Vacation Rentals in Osprey, FL
PRICE PER NIGHT
ACCOMMODATION TYPES
Florida Retreat, BBQ & Patio, Close to Beach
No reviews
·
Osprey
·
2 br
·
Sleeps 6
·
Free Parking · Balcony · Beach ·
From
$334/nightProperty
House · 2 Beds · 2 baths
Amenities
Free Parking
Beach
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Newly Remodeled Palm Villa
9.5
Excellent
·
Osprey
·
2 br
·
Sleeps 5
·
Deck · Balcony · Beach ·
From
$145/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Beach
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Deck, Balcony, Kitchen
Stoneybrook Golf & CC
No reviews
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Hot Tub · Outdoor Space · Beach ·
From
$75/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hot Tub
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Canal front home in Osprey-30 day minimum rental
No reviews
·
Osprey
·
3 br
·
Sleeps 8
·
Private Pool · Waterfront · Balcony ·
From
$175/nightProperty
House · 3 Beds · 2 baths
Amenities
Private Pool
Waterfront
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
8.9
Very good
·
Osprey
·
4 br
·
Sleeps 8
·
Fireplace · Walk In Closets · Hot Tub ·
From
$193/nightProperty
House · 4 Beds · 2 baths
Amenities
Fireplace
Walk In Closets
Hot Tub
Private Pool
Beach
Dishwasher
Pool
Oven
Other spaces
Workspace, Kitchen
Remodeled Waterfront Cottage
No reviews
·
Osprey
·
2 br
·
Walk In Closets · Dishwasher · Oven ·
From
$95/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Walk In Closets
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
COMFY COZY PLACE
9.4
Excellent
·
Osprey
·
1 br
·
Sleeps 2
·
Outdoor Space · Oven · In Unit Laundry ·
From
$85/nightProperty
House · 1 Bed · 1 bath
Amenities
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Residents Lounge
Other spaces
Kitchen
Spacious home with private pool, spa, two living rooms, fast WiFi, office & AC
No reviews
·
Osprey
·
3 br
·
Sleeps 10
·
On Site Laundry · Private Pool · Fitness Center ·
From
$348/nightProperty
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Private Pool
Fitness Center
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Other spaces
Kitchen
The best of Zumper, delivered
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Enjoy Your Own Private Oasis/Beach, Pool, Onsite Amenities, Fishing
9.1
Excellent
·
Osprey
·
2 br
·
Sleeps 5
·
Smoking Allowed · Hot Tub · Private Pool ·
From
$399/nightProperty
House · 2 Beds · 2 baths
Amenities
Smoking Allowed
Hot Tub
Private Pool
Waterfront
Fitness Center
Beach
Pool
Oven
Other spaces
Balcony, Kitchen
Private Houseboat, Waterfront, Pool, Incredible fishing, Come Relax!
9.1
Excellent
·
Osprey
·
2 br
·
Sleeps 6
·
Smoking Allowed · Hot Tub · Private Pool ·
From
$298/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Smoking Allowed
Hot Tub
Private Pool
Waterfront
Fitness Center
Beach
Pool
Oven
Other spaces
Balcony, Kitchen
Waterfront, Multiple Outdoor Porches, Beach w/ Fire pit, BBQ Area, Come Relax!
9.4
Excellent
·
Osprey
·
2 br
·
Sleeps 6
·
Smoking Allowed · Hot Tub · Private Pool ·
From
$399/nightProperty
House · 2 Beds · 2 baths
Amenities
Smoking Allowed
Hot Tub
Private Pool
Waterfront
Fitness Center
Beach
Pool
Oven
Other spaces
Kitchen
70-Foot Houseboat, Secluded Beach, Onsite Bikes & Golf carts to tour the Key!
