Title: Book the Best HISTORIC Hotels in Osprey in 2025 | Expedia.ca

  

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# Find Historic Hotels in Osprey, FL from CA $315

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## Check availability on Osprey Historic Hotels

Tonight

[Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Osprey Historic Hotels

![Beach](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/8aa0ab0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/ba244c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/1da0f055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/7c9280ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Sarasota

9.6/10

Exceptional

(35)

"Great place, clean, fully stocked kitchen, very convenient location. Would definitely stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nan G.

CA $113

CA $564 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Sarasota-Hotels-Extremely-Comfortableclean-VILLAS-Heated-Pool-And-Jacuzzi-SUMMER-SPECIAL-RATES.h33393742.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/bfa1f244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/3810f46f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/ea0f25fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/5d0c0eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropical, private, downtown

Central Sarasota

9.6/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie L.

CA $70

CA $353 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-Very-Tropical.h24253065.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/w1400h930x0y3-6866132b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/615f082b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/09ec13c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/4f39f7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR King/ensuite with Kitchen 5 Mins. To Beach/Downtown

Central Sarasota

10/10

Exceptional

(11)

"Great location. Easy check n check out. Cute coffee shop and restaurant below. Thank you for the hospitality!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ashley R.

CA $209

CA $320 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-1BR-Kingensuite-With-Kitchen-5-Mins-To-Beachdowntown.h19297785.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/56d6d62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/7926e0c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/9cd77b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/09b4a5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise Retreat with HEATED POOL-- Need We Say More

South Bradenton

10/10

Exceptional

(175)

"Very close to the beaches and restaurants! Nice home and owners."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brandon L.

CA $127

CA $427 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Bradenton-Hotels-Paradise-Retreat-With-HEATED-POOL-Need-We-Say-More.h24156060.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/5e0d8579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sport court](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/42c0a4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/b8cf3ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/4f7cba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants

Bradenton

9.8/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jenifer M.

CA $124

CA $415 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-Newly-Listed-Upgraded-Waterfront-Condonear-Beachesimg-Academyanna-Mariasrq.h41375487.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/a6b1997c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/cdcfe3b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/c848809a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/812fc075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Bradenton

9.8/10

Exceptional

(144)

"Great location, clean, everything we needed for a low key beach vacation!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie H.

CA $124

CA $415 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-Cozy-Condo-Free-Wifi.h23592665.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/bca94bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/efdcbaed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/ac2ea9ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, DVD player, foosball](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/4235949a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SEPT OCT NOV DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK

South Bradenton

9.8/10

Exceptional

(137)

"House and pool were great! Jackie is a great host! We really enjoyed our stay and plan to come again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brandi C.

CA $174

CA $755 total

includes taxes & fees

Nov 8 - Nov 9

[](https://www.expedia.ca/Bradenton-Hotels-APRIL-MAY-JUNE-DISCOUNTS-IMG-AMISLAND-BEACHES-KAYAK-FISHING-ON-LAKE-KIDS-PETS-OK.h30360582.Hotel-Information)

![On the beach, beach umbrellas](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973367/ae70f415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973367/315ee225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973367/b916a93d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973367/e710e657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachside Studio in Longboat Key - Silver Sands #253A Resort by RVA

Longboat Key

8.6/10

Excellent

(35)

"I really enjoyed my stay at the Silver Sands and will recommend your property"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeff H.

CA $205

CA $449 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-253a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23973367.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587942/0f2722db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587942/236574ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587942/645e7207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587942/53b2dd70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants

Bradenton

9.8/10

Exceptional

(186)

"What a lovely place to stay that is centrally located to everything. Ervin was quick to respond to questions and very accommodating. I would highly recommend staying here!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shelley F.

CA $125

CA $418 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Sarasota-Hotels-Modern-Lakefront-Condo-Lanai.h23587942.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/w1400h930x0y3-50dc3034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/57eba4a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/c73b091a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/9f33c0cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### August Ringling Room - Stay in a piece of Sarasota history - Downtown & Beaches

Central Sarasota

9.0/10

Wonderful

(15)

"Loved the atmosphere, books everywhere, coffee bar, live music, wine bar, and lack of pretentiousness."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ann P.

CA $209

CA $315 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-August-Ringling-Room-Stay-In-A-Piece-Of-Sarasota-History-Downtown-Beaches.h22127530.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&regionId=55888&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Osprey Hotel Reviews

![Golden Host Resort - Sarasota](//images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg)

### Golden Host Resort - Sarasota

10/10 Excellent

"Reception staff was very friendly."

[](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information)

![Casey Key Resorts - Mainland](//images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg)

### Casey Key Resorts - Mainland

10/10 Excellent

"Staff were very friendly & accommodating, rooms are clean. "

[](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information)

![Comfort Suites Sarasota - Siesta Key](//images.trvl-media.com/lodging/6000000/5640000/5637500/5637457/a4f997ef_y.jpg)

### Comfort Suites Sarasota - Siesta Key

10/10 Excellent

"The hotel was good and staff was great"

[](https://expedia.ca/Sarasota-Hotels-Comfort-Suites-Sarasota-Siesta-Key.h5637457.Hotel-Information)

![Spark by Hilton Sarasota Siesta Key Gateway](//images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg)

### Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"I love the bartender girl from the pool bar… so sweet"

[](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information)

![Captiva Beach Resort](//images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375_y.jpg)

### Captiva Beach Resort

10/10 Excellent

"Very good stay, clean, safe, and steps from the beach"

[](https://expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information)

![Tropical Beach Resorts](//images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg)

### Tropical Beach Resorts

10/10 Excellent

"The property is stunning, A pool with three waterfalls turf lounging. Tiki huts. The staff incredibly friendly & accommodating. Beach is in walking distance. I would come back again & again. Oh the Room perfect Tropical, clean, comfy bed. "

[](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information)

![Lido Beach Resort](//images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg)

### Lido Beach Resort

10/10 Excellent

"Clean, comfy bed and linens, outstanding view, everyone we encountered were friendly and very accommodating. Can’t wait to book another stay!"

[](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information)

![Hyatt Place Sarasota/Bradenton Airport](//images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg)

### Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"Clean room, nice sitting area, the only issue was with the bathroom door. It’s a cramped toilet/shower space making it a challenge to get out of the bathroom after your shower."

[](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information)

![Lantern Inn & Suites](//images.trvl-media.com/lodging/1000000/450000/448500/448416/4f77412a_y.jpg)

### Lantern Inn & Suites

10/10 Excellent

"I am Walking Across America for Mental Health Awareness & Recovery, over 9,100 miles! I have been in the Manatee County, Florida area for a little while, as I’ve been covered some extra distance and meeting people. This hotel has been freshly renovated, and they have amazing grades as they are trying to let people know where to go around here, especially if you want a really nice room and save a few bucks compared to everything else in the area! The people have been very friendly, And the rooms are definitely nice. Pretty good size TV as well. Definitely enjoyed it!"

[](https://expedia.ca/Sarasota-Hotels-Lantern-Inn-Suites.h448416.Hotel-Information)

## 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 65 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.

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