Title: Osprey Vacation Rentals from CA $244: Short-Term Rentals for 2026 | Expedia.ca

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![Osprey showing a bay or harbor](https://images.trvl-media.com/place/55888/4df1d5b3-0ca2-4dd3-91c6-479b5ebaf671.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/55888/4df1d5b3-0ca2-4dd3-91c6-479b5ebaf671.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Osprey vacation rentals

![Beach towels](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/68ecfea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/24f433bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/94de1111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/9ce5bade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bay Acres

[](https://www.expedia.ca/Osprey-Hotels-Charming-Osprey-Home.h120681763.Hotel-Information)

10/10

Exceptional

(1 review)

"Upon entering the property, we felt it was clean, bright and very welcoming. We loved the decor and the nice spaces in this two bedroom, two bath home. We thought the location was perfect, right across the main street is Walmart for quick grocery items, and we liked the amenities including a kettle for hot tea, a coffeemaker and a fully equipped kitchen! We would have liked to have more than two beach towels, but we made do with two. The laundry room was convenient for washing clothes and did...

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

Van-Ha N.

CA $270

CA $515 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Osprey-Hotels-Charming-Osprey-Home.h120681763.Hotel-Information)

![Cabin (Tiny House - The Siesta) | Living area](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/69212d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin (Tiny House - The Siesta)](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/13a5c36f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin (Tiny House - Green Lifeguard Stand) | Living area](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/c4c71831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin (Tiny House - The Siesta) | Private kitchen](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/aa92991f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Sarasota

[](https://www.expedia.ca/Sarasota-Hotels-Tiny-House-Siesta.h21430911.Hotel-Information)

8.4/10

Very good

(349 reviews)

"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"

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

Justice

CA $135

CA $317 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Sarasota-Hotels-Tiny-House-Siesta.h21430911.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/ca9e4b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/364b5edc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/5a3a0e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/0a86937c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Warm Mineral Springs

[](https://www.expedia.ca/North-Port-Hotels-Charming-Cottage-For-2-Across-Warm-Mineral-Springs-Park.h112257306.Hotel-Information)

9.2/10

Wonderful

(12 reviews)

"Property was perfect for the price."

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

William M.

CA $95

CA $227 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/North-Port-Hotels-Charming-Cottage-For-2-Across-Warm-Mineral-Springs-Park.h112257306.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/7dab4f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach/ocean view](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/3e26fcd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/08b5bced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Manasota Key

[](https://www.expedia.ca/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information)

10/10

Exceptional

(15 reviews)

"Great place and location "

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

Cathy

CA $270

CA $914 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/a513603c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/fcf007c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/b7c41de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/6732718a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Port

[](https://www.expedia.ca/North-Port-Hotels-Nestled-In-North-Port-Updated-2-Bed-1-Bath.h111593945.Hotel-Information)

10/10

Exceptional

(16 reviews)

"Great place loved how clean and put together everything was would definitely stay here again"

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

Jacob

CA $102

CA $282 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/North-Port-Hotels-Nestled-In-North-Port-Updated-2-Bed-1-Bath.h111593945.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/f85b62a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/cfa0f723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/0e0257b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Room (Specialty Room)](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/7faca073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in South Village

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

9.4/10

Exceptional

(5,269 reviews)

"Wonderful stay!"

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

Victoria

CA $226

CA $291 total

includes taxes & fees

Jan 29 - Jan 30

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/4404083b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/5721262a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/22fd70fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/9eb2951c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Venice

[](https://www.expedia.ca/Venice-Hotels-Myakka-River.h75989217.Hotel-Information)

9.8/10

Exceptional

(18 reviews)

"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "

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

Ty

CA $251

CA $629 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Venice-Hotels-Myakka-River.h75989217.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/9a646a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Pets Not Allowed](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/cc664fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/9b700b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/7542a46d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Venice Island

[](https://www.expedia.ca/Venice-Hotels-Kon-Tiki-Inn.h90021825.Hotel-Information)

10/10

Exceptional

(253 reviews)

"Great place! "

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

Michelle

CA $399

CA $451 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Venice-Hotels-Kon-Tiki-Inn.h90021825.Hotel-Information)

![House, Lakeside | Living area](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/6efe649f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Lake View | Private kitchen](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/e2c2c2f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Lake View | Terrace/patio](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/f4e50887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Lake View | Private kitchen](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/74e8ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Siesta Key

[](https://www.expedia.ca/Sarasota-Hotels-Siesta-Heron-Suites-Villas.h59661429.Hotel-Information)

8.6/10

Excellent

(38 reviews)

"It was perfect for my family of 4 for our beach vacation!!"

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

Jesse

CA $457

CA $790 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Sarasota-Hotels-Siesta-Heron-Suites-Villas.h59661429.Hotel-Information)

![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)

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

![Smart TV, books](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edb5b449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/273cc0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Olde Englewood Village

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

9.8/10

Exceptional

(60 reviews)

"Very good, great location 👍👍"

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

James M.

