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Check availability on Osprey Historic Hotels

Our top choices for Osprey historic hotels

Property grounds

BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Sarasota
9.6 out of 10, Exceptional, (52 reviews)
"Beautiful apartment located near the beach and state parks"
United States
Eliot f.
The price is AED 397
AED 1,673 total
includes taxes & fees
1 Jul - 2 Jul
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Beach nearby, sun loungers, beach towels

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!
South Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Beautiful pool, nice kitchen, and close to Anna Marie Island."
United States
Gary B.
The price is AED 496
AED 2,009 total
includes taxes & fees
30 Jun - 1 Jul
IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!
Beach nearby, beach towels

Lakeview Corner Condo · Two Pools · Near IMG · Anna Maria Island · Restaurants

Lakeview Corner Condo · Two Pools · Near IMG · Anna Maria Island · Restaurants
Bradenton
9.8 out of 10, Exceptional, (121 reviews)
"We loved the property, large pool & access to activities. "
United States
Mary Beth M.
The price is AED 406
AED 1,133 total
includes taxes & fees
21 Jun - 22 Jun
Lakeview Corner Condo · Two Pools · Near IMG · Anna Maria Island · Restaurants
Sun loungers, beach towels

Cozy Corner Condo · Two Pools & Hot Tubs · IMG · Anna Maria Island · Restaurants

Cozy Corner Condo · Two Pools & Hot Tubs · IMG · Anna Maria Island · Restaurants
Bradenton
9.8 out of 10, Exceptional, (159 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
The price is AED 393
AED 1,119 total
includes taxes & fees
21 Jun - 22 Jun
Cozy Corner Condo · Two Pools & Hot Tubs · IMG · Anna Maria Island · Restaurants
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, (190 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is AED 555
AED 1,393 total
includes taxes & fees
29 Jun - 30 Jun
Paradise Retreat with HEATED POOL-- Need We Say More
Marina

Very tropical, private and peaceful, short walk to everything happening downtown

Very tropical, private and peaceful, short walk to everything happening downtown
Central Sarasota
9.6 out of 10, Exceptional, (74 reviews)
"We loved the location! The neighborhood is charming and walkable to downtown Sarasota. We loved the secluded garden that was so inviting. Unfortunately, weather didn’t permit us to take advantage of it. We hope to return! "
United States
Christine B.
The price is AED 400
AED 1,315 total
includes taxes & fees
22 Jun - 23 Jun
Very tropical, private and peaceful, short walk to everything happening downtown
On the beach, 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, (63 reviews)
"We had the most wonderful stay despite the cold temps for most it! The staff at our location are above and beyond to make sure you have everything you need! Highly recommend!"
United States
Sahra S.
The price is AED 573
AED 1,237 total
includes taxes & fees
24 Jun - 25 Jun
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
On the beach, beach umbrellas

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (79 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is AED 536
AED 1,186 total
includes taxes & fees
23 Jun - 24 Jun
Affordable Beach Studio – Silver Sands #257A by RVA
On the beach, beach umbrellas

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.2 out of 10, Wonderful, (104 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
The price is AED 702
AED 1,399 total
includes taxes & fees
21 Jun - 22 Jun
Gulf Front Escape – Silver Sands #252 by RVA
Exterior

Tropical, private, downtown

Tropical, private, downtown
Central Sarasota
9.6 out of 10, Exceptional, (91 reviews)
"Super cute place in a great location!"
United States
Lisa A.
The price is AED 419
AED 970 total
includes taxes & fees
22 Jun - 23 Jun
Tropical, private, downtown
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.
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Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"This was a lot better stay from last time I stayed. Had hot water, lights worked and didn’t have to have my room changed. As always the staff were super nice."
Holly 2-night trip
Posted 1 hour ago
Casey Key Resorts - Mainland

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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 56 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.