7.6
Very good
·
Osprey
·
2 br
·
Sleeps 8
·
Smoking Allowed · Hot Tub · Waterfront ·
From
$399/nightProperty
House · 2 Beds · 2 baths
Amenities
Smoking Allowed
Hot Tub
Waterfront
Fitness Center
Beach
Pool
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Two Bedroom, Two Bath First Floor Condo
No reviews
·
Osprey
·
2 br
·
Sleeps 4
·
Workspace · Outdoor Space · Balcony ·
From
$156/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Residents Lounge
Other spaces
Workspace, Balcony, Kitchen
Beautiful home on an 18 holes golf course
10
Excellent
·
Stoneybrook Golf and Country Club
·
4 br
·
Sleeps 8
·
Private Pool · Outdoor Space · Dishwasher ·
From
$325/nightProperty
House · 4 Beds · 3 baths
Amenities
Private Pool
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Welcome to Lime on Green
10
Excellent
·
Osprey
·
2 br
·
Sleeps 5
·
Smoking Allowed · Beach · Oven ·
From
$209/nightProperty
House · 2 Beds · 1 bath
Amenities
Smoking Allowed
Beach
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
3 Bedroom Penthouse with Stunning Sunset Views of Blackburn Bay!
10
Excellent
·
Osprey
·
3 br
·
Sleeps 6
·
Assigned Parking · Walk In Closets · Balcony ·
From
$399/nightProperty
Condo · 3 Beds · 2 baths
Amenities
Assigned Parking
Walk In Closets
Pool
Wifi
Air Conditioning
Furnished
Garage Parking
Swimming Pool
Other spaces
Balcony
Florida Breeze, Private Villa Near Beach
No reviews
·
Osprey
·
2 br
·
Sleeps 6
·
Free Parking · Balcony · Dishwasher ·
From
$583/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Free Parking
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Business Center
Other spaces
Balcony, Kitchen
Cabana Royal with swimming pool!
8.4
Very good
·
Osprey
·
1 br
·
Sleeps 2
·
Smoking Allowed · Private Pool · Beach ·
From
$129/nightProperty
House · 1 Bed · 1 bath
Amenities
Smoking Allowed
Private Pool
Beach
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Siesta Key Beach Sunsets Awaits You
10
Excellent
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Workspace · Outdoor Space · Beach ·
From
$158/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Charming 2 BD Home 6 Miles From Beach
No reviews
·
Osprey
·
2 br
·
Sleeps 6
·
Free Parking · Dishwasher · Oven ·
From
$226/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Free Parking
Dishwasher
Oven
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Casey Key Resorts - Mainland
7.9
Very good
·
Osprey
·
1 br
·
Sleeps 4
·
Assigned Parking · Free Parking · On Site Laundry ·
From
$135/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Free Parking
On Site Laundry
Pool
Wifi
Air Conditioning
Furnished
Residents Lounge
Other spaces
Workspace
Spacious Condo available for short term leasing, near Siesta Key and Nokomis Bch
No reviews
·
Stoneybrook Golf and Country Club
·
3 br
·
Sleeps 4
·
Dishwasher · Pool · Oven ·
From
$150/nightProperty
Condo · 3 Beds · 2 baths
Amenities
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
Comfortable Private Master Suite in pet/smoke free house share with prof. fem.
8
Very good
·
Osprey
·
1 br
·
Sleeps 2
·
On Site Laundry · Walk In Closets · Workspace ·
From
$99/nightProperty
House · 1 Bed · 1 bath
Amenities
On Site Laundry
Walk In Closets
Fitness Center
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Other spaces
Workspace, Balcony, Kitchen
NEW 2 Bedroom with King Bed Close to Beach
No reviews
·
Osprey
·
1 br
·
Sleeps 6
·
Free Parking · Dishwasher · Oven ·
From
$560/nightProperty
Apartment · 1 Bed
Amenities
Free Parking
Dishwasher
Oven
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Gorgeous 2 Bedroom Condo w/ hot tub--- 5 Minutes from the Beach
10
Excellent
·
Osprey
·
2 br
·
Sleeps 5
·
Pool · In Unit Laundry · Wifi ·
From
$259/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Beautiful 3 Bedroom Penthouse --- 5 Minutes to the beach!
