Vacation Rentals in Osprey, FL
PRICE PER NIGHT
ACCOMMODATION TYPES
Top-Rated Vacation Rentals in Osprey, FL
Book a vacation rental in Osprey that has the highest visitor rating. Here are 6 of the best vacation rentals in Osprey.
Price drop
Casey Key Paradise
10
Excellent
·
Osprey
·
3 br
·
Sleeps 6
·
Air Conditioning · Garage Parking · Dishwasher ·
From
$2,345/nightProperty
House · 3 Beds · 4 baths
Amenities
Air Conditioning
Garage Parking
Dishwasher
Fitness Center
Oven
Beach
Furnished
Wifi
Other spaces
Kitchen
14 Minutes from Siesta Key Beaches!
10
Excellent
·
Sarabay Acres
·
3 br
·
Sleeps 6
·
In Unit Laundry · Swimming Pool · Beach ·
From
$172/nightProperty
Condo · 3 Beds · 2 baths
Amenities
In Unit Laundry
Swimming Pool
Beach
Air Conditioning
Wifi
Furnished
Pool
Fitness Center
Other spaces
Kitchen
Pool, Hot tub, Close to Beaches, Shopping, More!
10
Excellent
·
Osprey
·
3 br
·
Sleeps 8
·
Furnished · Hot Tub · Pool ·
From
$237/nightProperty
House · 3 Beds · 2 baths
Amenities
Furnished
Hot Tub
Pool
Beach
Oven
Residents Lounge
Air Conditioning
Dishwasher
Other spaces
Kitchen
Price drop
Stunning 2 Bedroom Condo---- 5 Minutes from the Beach!
10
Excellent
·
Osprey
·
2 br
·
Sleeps 4
·
Pool · Wifi · Swimming Pool ·
From
$204/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Pool
Wifi
Swimming Pool
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Price drop
The Shoreland Hideaway 4BR/ 2BA with pool, 15 mins from Siesta Key
10
Excellent
·
Osprey
·
4 br
·
Sleeps 13
·
Dishwasher · Hot Tub · Wifi ·
From
$326/nightProperty
House · 4 Beds · 2 baths
Amenities
Dishwasher
Hot Tub
Wifi
Fitness Center
Residents Lounge
Furnished
Oven
Pool
Other spaces
Kitchen
Price drop
Paradise with a pool, pier and private beach area
10
Excellent
·
Osprey
·
5 br
·
Sleeps 12
·
Pool · Wheelchair Accessible · Garage Parking ·
From
$576/nightProperty
Apartment · 5 Beds · 4 baths
Amenities
Pool
Wheelchair Accessible
Garage Parking
Oven
In Unit Laundry
Waterfront
Wifi
Swimming Pool
Other spaces
Kitchen, Balcony, Workspace
Our Recommended Vacation Rentals in Osprey, FL
We analyzed vacation rentals in Osprey from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Osprey to help you find a deal for your next trip.
Charming Florida Beach Home w/ King Bed, Patio
No rating
·
Sarabay Acres
·
2 br
·
Sleeps 6
·
Outdoor Space · Air Conditioning · Workspace ·
From
$146/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Air Conditioning
Business Center
Oven
Tv
Microwave
In Unit Laundry
Free Parking
Central Heat
Other spaces
Workspace, Kitchen, Garden
Relaxing 2BR Florida Home Close to Beach
No rating
·
Sarabay Acres
·
2 br
·
Sleeps 6
·
Central Heat · Air Conditioning · Outdoor Space ·
From
$140/nightProperty
House · 2 Beds · 2 baths
Amenities
Central Heat
Air Conditioning
In Unit Laundry
Microwave
Free Parking
Business Center
Dishwasher
Tv
Other spaces
Kitchen
Price drop
2 Bed, 2 Bath Condo in Golf Community $2050-$4800/month - 9300 Clubside"
No rating
·
Stoneybrook Golf and Country Club
·
2 br
·
Cable · Carpet · Microwave ·
From
$83/nightMin stay: 30 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Cable
Carpet
Microwave
Furnished
In Unit Laundry
Air Conditioning
Swimming Pool
Dishwasher
Budget-Friendly Vacation Rentals in Osprey, FL
Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Osprey starting at $65. Use the price filter at the top of the page to search for more specific prices.
