Owner Direct Vacation Rentals in Oyster Bay

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4009 Oyster Bay Vacation Homes From $131

Looking for the ideal vacation rental in Oyster Bay? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Sarasota House with Backyard Oasis 6 Mi to Beach!
Sarasota House with Backyard Oasis 6 Mi to Beach!
House
Sarasota, FL, USA
0.4k from Oyster Bay center

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

2 Bedrooms4 Guests
New to Booking
$589
Average price / night
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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
7.6

Good

7 reviews

$201
Average price / night
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Mid-Century Gem
Mid-Century Gem
House
Sarasota, FL, 34231, United States
0.5k from Oyster Bay center

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

1 Bedroom4 Guests
10.0

Exceptional

7 reviews

$174
Average price / night
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Bright Sarasota Bungalow - 5 Mi to Siesta Beach!
Bright Sarasota Bungalow - 5 Mi to Siesta Beach!
House
Sarasota, FL, USA
0.5k from Oyster Bay center

Security/Safety, Sports/Activities, Internet, Ocean View, Parking, Oceanfront, View

1 Bedroom4 Guests
9.0

Fabulous

8 reviews

$317
Average price / night
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Private Cozy Sarasota Home home
Private Cozy Sarasota Home home
House
Sarasota, FL, USA
0.6k from Oyster Bay center

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

3 Bedrooms6 Guests
8.7

Fabulous

13 reviews

$177
Average price / night
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The Ivanhoe Getaway
The Ivanhoe Getaway
House
Sarasota, FL, 34231, United States
0.5k from Oyster Bay center

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

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$158
Average price / night
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Remodel House with Heated pool, patio and gas grill!
Remodel House with Heated pool, patio and gas grill!
House
Sarasota, FL, USA
0.9k from Oyster Bay center

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

4 Bedrooms10 Guests
New to Booking
$618
Average price / night
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Private Cozy Sarasota Home by RedAwning
Private Cozy Sarasota Home by RedAwning
House
Sarasota, FL, 34231, United States
0.6k from Oyster Bay center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

20 reviews

$392
Average price / night
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Florinda 3bdr/2bth 2car garage with New Pool
Florinda 3bdr/2bth 2car garage with New Pool
House
Sarasota, FL, USA
1.0k from Oyster Bay center

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

3 Bedrooms6 Guests
9.0

Fabulous

50 reviews

$352
Average price / night
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The Ivanhoe Hideaway
The Ivanhoe Hideaway
House
Sarasota, FL, 34231, United States
0.6k from Oyster Bay center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
10.0

Exceptional

8 reviews

$163
Average price / night
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Siesta on Lee - SRQ Pool Home Near Top Beaches!
Siesta on Lee - SRQ Pool Home Near Top Beaches!
House
Sarasota, FL, USA
1.0k from Oyster Bay center

View, Internet, Security/Safety, Barbecue/Outdoor Cooking, Air Conditioner, Oceanfront, Guest Services

1 Bedroom8 Guests
New to Booking
$348
Average price / night
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Robinhood Beach Villa
Robinhood Beach Villa
Villa
Sarasota, FL, 34231, United States
0.7k from Oyster Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$184
Average price / night
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Siesta Beach Getaway - Minutes to Beach, Shops, Dining
Siesta Beach Getaway - Minutes to Beach, Shops, Dining
House
Sarasota, FL, USA
1.1k from Oyster Bay center

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

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$171
Average price / night
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Peaceful Cottage Near Siesta Key Beach
Peaceful 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
9.6

Exceptional

4 reviews

$157
Average price / night
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Lovely Cottage near the Beach and Downtown Sarasota
Lovely Cottage near the Beach and Downtown Sarasota
House
Sarasota, FL, USA
1.1k from Oyster Bay center

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

2 Bedrooms4 Guests
9.5

Superb

2 reviews

$131
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
0.7k from Oyster Bay center

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

1 Bedroom6 Guests
10.0

Exceptional

2 reviews

$141
Average price / night
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Lovely Cottage - Close to Siesta, Shops & Dining
Lovely Cottage - Close to Siesta, Shops & Dining
House
Sarasota, FL, USA
1.1k from Oyster Bay center

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

2 Bedrooms4 Guests
9.4

Superb

12 reviews

$131
Average price / night
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4bed/4bath/2half bath with screened-in heated pool, 10 mins to Siesta Beach/Town
4bed/4bath/2half bath with screened-in heated pool, 10 mins to Siesta Beach/Town
House
South Sarasota, FL, 34231, United States
0.7k from Oyster Bay center

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

4 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$577
Average price / night
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Cozy house near Siesta Key Beach
Cozy house near Siesta Key Beach
House
Sarasota, FL, 34231, United States
0.7k from Oyster Bay center

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

2 Bedrooms4 Guests
10.0

Exceptional

25 reviews

$237
Average price / night
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Pool house 10 mins to Siesta Key #1 Bch
Pool house 10 mins to Siesta Key #1 Bch
House
Sarasota, FL, 34231, United States
0.8k from Oyster Bay center

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

2 Bedrooms4 Guests
New to Booking
$617
Average price / night
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Spacious 3BR Retreat • King Beds • Close to Siesta Key
Spacious 3BR Retreat • King Beds • Close to Siesta Key
House
Sarasota, FL, 34231, United States
0.8k from Oyster Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$258
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 Oyster Bay.

Where to stay in Oyster Bay? Best neighborhoods & areas

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OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Oyster Bay. If you plan on staying in the Oyster Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Oyster Bay

You can explore 4009 verified vacation rentals in Oyster 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 Oyster Bay vary depending on the season, property size, and location. Rates typically start from around $131 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 Oyster 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 Oyster Bay welcome pets. Currently, 35 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 Oyster Bay often include amenities such as Fireplace/Heating, Internet, and View. 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.