Photo by Rick Tuers

Find Historic Hotels in Osprey, FL

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Top Osprey Historic Hotels

Beach
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

Sarasota
9.6 out of 10, Exceptional, (35)
"Looking forward to staying there again."
United States
aimen s.
The price is AED 588
AED 1,862 total
includes taxes & fees
4 Dec - 5 Dec
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Property grounds
Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village

Olde Englewood Village
9.8 out of 10, Exceptional, (60)
"Had a nice stay. Clean and well equipped."
United States
Debi D.
The price is AED 364
AED 918 total
includes taxes & fees
18 Nov - 19 Nov
Old Floridian cottage in Historic Gulf Village
Outdoor pool, a heated pool
NOV DEC DISCOUNTS IMG AMIsland WHITE BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK

NOV DEC DISCOUNTS IMG AMIsland WHITE BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK

South Bradenton
9.8 out of 10, Exceptional, (137)
"House and pool were great! Jackie is a great host! We really enjoyed our stay and plan to come again!"
United States
Brandi C.
The price is AED 327
AED 1,813 total
includes taxes & fees
18 Nov - 19 Nov
NOV DEC DISCOUNTS IMG AMIsland WHITE BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK
Beach nearby, sun loungers, beach towels
Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything

Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything

Central Sarasota
9.2 out of 10, Wonderful, (15)
"This room was perfect for our needs. We wanted to be within walking distance to downtown, but not pay a fortune. This was the most economical choice. It had everything we needed with a little bit of rustic charm. "
United States
Jenelle
The price is AED 459
AED 655 total
includes taxes & fees
18 Nov - 19 Nov
Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything
Beach
Superb Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Superb Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Bradenton
9.8 out of 10, Exceptional, (113)
"I stayed 1 night with 2 of my friends and honestlyEverything was amazing, place was super clean, the host was super quick to answer my questions and I would for sure booked again."
United States
Jenifer M.
The price is AED 406
AED 1,182 total
includes taxes & fees
18 Nov - 19 Nov
Superb Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
Beach
Beautiful 2BR Condo! Heated Pools~WiFi. By IMG Academy~Beaches~AMI~Restaurants.

Beautiful 2BR Condo! Heated Pools~WiFi. By IMG Academy~Beaches~AMI~Restaurants.

Bradenton
9.8 out of 10, Exceptional, (147)
"The location is great with stores very close, very close to IMG academy and for beaches.It had everything we needed for a short stay. There could be some improvements made but for the length of time we stayed it was okay. "
United States
Salisha H.
The price is AED 406
AED 1,182 total
includes taxes & fees
18 Nov - 19 Nov
Beautiful 2BR Condo! Heated Pools~WiFi. By IMG Academy~Beaches~AMI~Restaurants.
On the beach, 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, (47)
"Checkin was very easy. Studio was spotless. Right on the beach and close proximity to restaurants."
United States
Susan D.
Gulfside Resort – Silver Sands #241A by RVA
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, (178)
"Very close to the beaches and restaurants! Nice home and owners."
United States
Brandon L.
The price is AED 423
AED 1,226 total
includes taxes & fees
18 Nov - 19 Nov
Paradise Retreat with HEATED POOL-- Need We Say More
On the beach, beach umbrellas
Silver Sands #244 – 1BR/1BA Resort on Longboat Key, Sleeps 4

Silver Sands #244 – 1BR/1BA Resort on Longboat Key, Sleeps 4

4.0 star property
Longboat Key
8.8 out of 10, Excellent, (14)
"Very clean, accommodating, comfortable for two. Nice small lanai porch for morning coffee or happy hour. Easy access to beautiful beach. First couple of days were very quiet, then a family with rather boisterous kids dominated the pool area and it got noisy...would likely have said something if we weren't on our last evening. Thought that this season would have been clear of this, but evidently this family thought it a good idea to take kids out of school for a vacation. That's the risk you...
United States
Gary S.
Silver Sands #244 – 1BR/1BA Resort on Longboat Key, Sleeps 4
A heated pool
Silver Sands #245 Resort by RVA

Silver Sands #245 Resort by RVA

Longboat Key
9.4 out of 10, Exceptional, (34)
"Nice condo"
United States
Barbara C.
The price is AED 834
AED 1,586 total
includes taxes & fees
18 Nov - 19 Nov
Silver Sands #245 Resort 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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Spotless room, excellent staff, perfect location. "
William 2-night trip
Posted 1 day ago
Tropical Beach Resorts

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 top-notch restaurants. You can also relish a trip to the lively bars.
How many historically relevant hotels will I find in Osprey?
Osprey is home to 66 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: Turtle Beach, Nokomis Beach, and Jim Neville Marine Preserve. 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.