Short-Term Rentals in Oyster Bay, FL: Compare 10+ Sites & Save

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5928 Best Short-Term Rentals in Oyster Bay (Starting from $131)

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
7.8

Good

6 reviews

$144
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

1 reviews

$154
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

$146
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

$257
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

$151
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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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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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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2500sqft 4bed + heated pool, 10 mins to beach/town
2500sqft 4bed + heated pool, 10 mins to 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

2 reviews

$586
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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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

23 reviews

$197
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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Coastal Contemporary in “The Landings” tennis community ~ Siesta Key.
Coastal Contemporary in “The Landings” tennis community ~ Siesta Key.
House
Sarasota, FL, 34231, United States
0.7k from Oyster Bay center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Laundry, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$465
Average price / night
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Modern, Fresh - Only 3 miles to the Beach!
Modern, Fresh - Only 3 miles to the Beach!
Apartment
Sarasota, FL, USA
1.2k from Oyster Bay center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms5 Guests
8.8

Fabulous

5 reviews

$191
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
$562
Average price / night
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Modern & Fresh - Less than 3 miles to the Beach!
Modern & Fresh - Less than 3 miles to the Beach!
House
Sarasota, FL, USA
1.2k from Oyster Bay center

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

2 Bedrooms5 Guests
8.5

Very Good

4 reviews

$259
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
New to Booking
$223
Average price / night
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Only 10 min to Siesta Key!
Only 10 min to Siesta Key!
House
Sarasota, FL, 34231, United States
0.8k from Oyster Bay center

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

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$236
Average price / night
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Cozy 1-bedroom house in pleasant Sarasota with AC
Cozy 1-bedroom house in pleasant Sarasota with AC
House
Sarasota, FL, 34231, United States
0.8k from Oyster Bay center

1 Bedroom2 Guests
10.0

Exceptional

6 reviews

$158
Average price / night
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Beautiful West of The Trail Home
Beautiful West of The Trail Home
House
Sarasota, FL, 34239, United States
0.8k from Oyster Bay center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

5 Bedrooms10 Guests
New to Booking
$749
Average price / night
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The Mango House Cozy Beach Cottage
The Mango House Cozy Beach Cottage
House
Sarasota, FL, 34231, United States
0.9k from Oyster Bay center

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

1 Bedroom5 Guests
10.0

Exceptional

5 reviews

$310
Average price / night
Check Availability
3-bedroom house in awesome Sarasota with WiFi, AC. Enjoy your stay
3-bedroom house in awesome Sarasota with WiFi, AC. Enjoy your stay
House
Sarasota, FL, 34231, United States
0.9k from Oyster Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$593
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 Short-Term Rentals in Oyster Bay.

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Oyster Bay Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 5928 verified short-term rentals in Oyster Bay, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Oyster Bay vary depending on location, property size, and travel dates. Rates typically start from around $131 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Oyster Bay include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Oyster Bay, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Oyster Bay often include amenities such as Fireplace/Heating, Internet, and View, providing a comfortable and convenient stay.

Short-term rentals in Oyster Bay are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.