No reviews
·
Osprey
·
3 br
·
Sleeps 6
·
Pool · In Unit Laundry · Wifi ·
From
$375/nightProperty
Condo · 3 Beds · 3 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Excellent Sarasota Location In Gated Stoneybrook Golf Community
No reviews
·
Stoneybrook Golf and Country Club
·
3 br
·
Sleeps 4
·
Hot Tub · Private Pool · Workspace ·
From
$127/nightProperty
House · 3 Beds · 2 baths
Amenities
Hot Tub
Private Pool
Fitness Center
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Other spaces
Workspace, Kitchen
Ground floor lake view heated pool
No reviews
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Lake · Waterfront · Beach ·
From
$450/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Lake
Waterfront
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Other spaces
Kitchen
Ground floor Lake view 2 bed 2 bath Pool tennis Pickle ball Gated community
No reviews
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Assigned Parking · Lake · Waterfront ·
From
$450/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Assigned Parking
Lake
Waterfront
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Luxury home in beautiful waterfront community near Siesta Key and Venice beaches
7
Very good
·
Osprey
·
2 br
·
Sleeps 5
·
Private Pool · Waterfront · Fitness Center ·
From
$250/nightProperty
House · 2 Beds · 2 baths
Amenities
Private Pool
Waterfront
Fitness Center
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Other spaces
Kitchen
Tranquil Renovated 2 BDR Condo Near Beach
No reviews
·
Osprey
·
2 br
·
Sleeps 4
·
Walk In Closets · Workspace · Fitness Center ·
From
$175/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Walk In Closets
Fitness Center
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Balcony, Kitchen
Cozy and Peaceful Condo *King Bed*
No reviews
·
Osprey
·
1 br
·
Sleeps 4
·
Workspace · Outdoor Space · Balcony ·
From
$130/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Workspace, Balcony, Kitchen
2bd/2ba Condo, Pool, Gym, Pickleball, Tennis, walk to Gulf, restaurants, shop
No reviews
·
Osprey
·
2 br
·
Sleeps 4
·
Workspace · Fitness Center · Outdoor Space ·
From
$149/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Fitness Center
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Balcony, Kitchen
Quiet Location in Gated Community - Close to Beaches and Restaurants
No reviews
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Beach · Dishwasher · Pool ·
From
$140/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Gulf breezes in 2 bedroom tropical oasis - 10 min from beach!
No reviews
·
Osprey
·
2 br
·
Sleeps 4
·
On Site Laundry · Walk In Closets · Fitness Center ·
From
$126/nightProperty
Condo · 2 Beds · 2 baths
Amenities
On Site Laundry
Walk In Closets
Fitness Center
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Waterview-Condo - WiFi, Shared Pool, Hot Tub, Golf & Tennis - Snowbirds Welcome
No reviews
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 6
·
Lake · On Site Laundry · Hot Tub ·
From
$118/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Lake
On Site Laundry
Hot Tub
Waterfront
Fitness Center
Dishwasher
Pool
Oven
Other spaces
Balcony, Kitchen
Beautiful 2 Br. Single_family (366596) by Houzlet
No reviews
·
Osprey
·
2 br
·
Sleeps 4
·
Assigned Parking · Walk In Closets · Balcony ·
From
$349/nightProperty
House · 2 Beds · 2 baths
Amenities
Assigned Parking
Walk In Closets
Dishwasher
Pool
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Beautiful 2 Br. Single_family (319590) by Houzlet
No reviews
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
On Site Laundry · Dishwasher · Pool ·
From
$155/nightProperty
House · 2 Beds · 3 baths
Amenities
On Site Laundry
Dishwasher
Pool
Oven
In Unit Laundry
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
WATERFRONT Luxury Home! Private Pool, Dock, Close to Beaches
10
Excellent
·
Osprey
·
3 br
·
Sleeps 6
·
Ocean · Lake · Private Pool ·
From
$468/nightProperty
House · 3 Beds · 3 baths
Amenities
Ocean
Lake
Private Pool
Waterfront
Fitness Center
Dishwasher
Pool
Oven
Other spaces
Workspace, Kitchen
Beautiful 2 Br. Condo (20843) by Houzlet
No reviews
·
Sarabay Acres
·
2 br
·
Sleeps 4
·
Carpet · High Ceilings · Beach ·
From
$150/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Carpet
High Ceilings
Beach
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
Country Club Living close to Siesta Key Beach
10
Excellent
·
Stoneybrook Golf and Country Club
·
3 br
·
Sleeps 5
·
Workspace · Dishwasher · Pool ·
From
$110/nightProperty
Condo · 3 Beds · 2 baths
Amenities
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace, Kitchen
5 star upscale 1 bed condo near Siesta Key Beach!
