Title: Osprey Chalets from CA $764 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Osprey chalets

![Property grounds](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/ab65f2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/dddbac26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/107e4072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/43e30509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-Private-Deck-Ocean-View-Siesta-Key-Village-Beach-Walkable.h102825157.Hotel-Information)

Siesta Key Village

9.6/10

Exceptional

(8 reviews)

"Great location to beach, food and entertainment. All within walking distance. Unit was like home aeay from home."

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

Linda

CA $675

CA $860 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-Private-Deck-Ocean-View-Siesta-Key-Village-Beach-Walkable.h102825157.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/437a5498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/05b64e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/b4f464c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/093d2125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Private-Deck-Condo.h102825143.Hotel-Information)

Siesta Key Village

9.4/10

Exceptional

(6 reviews)

"All the beach items were available for use , the room was clean , the staff was amazing, definitely will stay again . "

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

Angie

CA $1,125

CA $1,432 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Private-Deck-Condo.h102825143.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/58a17c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/ae608647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/62480ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/0d39daa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

[](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Chalet-Deck-Siesta-Key-Village-And-Beach-Walkable.h103064024.Hotel-Information)

Siesta Key Village

10/10

Exceptional

(6 reviews)

"We had a great time at Siesta key and this house was fantastic! Super easy check in/out, very clean, loves the beach chairs and umbrella - great touch!"

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

Amy L.

CA $1,350

CA $1,716 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Chalet-Deck-Siesta-Key-Village-And-Beach-Walkable.h103064024.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/0bafc1eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/1d9838e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/c1f504ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/8a02dc58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Suite-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825161.Hotel-Information)

Siesta Key Village

6.0/10

(1 review)

"Price point was really high for what you get. Small Great location! no ocean view Great communication uncomfortable bed fridge froze some of produce trees overgrown all over electrical wires within inches of the balcony very dangerous unsecure wifi unless reached out to "

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

Jason B.

CA $600

CA $764 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Suite-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825161.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/w1276h854x4y0-631b5ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/b95c27ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/f9ae06d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/8a17245f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.Hotel-Information)

Siesta Key Village

9.6/10

Exceptional

(5 reviews)

"Owner provided all the beach items and the place was clean and well kept."

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

John P.

CA $1,348

CA $1,715 total

includes taxes & fees

Mar 13 - Mar 14

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.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=2026-03-03&endDate=2026-03-04&regionId=55888&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

Aparthotels

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Condos

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE)

Apartments

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Villas

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## Top Osprey Hotel Reviews

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

### Golden Host Resort - Sarasota

10/10 Excellent

"There was construction happening during my stay so I didn’t get the best experience but with that being said i did have a great time "

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

![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg)

### Carlisle Inn

10/10 Excellent

"All facets of our stay were excellent. Would highly recommend it to anyone."

[](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information)

![Ameniti Bay, BW Signature Collection](https://images.trvl-media.com/lodging/39000000/38800000/38796200/38796114/79763f71_y.jpg)

### Ameniti Bay, BW Signature Collection

10/10 Excellent

"Everything was great."

[](https://expedia.ca/Sarasota-Hotels-Ameniti-Bay.h38796114.Hotel-Information)

![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg)

### The Westin Sarasota

10/10 Excellent

"This was an excellent place to stay."

[](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.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

"Very clean place, super friendly staff. Just a great place to stay."

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

"Love the staff and peaceful vibes. "

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

![Tropical Breeze Resort](https://images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg)

### Tropical Breeze Resort

10/10 Excellent

"Great location. Room was very clean."

[](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.Hotel-Information)

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

### Tropical Beach Resorts

10/10 Excellent

"My husband and I stayed here for 2 nights with our 2 young kids and it was super fun! The rooms are very nice and clean, beds were comfortable, and the kitchen was stocked with everything you’d need. We loved the pool- it was super warm so we could swim even on a cooler day without sun. Highly recommend! "

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

![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg)

### Kompose Boutique Hotel

10/10 Excellent

"Staff was great…room was spotless. Breakfast was great."

