Owner Direct Oceanfront Rentals in Osprey

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida

  5.  Sarasota
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2002 Osprey Oceanfront Rentals From $60

Want the sea right at your doorstep in Osprey? Look through stunning oceanfront villas, coastal cottages, and boardwalk condos. Compare verified properties on Owner Direct to enjoy direct beach access and unhindered ocean views.

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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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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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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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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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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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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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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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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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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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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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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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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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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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
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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
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Rare private beachfront estate on the Gulf.
Rare private beachfront estate on the Gulf.
House
Nokomis, FL, 34275, United States
1.8k from Osprey center

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

5 Bedrooms8 Guests
10.0

Exceptional

23 reviews

$5438
Average price / night
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Dune walkway to water! A perfect beach bungalow, built for relaxation
Dune walkway to water! A perfect beach bungalow, built for relaxation
House
Nokomis, FL, 34275, United States
1.9k from Osprey center

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

3 Bedrooms6 Guests
9.8

Exceptional

59 reviews

$614
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 Oceanfront 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.

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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 Oceanfront Rentals in Osprey

You can explore 2002 verified oceanfront rentals in Osprey. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Osprey vary depending on the property size, exact beachfront location, and season. Rates typically start from around $60 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Osprey offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it's helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Osprey welcome pets. Currently, 42 listings allow pets, although policies can vary by property. It's recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Osprey often include features designed for a comfortable coastal stay, such as Oceanfront, View, and Fireplace/Heating. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.