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

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# Find Historic Hotels in Osprey, FL from CA $375

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## Check availability on Osprey Historic Hotels

Tonight

[Jan 4 - Jan 5](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-04&endDate=2026-01-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[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)

Next 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)

In two weeks

[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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/3520b4e1.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)

### 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)

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/w1433h1080x243y0-4e41ebca.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)

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

![Exterior](https://images.trvl-media.com/lodging/35000000/34090000/34084900/34084885/2ccd24d9.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)

![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)

### 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/42000000/41380000/41375500/41375487/5e0d8579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/7b0de6bf.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)

![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)

### 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

(114)

"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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/e5394b08.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)

### 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)

![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)

![Exterior](https://images.trvl-media.com/lodging/37000000/36360000/36358600/36358504/3c43f7cf.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 $275

CA $375 total

includes taxes & fees

Jan 5 - Jan 6

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

![Exterior](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/a0f04c5e.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 $198

CA $439 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)

![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/25000000/24260000/24253100/24253065/9281a2a0.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)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/d9da119b.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 5 - Jan 6

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

![A heated pool](https://images.trvl-media.com/lodging/24000000/23100000/23099900/23099822/e988cae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23100000/23099900/23099822/6b6b32c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23100000/23099900/23099822/ed9ecadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23100000/23099900/23099822/c3811966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal Comfort – Silver Sands Resort #233 by RVA

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-233-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23099822.Hotel-Information)

Longboat Key

8.8/10

Excellent

(31)

"We spent 3 beautiful days with you. The room was clean and comfortable. Your grounds and pool were well maintained. Very pleasant stay and I will definitely be back. "

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

Martha R.

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-233-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23099822.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/24000000/23600000/23592100/23592089/1a7a9764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23600000/23592100/23592089/35bf8d6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23600000/23592100/23592089/9372a33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23600000/23592100/23592089/afb2af29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Beach Oasis – Silver Sands #258, Longboat Key by RVA

[](https://www.expedia.ca/Longboat-Key-Hotels-Silver-Sands-258-Resort-By-RVA.h23592089.Hotel-Information)

Longboat Key

8.8/10

Excellent

(24)

"Great location. We loved that it was an easy drive to lots of parks an other attractions. Great beach walks."

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

Deb W.

CA $289

CA $540 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Longboat-Key-Hotels-Silver-Sands-258-Resort-By-RVA.h23592089.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=2026-01-18&endDate=2026-01-19&regionId=55888&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Osprey Hotel Reviews

![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)

![Holiday Inn Express Sarasota East - I-75 by IHG](https://images.trvl-media.com/lodging/1000000/920000/912600/912573/2da17d8e_y.jpg)

### Holiday Inn Express Sarasota East - I-75 by IHG

10/10 Excellent

"Staff were kind. Rooms looked good"

[](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Express-Sarasota-East-I-75.h912573.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)

![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

"Room was big and clean. Good amenities and great staff at the breakfast area."

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

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

### Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"The staff very friendly and helpful. The rooms were very clean and comfortable. Pool and bar was fun. Great location."

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