Internet, No Smoking, Outdoor Space, Toys, TV

2 Bedrooms4 Guests
9.2

Superb

35 reviews

$193
Average price / night
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5 star Guest House heated pool on the water!
5 star Guest House heated pool on the water!
Cottage
Sarasota, FL, 34231, United States
1.3k from Oyster Bay center

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

1 Bedroom5 Guests
New to Booking
$310
Average price / night
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Studio House in Prime Location - close to Siesta Key Beach and Downtown
Studio House in Prime Location - close to Siesta Key Beach and Downtown
Cottage
Sarasota, FL, 34239, United States
1.4k from Oyster Bay center

AC, Barbecue, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
New to Booking
$147
Average price / night
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'Vintage Mermaid Cottage' 4 Mi to Siesta Key Beach
'Vintage Mermaid Cottage' 4 Mi to Siesta Key Beach
Cottage
Sarasota, FL, 34239, United States
1.5k from Oyster Bay center

AC, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Patio, TV

2 Bedrooms6 Guests
New to Booking
$189
Average price / night
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Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Cottage
Sarasota, FL, 34239, United States
2.2k from Oyster Bay center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
9.6

Exceptional

14 reviews

$156
Average price / night
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Exquisite Small Cottage  Minutes to Siesta Key
Exquisite Small Cottage Minutes to Siesta Key
Cottage
Siesta Key, FL, 34231, United States
2.2k from Oyster Bay center

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

1 Bedroom2 Guests
8.0

Good

1 reviews

$131
Average price / night
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Luxury Beach Cottage on Siesta Key: Perfect Getaway, private pool.
Luxury Beach Cottage on Siesta Key: Perfect Getaway, private pool.
Cottage
Siesta Key, FL, 34242, United States
2.3k from Oyster Bay center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.4

Superb

82 reviews

$464
Average price / night
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Cozy Cottage centrally located in beautiful Sarasota Florida.
Cozy Cottage centrally located in beautiful Sarasota Florida.
Cottage
Sarasota, FL, 34231, United States
2.3k from Oyster Bay center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Patio

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$133
Average price / night
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Welcoming spacious Beach Cottage in  Sarasota near Siesta Key  w/ Luxury Decor
Welcoming spacious Beach Cottage in Sarasota near Siesta Key w/ Luxury Decor
Cottage
Sarasota, FL, 34231, United States
2.4k from Oyster Bay center

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

2 Bedrooms6 Guests
New to Booking
$158
Average price / night
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Welcome to our cottages 1 mile from the Gorgeous White Siesta Key Beach
Welcome to our cottages 1 mile from the Gorgeous White Siesta Key Beach
Cottage
Sarasota, FL, 34231, United States
2.5k from Oyster Bay center

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

1 Bedroom3 Guests
9.2

Superb

5 reviews

$142
Average price / night
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Charming Vintage Gem in Sarasota
Charming Vintage Gem in Sarasota
Cottage
Sarasota, FL, 34231, United States
2.5k from Oyster Bay center

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

2 Bedrooms4 Guests
New to Booking
$130
Average price / night
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Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
Cottage
Sarasota, FL, 34239, United States
2.5k from Oyster Bay center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

78 reviews

$347
Average price / night
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  5 Min walk to Beach & Village, Private Pool,On the Canal
5 Min walk to Beach & Village, Private Pool,On the Canal
Cottage
Siesta Key, FL, 34242, United States
2.6k from Oyster Bay center

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

4 Bedrooms8 Guests
9.8

Exceptional

26 reviews

$523
Average price / night
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Siesta Key Village Cottage , 3 blocks to beach, Large private heated pool
Siesta Key Village Cottage , 3 blocks to beach, Large private heated pool
Cottage
Siesta Key, FL, 34242, United States
2.9k from Oyster Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

29 reviews

$485
Average price / night
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The Ashton Retreat- Vibrant and Chic Cottage 5 minutes from the Beach!
The Ashton Retreat- Vibrant and Chic Cottage 5 minutes from the Beach!
Cottage
Sarasota, FL, 34231, United States
2.9k from Oyster Bay center

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

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$193
Average price / night
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Location. 3 bedroom cottage block from beach and two blocks from Siesta Village
Location. 3 bedroom cottage block from beach and two blocks from Siesta Village
Cottage
Siesta Key, FL, 34242, United States
2.9k from Oyster Bay center

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

3 Bedrooms6 Guests
9.6

Exceptional

32 reviews

$449
Average price / night
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🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Cottage
Siesta Key, FL, 34202, United States
3.0k from Oyster Bay center

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

1 Bedroom4 Guests
9.8

Exceptional

7 reviews

$496
Average price / night
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Chic Peaceful 3BD Cottage - Walk to Siesta!
Chic Peaceful 3BD Cottage - Walk to Siesta!
Cottage
Sarasota, FL, 34231, United States
3.0k from Oyster Bay center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$224
Average price / night
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Near Siesta Key with Private Pickleball Court and Heated Saltwater Pool with Spa
Near Siesta Key with Private Pickleball Court and Heated Saltwater Pool with Spa
Cottage
Sarasota, FL, 34231, United States
3.1k from Oyster Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$429
Average price / night
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Charming Cottage Near Siesta Key Village!
Charming Cottage Near Siesta Key Village!
Cottage
Siesta Key, FL, 34242, United States
3.1k from Oyster Bay center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, Pool, TV

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$403
Average price / night
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Cozy Cottage Near Siesta Key Village!
Cozy Cottage Near Siesta Key Village!
Cottage
Siesta Key, FL, 34242, United States
3.1k from Oyster Bay center

AC, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
8.0

Good

1 reviews

$404
Average price / night
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Beach Road
Beach Road
Cottage
665 Beach Road, Siesta Key, FL, 34242, United States
3.1k from Oyster Bay center

AC, Heater, Internet, Kitchen, No Smoking, TV

New to Booking
$1298
Average price / night
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All-New, Walk to Beach & Village, Private and Cozy
All-New, Walk to Beach & Village, Private and Cozy
Cottage
Siesta Key, FL, 34242, United States
3.1k from Oyster Bay center

AC, Dryer, Free Parking, Heater, Internet, No Smoking, TV, Washer

2 Bedrooms4 Guests
New to Booking
$385
Average price / night
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Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Cottage
Sarasota, FL, 34242, United States
3.1k from Oyster Bay center

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

2 Bedrooms6 Guests
9.2

Superb

181 reviews

$548
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 Cottage Rentals in Oyster Bay.

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Frequently Asked Questions

You can explore 66 verified cottage rentals in Oyster Bay. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Oyster Bay vary based on the season, location, and amenities offered. Rates typically start from around $130 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Oyster Bay feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 28 listings in Oyster Bay welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Oyster Bay are known for their comfort and charm, often including amenities such as Fireplace/Heating, Bedding/Linens, and Laundry. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Oyster Bay are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.