Title: Book the Best HISTORIC Hotels in Osprey in 2026 | Expedia.ca

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# Find Historic Hotels in Osprey, FL from CA $306

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## Check availability on Osprey Historic Hotels

Tonight

[Jan 5 - Jan 6](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-05&endDate=2026-01-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-06&endDate=2026-01-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Osprey historic hotels

![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/6fb611a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/822b1606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edfdd191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/c128477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Floridian cottage in Historic Gulf Village

[](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information)

Olde Englewood Village

9.8/10

Exceptional

(60)

"Very good, great location 👍👍"

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

James M.

CA $204

CA $428 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/0a2ca754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/w1074h1080x424y0-6802a200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/8cf16f4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/w827h548x0y12-b864f7b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Venice Island Beach walk 2 beach, Sharkey’s, legacy trail,-2 homes available

[](https://www.expedia.ca/Venice-Hotels-Venice-Island-Beach-Walk-2-Beach.h18978028.Hotel-Information)

Venice Island

9.8/10

Exceptional

(105)

"Absolutely wonderful rental home, very clean and comfortable in a fabulous location close to town and the beaches. One of my best stays in Venice and would highly recommend!"

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

Bonnie S.

CA $242

CA $618 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Venice-Hotels-Venice-Island-Beach-Walk-2-Beach.h18978028.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)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/d9da119b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/36d1ce5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/ef34879b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropical, private, downtown

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

Central Sarasota

9.4/10

Exceptional

(83)

"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 $232

CA $455 total

includes taxes & fees

Jan 6 - Jan 7

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/37000000/36360000/36358600/36358504/w1400h930x0y3-969270a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36360000/36358600/36358504/39e7f9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/37000000/36360000/36358600/36358504/311350e2.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/37000000/36360000/36358600/36358504/e6fb9ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Sarasota-Hotels-Historically-Significant-1-BR.h36358504.Hotel-Information)

Central Sarasota

9.2/10

Wonderful

(15)

"Cute place .. excellent food"

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

Cindy M.

CA $378

CA $506 total

includes taxes & fees

Jan 6 - Jan 7

[](https://www.expedia.ca/Sarasota-Hotels-Historically-Significant-1-BR.h36358504.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/35000000/34090000/34084900/34084885/38a95128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34090000/34084900/34084885/3c2fa384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, computer monitors](https://images.trvl-media.com/lodging/35000000/34090000/34084900/34084885/14bdc1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34090000/34084900/34084885/70023d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Screened, heated pool - Sarasota extended stay home near Siesta Key Beach

[](https://www.expedia.ca/Sarasota-Hotels-Screened.h34084885.Hotel-Information)

Gulf Gate Estates

10/10

Exceptional

(53)

"Such a pretty home, located in a lovely, quiet neighborhood, close to great beaches, shopping and dining. Beautiful pool with covered lanai - great for enjoying your morning coffee and all that sunshine! House is beautifully equipped and great communication with the owner! Love this home and area!!"

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

Jim B.

CA $288

CA $751 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Sarasota-Hotels-Screened.h34084885.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/5ba3c4a8.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)

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

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

Central Sarasota

9.0/10

Wonderful

(15)

"Great location to Ringling attractions. Two restaurants on property, both excellent"

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

Reagan S.

CA $206

CA $306 total

includes taxes & fees

Jan 6 - Jan 7

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

![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)

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

### Elegant Waterfront Condo: Two Pools\~Private Lanai\~WiFi! Near IMG\~AMI\~Restaurants

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

Bradenton

9.8/10

Exceptional

(115)

"Enjoyed our stay, we will return for future fun in AMI"

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

Karen J.

CA $146

CA $439 total

includes taxes & fees

Jan 7 - Jan 8

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/3b1f5330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/f9fd40d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, DVD player, foosball](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/5a065293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/2f31e4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### IMG Lake & Beach Home HOT Pool White Sand Beaches Kid&Pets OK Great Location!

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

South Bradenton

9.8/10

Exceptional

(137)

"everything was great had everything we need and more, would book again for sure."

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

Kyrese S.

CA $205

CA $774 total

includes taxes & fees

Jan 12 - Jan 13

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

![A heated pool](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/af73f449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/4150dd9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/14c34a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/c3fed7e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Serenity – Unit 234 by RVA

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-234-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23058218.Hotel-Information)

Longboat Key

9.4/10

Exceptional

(30)

"Love this place and staff. Will book again. Everything is so easy!"

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

Emily

CA $199

CA $437 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-234-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23058218.Hotel-Information)

![TV, DVD player, stereo, offices](https://images.trvl-media.com/lodging/29000000/28780000/28770500/28770443/9189c9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/29000000/28780000/28770500/28770443/2c11a31c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/29000000/28780000/28770500/28770443/69d57d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/29000000/28780000/28770500/28770443/f043cdd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gulf Views – Silver Sands #259, Longboat Key by RVA

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-250-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h28770443.Hotel-Information)

Longboat Key

9.0/10

Wonderful

(74)

"Beautiful beach, great views from the balcony, we had a great stay."

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

Meghan P.

CA $267

CA $526 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-250-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h28770443.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=2026-01-19&endDate=2026-01-20&regionId=55888&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Osprey Hotel Reviews

![Hibiscus Suites - Gateway to Siesta Key](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07_y.jpg)

### Hibiscus Suites - Gateway to Siesta Key

10/10 Excellent

"Everything work and very clean"

[](https://expedia.ca/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information)

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

### Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent

"Excelente elección "

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

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

### Captiva Beach Resort

10/10 Excellent

"This hotel was great! We had a two bedroom suite for a very reasonable rate. Well stocked kitchen, clean, close to the beach, easy parking, nice front desk staff. I would recommend this hotel very much. "

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

![Quality Inn Sarasota North Near Lido Key Beach](https://images.trvl-media.com/lodging/1000000/30000/23000/22938/d0d73f0b_y.jpg)

### Quality Inn Sarasota North Near Lido Key Beach

10/10 Excellent

"Great"

[](https://expedia.ca/Sarasota-Hotels-Quality-Inn-Sarasota-North-Near-Lido-Key-Beach.h22938.Hotel-Information)

![DoubleTree by Hilton Sarasota Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg)

### DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"Beautiful hotel. Everything is new and modern."

[](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information)

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

### Lido Beach Resort

10/10 Excellent

"Excellent rooms. Clean and spacious"

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

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

### Tropical Beach Resorts

10/10 Excellent

"The staff were very friendly! The room was clean and very comfortable. We enjoyed the heated pool. Can't beat sunset at the beach. This location is walkable to several restaurants. And it's just a short drive to the Village. Highly recommend!"

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

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

### Golden Host Resort - Sarasota

10/10 Excellent

"The staff was amazing the only thing my stay was for a week and we asked for the bed to be changed every day it it only was done for the first 2 days "

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

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

### Casey Key Resorts - Mainland

10/10 Excellent

"Staff and cleanliness "

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

## Frequently asked questions

### What should I expect on my historical trip to Osprey?

### How many historically relevant hotels will I find in Osprey?

### What are the top historical sites and other places to visit in Osprey?

### What is a historic hotel like in Osprey?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Osprey have modern facilities?

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