Historic Hotels & Resorts in Osprey from AU$278

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Best 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
9.6 out of 10, Exceptional, (35)
"Great place, clean, fully stocked kitchen, very convenient location. Would definitely stay again."
United States
Nan G.
The price is AU$637
includes taxes & fees
24 Oct - 25 Oct
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Exterior
Tropical, private, downtown
Tropical, private, downtown
9.6 out of 10, Exceptional, (78)
"Place was perfect for our short stay! Great location, roomy enough for two adults and two small pups. Very cute inside, would stay here again! "
United States
Stephanie L.
The price is AU$514
includes taxes & fees
24 Oct - 25 Oct
Tropical, private, downtown
Beach
Paradise Retreat with HEATED POOL-- Need We Say More
Paradise Retreat with HEATED POOL-- Need We Say More
10.0 out of 10, Exceptional, (175)
"Very close to the beaches and restaurants! Nice home and owners."
United States
Brandon L.
The price is AU$507
includes taxes & fees
24 Oct - 25 Oct
Paradise Retreat with HEATED POOL-- Need We Say More
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
9.2 out of 10, Wonderful, (14)
"Cute place .. excellent food"
United States
Cindy M.
The price is AU$278
includes taxes & fees
26 Oct - 27 Oct
Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything
Outdoor pool, a heated pool
SEPT OCT NOV DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK
SEPT OCT NOV DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK
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 AU$790
includes taxes & fees
26 Oct - 27 Oct
SEPT OCT NOV DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK
A heated pool
Relaxing 2BR Retreat-Silver Sands Resort
Relaxing 2BR Retreat-Silver Sands Resort
9.6 out of 10, Exceptional, (25)
"Our stay on the Gulf was everything we anticipated that it would be."
United States
Christine J.
The price is AU$653
includes taxes & fees
26 Oct - 27 Oct
Relaxing 2BR Retreat-Silver Sands Resort
A heated pool
Silver Sands #245A Resort by RVA
Silver Sands #245A Resort by RVA
8.8 out of 10, Excellent, (59)
"They are still recovering a bit from the storms past but longboat is a great local get away and this little place was very quiet and nice."
United States
Kimberly P.
The price is AU$446
includes taxes & fees
26 Oct - 27 Oct
Silver Sands #245A Resort by RVA
Beach nearby, beach umbrellas
Couple’s Beach Escape - The Beach Club at Siesta Key #106C by RVA
Couple’s Beach Escape - The Beach Club at Siesta Key #106C by RVA
9.4 out of 10, Exceptional, (101)
"Rental was clean and well taken care of. Love how close we were to the beach! Would stay here again!"
United States
Mandi R.
The price is AU$474
includes taxes & fees
27 Oct - 28 Oct
Couple’s Beach Escape - The Beach Club at Siesta Key #106C by RVA
A heated pool
Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA
Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA
8.8 out of 10, Excellent, (42)
"Enjoyed our stay"
United States
Susan C.
The price is AU$446
includes taxes & fees
26 Oct - 27 Oct
Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA
Beach
Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
9.8 out of 10, Exceptional, (111)
"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 AU$464
includes taxes & fees
27 Oct - 28 Oct
Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"We didn't spend much time there except to sleep."
William 1-night trip
Posted 4 days ago
Spark by Hilton Sarasota Siesta Key Gateway

Frequently asked questions

What should a history enthusiast expect from a trip to Osprey?
Significant historical sites in Osprey are probably a big part of your travel plans. 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 are located in Osprey?
Osprey is home to 65 hotels bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical places and other sights to visit in Osprey?
Osprey is notable for landmarks like Historic Spanish Point. The natural setting is picturesque, namely the beaches, and places to see include: 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?
When you choose a historic hotel, you'll stay someplace that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be identified as a historic hotel as long as it's of special interest. Traditional architecture and period features are typically preserved in the communal spaces and guestrooms of historic hotels in Osprey, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is a term often used in the U.S. but overall the terms are quite similar. The building and architecture of a historic hotel tends to be what's most significant. For a heritage hotel, it's often the cultural value and how it shaped the community.
Do historic hotels in Osprey have modern facilities?
Hotel interiors feature the modern conveniences and safety features you've come to expect, 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 popular amenities found in a hotel will also be available in a historic hotel. When you choose a historic hotel in Osprey, don't worry that you'll find a place that's uncomfortable for guests or simply rundown.