CA $202

CA $429 total

includes taxes & fees

Feb 1 - Feb 2

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

![Beach nearby, white sand, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/e9ce27d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Living area](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/66da17bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Living area](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/c6eb17ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/816bf8bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Siesta Key

[](https://www.expedia.ca/Sarasota-Hotels-The-Inn-On-Siesta-Key.h9768901.Hotel-Information)

10/10

Exceptional

(194 reviews)

"Very charming place! Great location for the beach and restaurants. Would definitely stay again."

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

Blaine

CA $316

CA $433 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Sarasota-Hotels-The-Inn-On-Siesta-Key.h9768901.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/a321ba46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/9b74f4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/6d40cdb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/e1b5a198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Siesta Key

[](https://www.expedia.ca/Siesta-Key-Hotels-Modern-Beach-Bungalow-Garden-Views-Patio.h90765870.Hotel-Information)

9.8/10

Exceptional

(25 reviews)

"Clean and comfortable. "

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

Laney

CA $139

CA $421 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Siesta-Key-Hotels-Modern-Beach-Bungalow-Garden-Views-Patio.h90765870.Hotel-Information)

![Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/b278ba9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/f710e6e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/e6cbbbd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/4b30e45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Sarasota

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

8.6/10

Excellent

(2,243 reviews)

"Very clean, and staff was extremely nice. "

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

Maribeth

CA $216

CA $244 total

includes taxes & fees

Jan 29 - Jan 30

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

![Property grounds](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/417808cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/6b0ccfab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, free WiFi](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/1743e560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, free cabanas](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/d67a42eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Residences at Siesta Key Beach by Hyatt Vacation Club

[](https://www.expedia.ca/Siesta-Key-Hotels-The-Residences-At-Siesta-Key-Beach-By-Hyatt-Vacation-Club.h3819631.Hotel-Information)

9.6/10

Exceptional

(309 reviews)

"The rooms were perfect, and the staff was great. The location was perfect and peaceful"

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

Marybeth

CA $692

CA $851 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Siesta-Key-Hotels-The-Residences-At-Siesta-Key-Beach-By-Hyatt-Vacation-Club.h3819631.Hotel-Information)

![Deluxe Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/5b42b650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Room](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/1e7203ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/3e86e596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite | Living area](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/37b9a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Siesta Key

[](https://www.expedia.ca/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information)

9.4/10

Exceptional

(89 reviews)

"Very clean very quiet and a great location to the beach."

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

Dave

CA $502

CA $567 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/w827h553x0y17-c69cd501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video library, stereo](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/d102ed59.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)

![Golf](https://images.trvl-media.com/lodging/19000000/18980000/18978100/18978028/da226015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Venice Island

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

9.8/10

Exceptional

(105 reviews)

"Great location and wonderful accommodations. A gem a few blocks walk to the beach. "

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

Cindi B.

CA $217

CA $584 total

includes taxes & fees

Jan 30 - Jan 31

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

![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/w1290h1721x0y538-10bd1239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/0449e44b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/2d0d8eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/71091855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sabal Harbour

[](https://www.expedia.ca/Bradenton-Hotels-Enjoy-Coastal-Townhome-W-Sunset-Views-Near-The-Gulfs-Most-Popular-Beaches.h107611754.Hotel-Information)

10/10

Exceptional

(23 reviews)

"Everything was great!"

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

Lisa and Colin M.

CA $198

CA $513 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Bradenton-Hotels-Enjoy-Coastal-Townhome-W-Sunset-Views-Near-The-Gulfs-Most-Popular-Beaches.h107611754.Hotel-Information)

![447 Avenida De Mayo, Siesta Key, FL W/Pool | Private kitchen](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/d4eb4c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/e92470aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![511 Avenida De Mayo, Siesta Key, FL W/Pool | Living area](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/ad08dd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![711 Beach Rd, Siesta Key, FL No Pool | Living area](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/5e8feac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Siesta Key

[](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Island-Rentals.h89714291.Hotel-Information)

9.6/10

Exceptional

(58 reviews)

"Wonderful stay,Great owners,Fun times"

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

Cornelia

[](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Island-Rentals.h89714291.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83730000/83723400/83723365/42b7f1a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83730000/83723400/83723365/713ca025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/84000000/83730000/83723400/83723365/e237728c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83730000/83723400/83723365/e5695410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in South Venice

[](https://www.expedia.ca/Venice-Hotels-Beautiful-32-Home-With-Heated-Salt-Water-Pool-Minutes-From-The-Beach.h83723365.Hotel-Information)

10/10

Exceptional

(32 reviews)

"It ia a very nice property on a quiet street. Close to all things in Venice. "

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

Shiela H.