No reviews
·
Osprey
·
1 br
·
Sleeps 4
·
Ocean · Waterfront · Balcony ·
From
$130/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Ocean
Waterfront
Beach
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Corner 2-bed / 2-bath Unit #926, in the Stoneybrook Golf and Country Club
6
Good
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 6
·
Hardwood Floor · Carpet · High Ceilings ·
From
$140/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Hardwood Floor
Carpet
High Ceilings
Walk In Closets
Dishwasher
Pool
Oven
In Unit Laundry
Other spaces
Kitchen
Beautiful 2 Br. Condo (225507) by Houzlet
No reviews
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
High Ceilings · Dishwasher · Pool ·
From
$169/nightProperty
Condo · 2 Beds · 2 baths
Amenities
High Ceilings
Dishwasher
Pool
Oven
Furnished
Swimming Pool
Fitness Center
Other spaces
Kitchen
New Custom Smart Home Sarasota Family Getaway
10
Excellent
·
Osprey
·
3 br
·
Sleeps 8
·
Workspace · Outdoor Space · Dishwasher ·
From
$431/nightProperty
House · 3 Beds · 3 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Garage Parking
Other spaces
Workspace, Kitchen
Paradise with a pool, pier and private beach area
10
Excellent
·
Osprey
·
5 br
·
Sleeps 12
·
On Site Laundry · Workspace · Balcony ·
From
$865/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
On Site Laundry
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Balcony, Kitchen
Forever Summer Home with King Bed | By Beach
No reviews
·
Osprey
·
2 br
·
Sleeps 6
·
Free Parking · Balcony · Dishwasher ·
From
$283/nightProperty
House · 2 Beds · 2 baths
Amenities
Free Parking
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Spacious Waterfront Retreat
9.9
Excellent
·
Osprey
·
3 br
·
Sleeps 6
·
Outdoor Space · Dishwasher · Pool ·
From
$179/nightProperty
House · 3 Beds · 3 baths
Amenities
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
Casey Key Paradise
10
Excellent
·
Osprey
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · In Unit Laundry ·
From
$2,418/nightProperty
House · 3 Beds · 4 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Garage Parking
Fitness Center
Other spaces
Kitchen
2BR/2BA 1st Floor Condo in Stoneybrook Golf & Country Club
10
Excellent
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Fitness Center · Outdoor Space · Dishwasher ·
From
$75/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Fitness Center
Dishwasher
Pool
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Showing 1 - 50 of 54 results
Updated: March 28, 2023
Learn about vacation rentals in
Osprey
Explore 54 vacation rentals near Osprey, Florida. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Osprey, you can see photos of Osprey vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Osprey vacation rentals in specific areas. Whether you’re looking for a Osprey staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Osprey is $75 per night and the highest price is $2,418 per night.
22 of the vacation rentals near Osprey are
apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation
units is $149 per night. There are
currently 11 vacation units under this
price. 26 of the vacation rentals near Osprey are houses.
The average bathroom count for a vacation house near Osprey is
2. The average price for vacation houses near Osprey is $363 per night. There are 19 vacation homes under this price. The most common
amenities for vacation rentals near Osprey are: furnished, air conditioning, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
7 available
2 bed rentals
30 available
3 bed rentals
14 available
4+ bed rentals
3 available
Getting around Osprey
Walking
3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
1/10
FYI, there are little to no public transit options within walking distance.
Points of interest in Osprey
Groceries
3/10
No grocery stores within walking distance
Shopping
3/10
Some shops within walking distance
Cafes
2/10
Few or no cafés within walking distance
Restaurants
3/10
Few or no restaurants within walking distance
Parks
7/10
Moderate amount of park space nearby
Nightlife
2/10
Few or no bars within walking distance
Vacation Rentals in Osprey, FL FAQ
How many vacation rentals in Osprey are available?
There are currently 54 vacation rentals in Osprey available. Our vacation rentals in Osprey include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Osprey?
Yes, right now there are 22 pet friendly vacation rentals in Osprey. A pet friendly vacation rental in Osprey means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Osprey with a pool?
Yes there are vacation rentals with a pool available in Osprey, FL. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Osprey with internet access?
As of March 28, 2023, there are vacation rentals with internet access available in Osprey, Florida. Check out more enjoyable destinations on Vacations by Zumper.
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