Title: Osprey Vacation Rentals from $232: Search Short-Term Rentals | Expedia.com

[Osprey Travel Guide](https://expedia.com/Osprey.dx55888)[Hotels in Osprey](https://expedia.com/Osprey-Hotels.d55888.Travel-Guide-Hotels)[Flights to Osprey](https://expedia.com/Cheap-Flights-To-Osprey.d55888.Travel-Guide-Flights)[Things to do in Osprey](https://expedia.com/Things-To-Do-In-Osprey.d55888.Travel-Guide-Activities)[Car Rentals in Osprey](https://expedia.com/Car-Rentals-In-Osprey.d55888.Car-Rental-Guide)[Osprey Vacation Packages](https://expedia.com/Osprey.d55888.Destination-Travel-Guides)

![Great Heron](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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We are not like the others - we include taxes and fees

## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/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 three months

[May 22 - May 24](https://www.expedia.com/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)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-06-19&endDate=2026-06-21&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](https://images.trvl-media.com/lodging/121000000/120640000/120633700/120633632/02677d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/121000000/120640000/120633700/120633632/41158187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120640000/120633700/120633632/867eb0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120640000/120633700/120633632/61e8ad11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bay Acres

[](https://www.expedia.com/Osprey-Hotels-Sunny-Coastal-Escape.h120633632.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Great location for exploring north & south! House was very clean and comfy. We appreciated the excellent communication with our nice host, Lynn."

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

Kaja F.

$433 nightly

$483 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Osprey-Hotels-Sunny-Coastal-Escape.h120633632.Hotel-Information)

![Beach towels](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/68ecfea1.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/fc1eb47f.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.com/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.

$455 nightly

$508 total

Mar 25 - Mar 26

Total with taxes and fees

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

![Cabin (Tiny House - Green Lifeguard Stand) | Living area | Flat-screen TV, Netflix, streaming services](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 - Seashell) | Individually decorated, individually furnished, soundproofing, free WiFi](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/564d78d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin (Tiny House - The Siesta) | Individually decorated, individually furnished, soundproofing, free WiFi](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 - The Siesta) | Private kitchen | Fridge, microwave, stovetop, coffee/tea maker](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.com/Sarasota-Hotels-Tiny-House-Siesta.h21430911.Hotel-Information)

8.4/10

Very Good

(352 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

$207 nightly

$233 total

Feb 26 - Feb 27

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/6bac86e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/75202b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/fd10794b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/8b673c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Warm Mineral Springs

[](https://www.expedia.com/North-Port-Hotels-3-Small-House-Walking-Distance-To-Warm-Mineral-Spring.h112257831.Hotel-Information)

9.0/10

Wonderful

(12 reviews)

"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."

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

Jake R.

$150 nightly

$167 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/North-Port-Hotels-3-Small-House-Walking-Distance-To-Warm-Mineral-Spring.h112257831.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/5a3a0e51.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)

### Cottage in Warm Mineral Springs

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

9.0/10

Wonderful

(14 reviews)

"Property was perfect for the price."

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

William M.

$145 nightly

$161 total

Mar 1 - Mar 2

Total with taxes and fees

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

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

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/cfb63e6a.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.com/North-Port-Hotels-Nestled-In-North-Port-Updated-2-Bed-1-Bath.h111593945.Hotel-Information)

10/10

Exceptional

(17 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

$230 nightly

$257 total

Mar 1 - Mar 2

Total with taxes and fees

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

![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)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/5db57a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Venice

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

9.8/10

Exceptional

(19 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

$406 nightly

$453 total

Feb 27 - Feb 28

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/72000000/71370000/71365500/71365409/f295aaa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71370000/71365500/71365409/0525788e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71370000/71365500/71365409/549997df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/72000000/71370000/71365500/71365409/4b024458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in South Venice

[](https://www.expedia.com/Venice-Hotels-Mimosa-Memories.h71365409.Hotel-Information)

9.4/10

Exceptional

(32 reviews)

"Nice quiet home , very clean. "

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

David M.

$292 nightly

$326 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Venice-Hotels-Mimosa-Memories.h71365409.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)

![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/aa27a0eb.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)

### Condo in Manasota Key

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

10/10

Exceptional

(16 reviews)

"Great place and location "

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

Cathy

$657 nightly

$711 total

Feb 27 - Feb 28

Total with taxes and fees

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/79000000/78760000/78759200/78759174/228b5c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78760000/78759200/78759174/86fef44c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78760000/78759200/78759174/711f687c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78760000/78759200/78759174/1fd744f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in South Venice

[](https://www.expedia.com/Venice-Hotels-Coastal.h78759174.Hotel-Information)

9.6/10

Exceptional

(16 reviews)

"We loved this place! It was convenient to everything we liked to do and the perfect size for my husband and I. The bed was comfortable and everything was very clean. "

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

Melissa N.

$435 nightly

$485 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Venice-Hotels-Coastal.h78759174.Hotel-Information)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100400000/100392400/100392339/b63ae16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/101000000/100400000/100392400/100392339/dbe501fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/101000000/100400000/100392400/100392339/18a3aa72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100392400/100392339/9f2f3d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Gulf Gate Estates

[](https://www.expedia.com/Sarasota-Hotels-2-Miles-To-Siesta-Key.h100392339.Hotel-Information)

10/10

Exceptional

(22 reviews)

"Had a great stay! "

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

Keith K.

$148 nightly

$165 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-2-Miles-To-Siesta-Key.h100392339.Hotel-Information)

![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/93000000/92830000/92824800/92824739/c9652d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92830000/92824800/92824739/5c794cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92830000/92824800/92824739/011f3171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/93000000/92830000/92824800/92824739/9da898b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sarasota

[](https://www.expedia.com/Sarasota-Hotels-Beautiful-University-Pines-Studio-In-Sarasota.h92824739.Hotel-Information)

9.8/10

Exceptional

(37 reviews)

"This is our 3rd year staying at this property. We love the location and convince of a quiet neighborhood off university road. We also appreciate the updated amenities and the bed topper is a huge plus for us! "

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

Cecillia C.

$173 nightly

$193 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Beautiful-University-Pines-Studio-In-Sarasota.h92824739.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/9d6a1945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/f3fd974c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/6dfb61f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/88c51812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Longboat Key

[](https://www.expedia.com/Sarasota-Hotels-Cabana-Beach-Club-5b-Suite1-BA-Resort-On-Longboat-Key-By-Rva.h23291227.Hotel-Information)

8.2/10

Very Good

(74 reviews)

"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "

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

K M.

$259 nightly

$289 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Cabana-Beach-Club-5b-Suite1-BA-Resort-On-Longboat-Key-By-Rva.h23291227.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)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/41ec2756.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.com/Bradenton-Hotels-Enjoy-Coastal-Townhome-W-Sunset-Views-Near-The-Gulfs-Most-Popular-Beaches.h107611754.Hotel-Information)

9.8/10

Exceptional

(27 reviews)

"Everything was great!"

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

Lisa and Colin M.

$359 nightly

$401 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/912b5dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/b4af874f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/7da85847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67390000/67389100/67389007/32ecfd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Siesta Key Village

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key-Village-Suite-1-A-Block-To-The-Beach.h67389007.Hotel-Information)

9.8/10

Exceptional

(45 reviews)

"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "

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

Alex

$340 nightly

$369 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key-Village-Suite-1-A-Block-To-The-Beach.h67389007.Hotel-Information)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72570000/72569400/72569341/2205650e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72570000/72569400/72569341/55efd716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/73000000/72570000/72569400/72569341/103120f2_edited_5e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/73000000/72570000/72569400/72569341/f4ccb449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bayshore Gardens

[](https://www.expedia.com/Bradenton-Hotels-Near-To-The-Beach.h72569341.Hotel-Information)

9.2/10

Wonderful

(37 reviews)

"Very nice place, easy check in, and communicative host"

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

Cristopher M.

$155 nightly

$173 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-Near-To-The-Beach.h72569341.Hotel-Information)

![Sun loungers](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/80177dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/5977b0c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/a006d4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/32000000/31820000/31819900/31819843/ca910bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Bradenton

[](https://www.expedia.com/Bradenton-Hotels-Villa-Bella-Executive-2BR-Condo-W2-Pools.h31819843.Hotel-Information)

9.8/10

Exceptional

(135 reviews)

"Only went to pool 1 day as spent most of the time at the beach its a nice area with lots to do and lots of nice walks and great beaches "

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

David C.

$424 nightly

$473 total

Mar 13 - Mar 14

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-Villa-Bella-Executive-2BR-Condo-W2-Pools.h31819843.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/33000000/32800000/32790600/32790513/301d0ceb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/33000000/32800000/32790600/32790513/f78d361f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32800000/32790600/32790513/39236a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32800000/32790600/32790513/93d051ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Gulf Gate Estates

[](https://www.expedia.com/Sarasota-Hotels-Two-Miles-To-Siesta-Key.h32790513.Hotel-Information)

10/10

Exceptional

(46 reviews)

"Terry was a great host. The apartment was very comfortable and had everything we needed for our short stay in Sarasota. Would stay here again."

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

Robert C.

$168 nightly

$187 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Two-Miles-To-Siesta-Key.h32790513.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/86000000/85210000/85206900/85206801/ea08d2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/86000000/85210000/85206900/85206801/e02496f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/86000000/85210000/85206900/85206801/e2e1995f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/86000000/85210000/85206900/85206801/06e4a436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Sarasota

[](https://www.expedia.com/Siesta-Key-Hotels-New-Lower-Prices-Walk-To-Turtle-Beach.h85206801.Hotel-Information)

9.6/10

Exceptional

(14 reviews)

"We had a lovely week in this property and even saw some dolphins swimming by!"

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

Hilda H.

$570 nightly

$635 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-New-Lower-Prices-Walk-To-Turtle-Beach.h85206801.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)

![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)

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

### Vacation Home in Siesta Key

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

9.8/10

Exceptional

(26 reviews)

"Clean and comfortable. "

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

Laney

$438 nightly

$450 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-Modern-Beach-Bungalow-Garden-Views-Patio.h90765870.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.com/Hotel-Search?startDate=2026-03-10&endDate=2026-03-11&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

Condos

[](https://www.expedia.com/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CONDO)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CABIN)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=COTTAGE)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APART_HOTEL)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America&regionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA)

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## Top Osprey Hotel Reviews

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

### The Westin Sarasota

10/10 Excellent

"Room was spotless and the service was amazing. Love this Westin! Always will book a stay. "

[](https://expedia.com/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information)

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

### Tropical Beach Resorts

10/10 Excellent

"Clean room and nice amenities!"

[](https://expedia.com/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.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

"Room was very clean comfortable with all amenities needed "

[](https://expedia.com/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.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

"The room was very clean, as well as rhe grounds. Very spacious. "

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

![Quality Inn Bradenton - Sarasota North](https://images.trvl-media.com/lodging/1000000/20000/16300/16280/839868c9_y.jpg)

### Quality Inn Bradenton - Sarasota North

10/10 Excellent

"Always nice "

[](https://expedia.com/Sarasota-Hotels-Quality-Inn-Bradenton-Sarasota-North.h16280.Hotel-Information)

![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841_y.jpg)

### The St. Regis Longboat Key Resort

10/10 Excellent

"great property great service expensive but worth it in my opinion "

[](https://expedia.com/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.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

"Staff was attentive and courteous. Room was very clean."

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

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

### Lido Beach Resort

10/10 Excellent

"Highly recommend for families "

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

"Spotless room, really clean, nice staff, very well located."

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

## Find out more about Osprey

**Everything you need to know about Osprey vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Osprey vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osprey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $232 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Osprey rentals**

At Expedia, we put the best Osprey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Osprey ](https://expedia.com/Osprey-Private-Vacation-Homes.d55888-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Osprey ](https://expedia.com/Osprey-Condos.d55888-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Osprey ](https://expedia.com/Osprey-Apartments.d55888-aaApartments.Travel-Guide-Accommodation)
- [Villas in Osprey ](https://expedia.com/Osprey-Villas.d55888-aaVillas.Travel-Guide-Accommodation)
- [Cottages in Osprey ](https://expedia.com/Osprey-Cottages.d55888-aaCottages.Travel-Guide-Accommodation)
- [Aparthotels in Osprey ](https://expedia.com/Osprey-Apart-Hotels.d55888-aaApartHotels.Travel-Guide-Accommodation)
- [Resorts in Osprey ](https://expedia.com/Osprey-Resorts.d55888-aaResorts.Travel-Guide-Accommodation)
- [Guest Houses in Osprey ](https://expedia.com/Osprey-Guest-Houses.d55888-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Osprey ](https://expedia.com/Osprey-Motels.d55888-aaMotels.Travel-Guide-Accommodation)
- [Chalets in Osprey ](https://expedia.com/Osprey-Chalets.d55888-aaChalets.Travel-Guide-Accommodation)
- [Houseboats in Osprey ](https://expedia.com/Osprey-Houseboats.d55888-aaHouseboats.Travel-Guide-Accommodation)
- [Farmstay in Osprey ](https://expedia.com/Osprey-Agritourism.d55888-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Osprey ](https://expedia.com/Osprey-Bed-And-Breakfast.d55888-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Osprey ](https://expedia.com/Osprey-Cabins.d55888-aaCabins.Travel-Guide-Accommodation)
- [RV Parks in Osprey ](https://expedia.com/Osprey-RV-Parks.d55888-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Osprey?

### What are some of the best vacation rentals in Osprey?

### How many vacation rentals are there in Osprey?

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

### What’s a vacation rental in Osprey like?

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- [Beach Hotels in Destin](https://expedia.com/Destin-Hotels-Beach-Hotel.0-0-d6906-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Key West](https://expedia.com/Key-West-Hotels.d1187.Travel-Guide-Hotels)
- [Hotels in Tallahassee](https://expedia.com/Tallahassee-Hotels.d6048214.Travel-Guide-Hotels)
- [Oceanfront Hotels in St. Augustine](https://expedia.com/St-Augustine-Hotels-Oceanfront-Hotels.0-0-d6047864-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Siesta Key](https://expedia.com/Siesta-Key-Hotels-Oceanfront-Hotels.0-0-d6881-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Panama City Beach](https://expedia.com/Panama-City-Beach-Hotels.d8021.Travel-Guide-Hotels)
- [Hotels in St. Augustine](https://expedia.com/St-Augustine-Hotels.d6047864.Travel-Guide-Hotels)

Flights

- [Flights to Destin](https://expedia.com/Cheap-Flights-To-Destin.d6906.Travel-Guide-Flights)
- [Flights to Key West](https://expedia.com/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)
- [Flights to Fort Myers](https://expedia.com/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Flights to Daytona Beach](https://expedia.com/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Flights to Sarasota](https://expedia.com/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Flights to Pensacola](https://expedia.com/Cheap-Flights-To-Pensacola.d6023331.Travel-Guide-Flights)

Cars

- [Car rentals in West Palm Beach](https://expedia.com/Car-Rentals-In-West-Palm-Beach.d2742.Car-Rental-Guide)

Packages

- [Key West Vacation](https://expedia.com/Key-West.d1187.Destination-Travel-Guides)
- [Destin Vacation](https://expedia.com/Destin.d6906.Destination-Travel-Guides)

General

- [Visit Santa Rosa Beach](https://expedia.com/Santa-Rosa-Beach.dx183118)

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