CA $268

CA $644 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Venice-Hotels-Beautiful-32-Home-With-Heated-Salt-Water-Pool-Minutes-From-The-Beach.h83723365.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/c947a49f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/f52c1f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/fc05e51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/ba575a6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in South Village

[](https://www.expedia.ca/Sarasota-Hotels-Pool-View-1-King-Bed-Walk-To-Beach-Private-Screen-Porch-Specials-30-OFF.h38441108.Hotel-Information)

9.6/10

Exceptional

(43 reviews)

"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"

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

Dirk T

CA $162

CA $376 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Sarasota-Hotels-Pool-View-1-King-Bed-Walk-To-Beach-Private-Screen-Porch-Specials-30-OFF.h38441108.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=2026-02-11&endDate=2026-02-12&regionId=55888&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Condos

[](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=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=CONDO)

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=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=VACATION_HOME)

Aparthotels

[](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=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=APART_HOTEL)

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=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=COTTAGE)

Apartments

[](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=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=APARTMENT)

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=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=CABIN)

Villas

[](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=2026-04-28&d1=2026-04-28&endDate=2026-05-01&d2=2026-05-01&lodging=VILLA)

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## Top Osprey Hotel Reviews

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

### Lido Beach Resort

10/10 Excellent

"Location was great, staff so positive "

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

"Great clean room! Airport shuttle was super easy and convenient. "

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

![Siesta Key Palms Resort](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda_y.jpg)

### Siesta Key Palms Resort

10/10 Excellent

"Great little resort! Clean and private. Only thing to critique is I wished the pool was warmer, but it was "cold" (60s-70s) while we were there. If it had been 80s-90s the pool would have been perfect. The staff were great and the location is perfect. We will book again! "

[](https://expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information)

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

### Tropical Beach Resorts

10/10 Excellent

"Amazing job"

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

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

### Carlisle Inn

10/10 Excellent

"Bedroom and bathroom very clean and good size. I loved that coffee tea and cookies are available at all times in the lobby. I wish there was a towel bar or hook near the shower to hold the towel or even a small table to put clothes on when coming out of the shower. Location was very convenient. "

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

![The Ritz-Carlton, Sarasota](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d_y.jpg)

### The Ritz-Carlton, Sarasota

10/10 Excellent

"Amenities great, beach club pool was wonderful! Good location, walkable to many restaurants and shops"

[](https://expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.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

"All the above "

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

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

### Kompose Boutique Hotel

10/10 Excellent

"The staff here is excellent and extremely attentive. "

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

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

### Tropical Breeze Resort

10/10 Excellent

"Everything about this resort is great. The staff were friendly and quick. The resort is beautiful, the location is even better and the room is excellent. "

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

## Find out more about Osprey

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Osprey ](https://expedia.ca/Osprey-Private-Vacation-Homes.d55888-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Osprey ](https://expedia.ca/Osprey-Condos.d55888-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Osprey ](https://expedia.ca/Osprey-Apartments.d55888-aaApartments.Travel-Guide-Accommodation)
- [Villas in Osprey ](https://expedia.ca/Osprey-Villas.d55888-aaVillas.Travel-Guide-Accommodation)
- [Cottages in Osprey ](https://expedia.ca/Osprey-Cottages.d55888-aaCottages.Travel-Guide-Accommodation)
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- [Guest Houses in Osprey ](https://expedia.ca/Osprey-Guest-Houses.d55888-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Osprey ](https://expedia.ca/Osprey-Motels.d55888-aaMotels.Travel-Guide-Accommodation)
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- [RV Parks in Osprey ](https://expedia.ca/Osprey-RV-Parks.d55888-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Osprey?

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### What’s there to see and do in Osprey?

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- [Things to do in Boynton Beach](https://expedia.ca/Things-To-Do-In-Boynton-Beach.d6253.Travel-Guide-Activities)
- [Things to do in New Smyrna Beach](https://expedia.ca/Things-To-Do-In-New-Smyrna-Beach.d8943.Travel-Guide-Activities)
- [Things to do in Daytona Beach](https://expedia.ca/Things-To-Do-In-Daytona-Beach.d6023995.Travel-Guide-Activities)
- [Things to do in Naples](https://expedia.ca/Things-To-Do-In-Naples.d602724.Travel-Guide-Activities)
- [Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)
- [Things to do in Cape Coral](https://expedia.ca/Things-To-Do-In-Cape-Coral.d6521.Travel-Guide-Activities)
- [Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)

Packages

- [Key West Vacations](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides)

Vacation Rentals

- [Naples Rentals](https://expedia.ca/Naples-Vacation-Rentals.d602724.Travel-Guide-VacationRentals)

General

- [Visit Cocoa Beach](https://expedia.ca/Cocoa-Beach.dx6549)

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