Owner Direct Beach Rentals in Osprey

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  2. Beach Rentals
  3.  USA

  4.  Florida

  5.  Sarasota
  6.  Osprey

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2550 Osprey Beach Rentals From $60

Ready for a sun-soaked trip to Osprey? Explore our index of beach house rentals and sunny coastal apartments. Owner Direct helps you filter through verified seaside options to find your next relaxing shore retreat.

Windsor Lodge Unit 3 close to the Beaches Siesta Key
Windsor Lodge Unit 3 close to the Beaches Siesta Key
Apartment
Osprey, FL, USA
1.4k from Osprey center

Apartments, Accommodations, Pools, Parking, Cabins, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.0

Fabulous

1 reviews

$206
Average price / night
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Charming Osprey Home
Charming Osprey Home
House
Osprey, FL, 34229, United States
0.2k from Osprey center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$302
Average price / night
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Windsor Lodge Unit #19, studio close to beaches
Windsor Lodge Unit #19, studio close to beaches
Apartment
Osprey, FL, USA
1.4k from Osprey center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$223
Average price / night
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Sarasota Home With Pool
Sarasota Home With Pool
House
Osprey, FL, 34229, United States
0.2k from Osprey center

AC, Arcade, Dryer, Internet, Kitchen, Living Area, No Smoking, Pool, Toys

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$288
Average price / night
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Osprey Coastal Retreat Near Siesta Key
Osprey Coastal Retreat Near Siesta Key
House
Osprey, FL, USA
2.6k from Osprey center

View, Sports/Activities, Guest Services, Internet, Fireplace/Heating, Parking, Balcony/Terrace

3 Bedrooms8 Guests
New to Booking
$85
Average price / night
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Sunny Coastal Escape
Sunny Coastal Escape
House
Osprey, FL, 34229, United States
0.3k from Osprey center

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

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$217
Average price / night
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Paradise with a pool, pier and private beach area
Paradise with a pool, pier and private beach area
Villa
Osprey, FL, USA
3.1k from Osprey center

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

5 Bedrooms12 Guests
8.0

Good

1 reviews

$706
Average price / night
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Furnished and meticulous!  Near Nokomis, Venice and Siesta Beaches.
Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
Condo
Osprey, FL, 34229, United States
0.3k from Osprey center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$244
Average price / night
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Florida Vacation Condo
Florida Vacation Condo
Apartment
Sarasota, FL, USA
3.7k from Osprey center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$60
Average price / night
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Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
House
Osprey, FL, 34229, United States
0.6k from Osprey center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
8.8

Fabulous

30 reviews

$235
Average price / night
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Turtle Beach Resort
Turtle Beach Resort
Resort
Siesta Key, FL, USA
3.9k from Osprey center

Accommodations, Pools, Resorts, Parking, Pet-friendly, 4-star, Lodgings, Hot tubs, Places to stay

20 Bedrooms44 Guests
9.0

Fabulous

77 reviews

$454
Average price / night
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Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!
Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!
House
Osprey, FL, 34229, United States
0.6k from Osprey center

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

2 Bedrooms4 Guests
New to Booking
$158
Average price / night
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The Sea Side Villa
The Sea Side Villa
House
Sarasota, FL, USA
3.9k from Osprey center

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

2 Bedrooms4 Guests
New to Booking
$237
Average price / night
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Cozy beach bungalow
Cozy beach bungalow
House
Osprey, FL, 34229, United States
0.8k from Osprey center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$256
Average price / night
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Siesta Keys Home with Deck Half Mile to Turtle Beach
Siesta Keys Home with Deck Half Mile to Turtle Beach
Apartment
Siesta Key, FL, USA
4.0k from Osprey center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Beach rentals, Condos

2 Bedrooms4 Guests
New to Booking
$295
Average price / night
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Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
House
Osprey, FL, 34229, United States
0.9k from Osprey center

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

2 Bedrooms5 Guests
10.0

Exceptional

5 reviews

$307
Average price / night
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Villa in Osprey that sleeps the whole family
Villa in Osprey that sleeps the whole family
Apartment
Osprey, FL, 34229, United States
1.0k from Osprey center

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

2 Bedrooms5 Guests
9.8

Exceptional

36 reviews

$160
Average price / night
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Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis
Condo
Osprey, FL, 34229, United States
1.2k from Osprey center

AC, Balcony, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom3 Guests
10.0

Exceptional

2 reviews

$133
Average price / night
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Enjoy this Condo Hideaway Casey Key area of Sarasota Relax and Enjoy this Secret
Enjoy this Condo Hideaway Casey Key area of Sarasota Relax and Enjoy this Secret
Condo
Osprey, FL, 34229, United States
1.2k from Osprey center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$152
Average price / night
Check Availability
Spacious 3-BR + large den condo in private, quiet luxury Casey Key area
Spacious 3-BR + large den condo in private, quiet luxury Casey Key area
Condo
Osprey, FL, 34229, United States
1.3k from Osprey center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
New to Booking
$258
Average price / night
Check Availability
Idyllic Casey Key Beach House
Idyllic Casey Key Beach House
House
Osprey, FL, 34229, United States
1.8k from Osprey center

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

3 Bedrooms6 Guests
9.6

Exceptional

37 reviews

$769
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 Beach Rentals in Osprey.

Stay Near Osprey's Top Attractions

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

Osprey Beach Rentals on the Map

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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 Osprey. If you plan on staying in the Osprey area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Rentals in Osprey

You can explore 2550 verified beach rentals in Osprey. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Osprey vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $60 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Osprey offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Osprey welcome pets. Currently, 42 listings allow pets, although policies may vary by property. It's also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it's recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Osprey often include amenities designed for coastal living, such as View, Ocean View, and Fireplace/Heating. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It's best to review the amenities section of each listing to confirm what is included and plan accordingly.