[](https://expedia.ca/Sarasota-Hotels-Kompose-Boutique-Hotel.h38215316.Hotel-Information)

## Find out more about Osprey

## Osprey Chalets information

| Number of reviews | 26        |
| ----------------- | --------- |
| Accommodation     | 8 Chalets |
| Lowest Price      | CA $764   |
| Highest Price     | CA $1,716 |

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- [Aparthotels in Nokomis ](https://www.expedia.ca/Nokomis-Apart-Hotels.d10631-aaApartHotels.Travel-Guide-Accommodation)
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- [Hotels near Oscar Scherer State Park ](https://www.expedia.ca/Oscar-Scherer-State-Park-Hotels.0-l6296013-0.Travel-Guide-Filter-Hotels)
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- [Lodges in Polk City ](https://www.expedia.ca/Polk-City-Lodges.d6154853-aaLodges.Travel-Guide-Accommodation)
- [Riads in Polk City ](https://www.expedia.ca/Polk-City-Riads.d6154853-aaRiads.Travel-Guide-Accommodation)
- [Hotel Wedding Venues Hotels in Rivendell ](https://www.expedia.ca/Rivendell-Osprey-Hotels-Wedding-Hotels.0-n553248635976481518-0-tWeddingHotels.Travel-Guide-Filter-Hotels)
- [Rivendell Hotels ](https://www.expedia.ca/Rivendell-Osprey-Hotels.0-n553248635976481518-0.Travel-Guide-Filter-Hotels)
- [Hotels near Sarasota Square ](https://www.expedia.ca/Sarasota-Square-Hotels.0-l553248621563219817-0.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Sorrento Shores ](https://www.expedia.ca/Sorrento-Shores-Osprey-Hotels-Historic-Hotel.0-n553248635976480913-0-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Waterpark Hotels in Sorrento Shores ](https://www.expedia.ca/Sorrento-Shores-Osprey-Hotels-Waterpark-Hotels.0-n553248635976480913-0-tWaterparkHotels.Travel-Guide-Filter-Hotels)
- [Hotels near Stoneybrook Golf & Country Club ](https://www.expedia.ca/Stoneybrook-Golf-Country-Club-Hotels.0-l6068717-0.Travel-Guide-Filter-Hotels)
- [Hotels near The Oaks Club ](https://www.expedia.ca/The-Oaks-Club-Hotels.0-l553248635976489805-0.Travel-Guide-Filter-Hotels)
- [Hotels near Turtle Beach ](https://www.expedia.ca/Turtle-Beach-Hotels.0-l6296228-0.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Vamo ](https://www.expedia.ca/Vamo-Sarasota-Hotels-Beach-Hotel.0-n553248623282278448-0-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Vamo ](https://www.expedia.ca/Vamo-Sarasota-Hotels-Boutique-Hotel.0-n553248623282278448-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Vamo ](https://www.expedia.ca/Vamo-Sarasota-Hotels-Oceanfront-Hotels.0-n553248623282278448-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Vamo Hotels ](https://www.expedia.ca/Vamo-Sarasota-Hotels.0-n553248623282278448-0.Travel-Guide-Filter-Hotels)

- [Visit Casey Key ](https://www.expedia.ca/Casey-Key.dx6167273)
- [Jim Neville Marine Preserve ](https://www.expedia.ca/Jim-Neville-Marine-Preserve-Siesta-Key.d6295999.Vacation-Attraction)
- [Oscar Scherer State Park ](https://www.expedia.ca/Oscar-Scherer-State-Park-Osprey.d6296013.Vacation-Attraction)
- [Visit Rivendell ](https://www.expedia.ca/Osprey-Rivendell.dx553248635976481518)
- [Visit Osprey Village ](https://www.expedia.ca/Osprey-Village.dx553248635976482375)
- [Visit Vamo ](https://www.expedia.ca/Sarasota-Vamo.dx553248623282278448)
- [Stoneybrook Golf & Country Club ](https://www.expedia.ca/Stoneybrook-Golf-Country-Club-Palmer-Ranch.d6068717.Vacation-Attraction)

- [Casey Key Vacation Rentals ](https://www.expedia.ca/Casey-Key-Vacation-Rentals.d6167273.Travel-Guide-VacationRentals)

- [Things to do in Casey Key ](https://www.expedia.ca/Things-To-Do-In-Casey-Key.d6167273.Travel-Guide-Activities)

- [Book Chalets in Osprey on Expedia.com ](https://www.expedia.com/Osprey-Chalets.d55888-aaChalets.Travel-Guide-Accommodation)