Stoneybrook Golf Community. 1st floor. 2bed2bath.
No rating
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Furnished · Workspace · Kitchen ·
From
$65/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Furnished
Dishwasher
Pool
Air Conditioning
Assigned Parking
Walk In Closets
On Site Laundry
Residents Lounge
Other spaces
Workspace, Kitchen
Available in 2024-Quiet spacious condo in Osprey
No rating
·
Osprey
·
2 br
·
Microwave · Fitness Center · On Site Laundry ·
From
$70/nightMin stay: 30 nights
Property
Condo · 2 Beds · 2 baths
Amenities
Microwave
Fitness Center
On Site Laundry
Dishwasher
In Unit Laundry
Swimming Pool
Assigned Parking
High Ceilings
Price drop
2BR/2BA 1st Floor Condo in Stoneybrook Golf & Country Club
10
Excellent
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Residents Lounge · Pool · Elevator ·
From
$77/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Residents Lounge
Pool
Elevator
Fitness Center
Furnished
Oven
Hot Tub
Air Conditioning
Other spaces
Kitchen
Price drop
Stoneybrook Golf & CC
10
Excellent
·
Stoneybrook Golf and Country Club
·
2 br
·
Sleeps 4
·
Air Conditioning · Hot Tub · Furnished ·
From
$85/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Air Conditioning
Hot Tub
Furnished
Dishwasher
Swimming Pool
Wifi
Beach
Pool
Other spaces
Kitchen
Paradise Home away from Home: Golf, Swimming, Tennis, & lots of Fun in the Sun!
10
Excellent
·
Stoneybrook Golf and Country Club
·
3 br
·
Sleeps 6
·
Furnished · Outdoor Space · Swimming Pool ·
From
$85/nightProperty
Condo · 3 Beds · 2 baths
Amenities
Furnished
Swimming Pool
Pool
In Unit Laundry
Oven
Wifi
Air Conditioning
Dishwasher
Other spaces
Kitchen
Family-Friendly Vacation Rentals in Osprey, FL
Heading to Osprey for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
Private guest house with king bed & loft. Deck with hot tub and putting green
No rating
·
Osprey
·
1 br
·
Sleeps 6
·
Furnished · Workspace · Outdoor Space ·
From
$226/nightProperty
House · 1 Bed · 1 bath
Amenities
Furnished
Air Conditioning
Hot Tub
Wifi
In Unit Laundry
Other spaces
Workspace, Kitchen
Pine Run Dog Friendly Condo! Close to beaches!
10
Excellent
·
Osprey
·
1 br
·
Sleeps 3
·
In Unit Laundry · On Site Laundry · Balcony ·
From
$90/nightProperty
Condo · 1 Bed · 1 bath
Amenities
In Unit Laundry
On Site Laundry
Pool
Dishwasher
Swimming Pool
Air Conditioning
Oven
Fitness Center
Other spaces
Balcony, Kitchen
Sarasota Stoneybrook Golf Condo near Siesta Key
10
Excellent
·
Stoneybrook Golf and Country Club
·
Studio
·
Sleeps 6
·
Elevator · Residents Lounge · Balcony ·
From
$140/nightProperty
Condo · Studio · 2 baths
Amenities
Elevator
Residents Lounge
Furnished
Wifi
In Unit Laundry
Dishwasher
Air Conditioning
Pool
Other spaces
Balcony, Kitchen
Expand your search criteria to see more vacation rentals near Osprey.
Updated: October 4, 2023
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