Find Historic Hotels in Osprey, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Osprey Historic Hotels

Tonight
5 May - 6 May
Tomorrow
6 May - 7 May
This weekend
8 May - 10 May
Next weekend
15 May - 17 May

Our top choices for Osprey historic hotels

Beach nearby, beach towels

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (120 reviews)
"Perfect spot and host "
United States
Dee B.
The price is AED 375
AED 1,056 total
includes taxes & fees
7 May - 8 May
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Sun loungers, beach towels

Beautiful 2BR Condo · IMG 5 Mins · Anna Maria Island 15 Mins · Pools & Hot Tubs

Beautiful 2BR Condo · IMG 5 Mins · Anna Maria Island 15 Mins · Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
The price is AED 390
AED 1,070 total
includes taxes & fees
6 May - 7 May
Beautiful 2BR Condo · IMG 5 Mins · Anna Maria Island 15 Mins · Pools & Hot Tubs
Beach

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (183 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is AED 549
AED 1,386 total
includes taxes & fees
6 May - 7 May
Paradise Retreat with HEATED POOL-- Need We Say More
Sun loungers

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Stayed at the same place before, lovely accommodation and location, and the host very welcoming and professional."
United States
John S.
The price is AED 459
AED 1,285 total
includes taxes & fees
11 May - 12 May
*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Exterior

Tropical, private, downtown

Tropical, private, downtown
Central Sarasota
9.4 out of 10, Exceptional, (88 reviews)
"Wonderful host in a great location!"
United States
Milissa D.
The price is AED 411
AED 958 total
includes taxes & fees
6 May - 7 May
Tropical, private, downtown
Beach umbrellas

Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Would def stay here again!"
United States
Tammie and David
The price is AED 573
AED 1,226 total
includes taxes & fees
13 May - 14 May
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Beach umbrellas

Gulfside Resort – Silver Sands #241A by RVA

Gulfside Resort – Silver Sands #241A by RVA
Longboat Key
8.4 out of 10, Very Good, (49 reviews)
"We enjoyed this fun spot with private beach, pool, and more!"
United States
Willow C.
The price is AED 591
AED 1,252 total
includes taxes & fees
13 May - 14 May
Gulfside Resort – Silver Sands #241A by RVA
Beach umbrellas

Silver Sands #245A Resort by RVA

Silver Sands #245A Resort by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Location and facilities wer excellent. "
United States
donald m.
The price is AED 566
AED 1,218 total
includes taxes & fees
6 May - 7 May
Silver Sands #245A Resort by RVA
Beach umbrellas

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (94 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is AED 672
AED 1,371 total
includes taxes & fees
11 May - 12 May
1BR Beach Getaway – Silver Sands #254 by RVA
Beach umbrellas

Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
Longboat Key
8.8 out of 10, Excellent, (42 reviews)
"Enjoyed our stay"
United States
Susan C.
The price is AED 599
AED 1,272 total
includes taxes & fees
11 May - 12 May
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"Overall great stay...from breakfast in the am to the pool bar in the late afternoon...staff very friendly and accommodating. We definitely will be back again."
Lisa 3-night trip
Posted 3 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

Explore a world of travel with Expedia

Frequently asked questions

What should I expect on my historical trip to Osprey?
The historical places in Osprey are probably at the top of your sightseeing list. While you're in town, you can check out the popular beaches and lively bars. You can also relish a trip to the top-notch restaurants.
How many historically relevant hotels will I find in Osprey?
Osprey is home to 57 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the top historical sites and other places to visit in Osprey?
Osprey is notable for landmarks like Historic Spanish Point. The natural setting is picturesque, namely the stunning beaches, and these places to see: Jim Neville Marine Preserve, Turtle Beach, and Nokomis Beach. Additionally, in the area you'll find Siesta Key Beach and Lido Beach.
What is a historic hotel like in Osprey?
Guests who book a historic hotel can stay someplace that has an officially recognized historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the guestrooms or communal spaces of such hotels in Osprey, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and building of a historic hotel tends to be the most important aspect. For a heritage hotel, it's often the cultural value as well as how it inspired the community.
Do historic hotels in Osprey have modern facilities?
Hotels have the safety features and modern conveniences you expect to find, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found at a contemporary hotel will also be available in a historic hotel. When you choose a historic hotel in Osprey, don't worry that you'll find yourself staying at a place that's uncomfortable for guests or simply rundown.