Bed and Breakfast, Guest Houses & Inns in Osprey, FL

Compare 11,558 available beachfront holiday vacation home properties, starts from $25

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Find the best vacation rental

ACCOMMODATION TYPES

Bed and Breakfast, Guest Houses & Inns: Top Deals

Turtle Beach Resort
Turtle Beach Resort
Turtle Beach Resort
Turtle Beach Resort
Turtle Beach Resort
Turtle Beach Resort
4.2 (77 reviews)
Turtle Beach Resort
Resort
$295 /night
View deal
Gulf Shores Beach Resort
Gulf Shores Beach Resort
Gulf Shores Beach Resort
Gulf Shores Beach Resort
Gulf Shores Beach Resort
Gulf Shores Beach Resort
Gulf Shores Beach Resort
4.1 (173 reviews)
Gulf Shores Beach Resort
Resort
$132 /night
View deal
Sunshine Inn & Suites Venice, Florida
Sunshine Inn & Suites Venice, Florida
Sunshine Inn & Suites Venice, Florida
Sunshine Inn & Suites Venice, Florida
Sunshine Inn & Suites Venice, Florida
Sunshine Inn & Suites Venice, Florida
Sunshine Inn & Suites Venice, Florida
4.1 (208 reviews)
Sunshine Inn & Suites Venice, Florida
Hotel
$55 /night
View deal
The Inn at Turtle Beach (Adults Only)
The Inn at Turtle Beach (Adults Only)
The Inn at Turtle Beach (Adults Only)
The Inn at Turtle Beach (Adults Only)
The Inn at Turtle Beach (Adults Only)
The Inn at Turtle Beach (Adults Only)
The Inn at Turtle Beach (Adults Only)
4.3 (85 reviews)
The Inn at Turtle Beach (Adults Only)
Hotel
$283 /night
View deal
LUX VILLAs on beautiful Palmer Ranch
LUX VILLAs on beautiful Palmer Ranch
LUX VILLAs on beautiful Palmer Ranch
LUX VILLAs on beautiful Palmer Ranch
LUX VILLAs on beautiful Palmer Ranch
LUX VILLAs on beautiful Palmer Ranch
LUX VILLAs on beautiful Palmer Ranch
4.6 (4 reviews)
LUX VILLAs on beautiful Palmer Ranch
Hotel
$128 /night
View deal
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
4.6 (69 reviews)
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
Condo · 5 Guests · 2 Bedrooms
$155 /night*
View deal
Escape Casey Key Hotel & Marina - Overnight Room 5A
Escape Casey Key Hotel & Marina - Overnight Room 5A
Escape Casey Key Hotel & Marina - Overnight Room 5A
Escape Casey Key Hotel & Marina - Overnight Room 5A
Escape Casey Key Hotel & Marina - Overnight Room 5A
Escape Casey Key Hotel & Marina - Overnight Room 5A
Escape Casey Key Hotel & Marina - Overnight Room 5A
Escape Casey Key Hotel & Marina - Overnight Room 5A
4.5 (2 reviews)
Escape Casey Key Hotel & Marina - Overnight Room 5A
Hotel · 2 Guests · 1 Bedroom
$167 /night*
View deal
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
4.5 (15 reviews)
1/1 Bed & Bath Lux Condos
Hotel
$68 /night
View deal
Home2 Suites By Hilton Nokomis
Home2 Suites By Hilton Nokomis
Home2 Suites By Hilton Nokomis
Home2 Suites By Hilton Nokomis
Home2 Suites By Hilton Nokomis
Home2 Suites By Hilton Nokomis
Home2 Suites By Hilton Nokomis
4.5 (200 reviews)
Home2 Suites By Hilton Nokomis
Hotel
$119 /night
View deal
Search all

Similar Inspirational Vacation Rental Destinations

Which Price Range Is Considered As A Good Deal in Osprey, FL Area?
Vacation Condo & House Rental Price Information in Osprey, FL
+
The graph shows the percentages of vacation homes in each price bucket. Osprey has the largest percentage (30.98%) of homes in $100 - $150 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
How Many Accommodations Are Pets Allowed in Osprey, FL?
Percentage of Pet Friendly Rental Properties in Osprey, FL
+
21.23% of vacation homes in Osprey are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Where Should We Visit in Osprey, FL Area?
Suggested Destinations To Visit in Osprey, FL
+
Which Airports Should I Choose To Get To Osprey, FL?
Top Airports in Osprey, FL
+
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers