Title: Osprey Vacation Rentals from $163: 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 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-06-26&endDate=2026-06-28&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)

![Interior](https://images.trvl-media.com/lodging/121000000/120640000/120633700/120633632/867eb0f5.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/121000000/120640000/120633700/120633632/6413c7f0.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

(4 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.

$419 nightly

$467 total

Mar 31 - Apr 1

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)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/fc1eb47f.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)

![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.

$442 nightly

$493 total

Mar 31 - Apr 1

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 - 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 - 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) | Living area | Flat-screen TV, Netflix, streaming services](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/69212d51.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

$219 nightly

$247 total

Mar 15 - Mar 16

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)

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/7ac2a9bc.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)

### Cottage in Warm Mineral Springs

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

9.2/10

Wonderful

(13 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.

$140 nightly

$156 total

Mar 16 - Mar 17

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)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/2027abfe.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)

### 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.

$140 nightly

$156 total

Mar 6 - Mar 7

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/72000000/71370000/71365500/71365409/6f92c515.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)

### Vacation Home in South Venice

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

9.4/10

Exceptional

(34 reviews)

"Nice quiet home , very clean. "

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

David M.

$306 nightly

$342 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/6732718a.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)

![Dining](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/fcf007c0.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

(18 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

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

![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)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92830000/92824800/92824739/f1592504.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)

### Apartment in Sarasota

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

9.8/10

Exceptional

(39 reviews)

"Perfect area, close to all the stores and restaurants"

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

Maria B.

$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)

![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)

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72570000/72569400/72569341/8bf9dab9.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 21 - Mar 22

Total with taxes and fees

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

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

![Dining](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/34cf9932.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.

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

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/96dfb133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/654d6bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/505b553e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/6e62c16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Bayou Oaks

[](https://www.expedia.com/Sarasota-Hotels-Riverside-Oasis-1bed1bath.h62599089.Hotel-Information)

9.2/10

Wonderful

(46 reviews)

"Excellent place to stay"

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

garry s.

$135 nightly

$150 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Riverside-Oasis-1bed1bath.h62599089.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)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/41ec2756.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)

![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.

$351 nightly

$393 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)

![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/91000000/90770000/90765900/90765870/678ba916.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)

### 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

(27 reviews)

"Clean and comfortable. "

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

Laney

$625 nightly

$645 total

Mar 17 - Mar 18

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/86000000/85210000/85206900/85206801/06e4a436.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)

![Dining](https://images.trvl-media.com/lodging/86000000/85210000/85206900/85206801/e02496f4.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.

$621 nightly

$692 total

Mar 10 - Mar 11

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/101000000/100400000/100392400/100392339/aff37037.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)

![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)

### 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.

$159 nightly

$177 total

Mar 3 - Mar 4

Total with taxes and fees

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

![On the beach](https://images.trvl-media.com/lodging/112000000/111680000/111672200/111672131/9ed1865d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111680000/111672200/111672131/897512cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111680000/111672200/111672131/8fb74e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/112000000/111680000/111672200/111672131/a9a44dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Longboat Key

[](https://www.expedia.com/Longboat-Key-Hotels-Charming-1-Bedroom.h111672131.Hotel-Information)

7.8/10

Good

(11 reviews)

"Amazing property with direct beach access. "

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

maria m.

$326 nightly

$364 total

Mar 13 - Mar 14

Total with taxes and fees

[](https://www.expedia.com/Longboat-Key-Hotels-Charming-1-Bedroom.h111672131.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/90000000/89840000/89835900/89835880/c8c8b17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89840000/89835900/89835880/2bcb80cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89840000/89835900/89835880/ce948254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89840000/89835900/89835880/2c2caec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Nokomis

[](https://www.expedia.com/Nokomis-Hotels-New-Listing-Completely-RenovatedHalf-Duplex.h89835880.Hotel-Information)

9.4/10

Exceptional

(35 reviews)

"Lovely home, great location. We were very comfortable. Since one bedroom had 2 beds, it was perfect for my two sons. Communication with the host was excellent. We enjoyed our stay! "

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

Suzanne R.

$359 nightly

$400 total

Mar 28 - Mar 29

Total with taxes and fees

[](https://www.expedia.com/Nokomis-Hotels-New-Listing-Completely-RenovatedHalf-Duplex.h89835880.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/24000000/23140000/23134800/23134737/022c5a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/24000000/23140000/23134800/23134737/933ff301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23140000/23134800/23134737/0a5e636b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23140000/23134800/23134737/dba385a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Longboat Key

[](https://www.expedia.com/Longboat-Key-Hotels-Cabana-Beach-Club-5-Resort-By-RVA.h23134737.Hotel-Information)

8.8/10

Excellent

(74 reviews)

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The condo was clean and had all that we needed for our two night stay. Loved it will be back again... just a little walk to the beach and some he pool was very nice as well."

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

Nancy C.

$329 nightly

$366 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Longboat-Key-Hotels-Cabana-Beach-Club-5-Resort-By-RVA.h23134737.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32800000/32790600/32790513/39236a2a.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.

$159 nightly

$177 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Beach](https://images.trvl-media.com/lodging/117000000/116550000/116546700/116546614/83643405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/117000000/116550000/116546700/116546614/c2b0345f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116550000/116546700/116546614/b8c072df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116550000/116546700/116546614/e323e842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Longboat Key

[](https://www.expedia.com/Longboat-Key-Hotels-Beachfront-Bliss-On-Longboat-Key-Steps-To-The-Sand.h116546614.Hotel-Information)

7.8/10

Good

(7 reviews)

"Great locale right on the beach "

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

Carole

$329 nightly

$367 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Longboat-Key-Hotels-Beachfront-Bliss-On-Longboat-Key-Steps-To-The-Sand.h116546614.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=2026-03-16&endDate=2026-03-17&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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CONDO)

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME)

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT)

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CABIN)

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE)

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA)

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=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APART_HOTEL)

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## Top Osprey Hotel Reviews

![Siesta Key Beach Resort and Suites](https://images.trvl-media.com/lodging/1000000/10000/9600/9560/993b4c27_y.jpg)

### Siesta Key Beach Resort and Suites

10/10 Excellent

"Location was perfect. Walk across street to beach. Centrally located. Super clean adorable room. Resort staff and owners were amazing "

[](https://expedia.com/Sarasota-Hotels-Siesta-Key-Beach-Resort-Suites-Tiki-Pool.h9560.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

"Location, staff, room are perfect for our needs"

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

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

### Tropical Beach Resorts

10/10 Excellent

"This location is absolutely gorgeous! The front desk staff were very friendly and kind. We were given a map of the property and a list of restaurants and things to do. Their recommendations were spot on! The property is immaculate and our room was clean, comfortable, and just a very short walk to the beach. We can’t wait to come back next year! Thank you to everyone at Tropical Beach Resort!!"

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

![Quality Inn Bradenton - Sarasota North](https://images.trvl-media.com/lodging/1000000/20000/16300/16280/36ea2b32_y.jpg)

### Quality Inn Bradenton - Sarasota North

10/10 Excellent

"The room was much nicer than we expected"

[](https://expedia.com/Sarasota-Hotels-Quality-Inn-Bradenton-Sarasota-North.h16280.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 prompt with requests and great, friendly staff."

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

![Azul Resort Siesta Key](https://images.trvl-media.com/lodging/124000000/123480000/123471600/123471528/3f0a51ef_y.jpg)

### Azul Resort Siesta Key

10/10 Excellent

"The room was perfect and local was awesome! Close to the beach and the village. The front desk staff was very courteous and professional."

[](https://expedia.com/Siesta-Key-Hotels-Azul-Siesta-Key.h123471528.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

"Room was clean. Staff was very friendly and helpful."

[](https://expedia.com/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.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 very helpful. You might want to hire a couple more staff to work the kitchen in the evening. They were great but were a bit overwhelmed by the number of guests to wait on. I give them credit for being so nice under the pressure."

[](https://expedia.com/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

"Really had a nice time staying with tropical breeze location was great close to the beach and close to Siesta Keys Village. Just a personal comment, felt the bed could’ve been in better condition."

[](https://expedia.com/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.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 $163 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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- [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?

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

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- [All-inclusive Resorts in Key West](https://expedia.com/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Daytona Beach](https://expedia.com/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels)
- [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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