Title: Osprey Vacation Rentals from $161: 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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## 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)

![Dining](https://images.trvl-media.com/lodging/121000000/120640000/120633700/120633632/61e8ad11.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)

### 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.

$402 nightly

$448 total

Apr 6 - Apr 7

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/121000000/120690000/120681800/120681763/9ce5bade.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)

### 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.

$424 nightly

$473 total

Apr 6 - Apr 7

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 - 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)

![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)

### 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)

![Interior](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/ca9e4b80.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)

![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)

![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.com/North-Port-Hotels-Charming-Cottage-For-2-Across-Warm-Mineral-Springs-Park.h112257306.Hotel-Information)

9.2/10

Wonderful

(15 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 11 - Mar 12

Total with taxes and fees

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/8b673c78.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)

### 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/72000000/71370000/71365500/71365409/f295aaa1.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)

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

### 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.

$297 nightly

$332 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/273cc0e7.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)

### Vacation Home in Olde Englewood Village

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

9.8/10

Exceptional

(61 reviews)

"Very good, great location 👍👍"

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

James M.

$289 nightly

$323 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.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

(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)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/f0b921dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/9c941b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/9048b0bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/3cde7e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Casey Key

[](https://www.expedia.com/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-A.h83603529.Hotel-Information)

9.4/10

Exceptional

(112 reviews)

"Great location for a quick beach getaway!"

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

Thomas D.

$510 nightly

$570 total

Mar 14 - Mar 15

Total with taxes and fees

[](https://www.expedia.com/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-A.h83603529.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/68000000/67370000/67368800/67368761/14ca75fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/68000000/67370000/67368800/67368761/12d994e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67370000/67368800/67368761/fef5fb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67370000/67368800/67368761/bfb9ccdf.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-3-A-Block-To-The-Beach.h67368761.Hotel-Information)

9.2/10

Wonderful

(70 reviews)

"Second time staying here. Great location. "

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

Nathan H.

$418 nightly

$457 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key-Village-Suite-3-A-Block-To-The-Beach.h67368761.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)

![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)

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

### 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)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/9a646a3f.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)

![Room, 1 King Bed, Pets Not Allowed | Iron/ironing board, free WiFi, bed sheets](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/91000000/90030000/90021900/90021825/78c2df61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Venice Island

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

10/10

Exceptional

(258 reviews)

"Great place! "

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

Michelle

$142 nightly

$161 total

Apr 2 - Apr 3

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/224f0e2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/eea7cfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/14cf5129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/4c4d818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Manasota Key

[](https://www.expedia.com/Englewood-Hotels-Turtle-Cay-At-The-Beach-Shack-Come-On-Down.h76584797.Hotel-Information)

10/10

Exceptional

(44 reviews)

"This was such a cute place to stay rhat is conveniently located via walking diatance to the beach and local restaurants. "

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

Renay S.

$455 nightly

$488 total

Mar 21 - Mar 22

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Turtle-Cay-At-The-Beach-Shack-Come-On-Down.h76584797.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)

![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)

![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)

### 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

$695 nightly

$754 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.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/24000000/23140000/23134800/23134737/6c9396da.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.

$326 nightly

$363 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)

![On the beach, beach umbrellas](https://images.trvl-media.com/lodging/24000000/23550000/23547100/23547098/679f93ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23550000/23547100/23547098/w4176h2736x0y48-e6cea4fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23550000/23547100/23547098/2dc1e0c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23550000/23547100/23547098/617c0dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Longboat Key

[](https://www.expedia.com/Sarasota-Hotels-Silver-Sands-243a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23547098.Hotel-Information)

8.6/10

Excellent

(62 reviews)

"Super beautiful beach and heated pool. So nice. My room had zero view but it was fine. You are there for beach. Not the room. It was clean. Pool was so clear and warm! Coffee pot, refrig and micro all good. Bed was comfy. No sink in apt except bathroom sink. Awkward. But fine. Sunrise to sunset . "

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

Pamela

$299 nightly

$334 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Silver-Sands-243a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23547098.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90210000/90201700/90201631/3bce123d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90210000/90201700/90201631/d43011a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90210000/90201700/90201631/b7c79ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90210000/90201700/90201631/37f08500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Siesta Key

[](https://www.expedia.com/Siesta-Key-Hotels-Lounge-Like-Locals-Walk-To-Siesta-Beach-Bikes.h90201631.Hotel-Information)

9.8/10

Exceptional

(30 reviews)

"The property was very clean and conveniently located ."

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

David

$416 nightly

$428 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-Lounge-Like-Locals-Walk-To-Siesta-Beach-Bikes.h90201631.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)

![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)

![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 9 - Mar 10

Total with taxes and fees

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

![On the beach, beach umbrellas](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032191/a6b424e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032191/69552d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032191/c4a5ffc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032191/565ee5d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Longboat Key

[](https://www.expedia.com/Sarasota-Hotels-Silver-Sands-232-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23032191.Hotel-Information)

9.2/10

Wonderful

(74 reviews)

"Was good. Decent place to work remotely. Open to better rate in the future to stay for a month."

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

Dan S.

$509 nightly

$567 total

Mar 20 - Mar 21

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Silver-Sands-232-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23032191.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)

![Exterior detail](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/887af080.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)

### 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.

$133 nightly

$148 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Riverside-Oasis-1bed1bath.h62599089.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=2026-03-20&endDate=2026-03-21&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=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&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=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=VACATION_HOME)

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=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&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=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=APARTMENT)

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=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&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=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&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=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=APART_HOTEL)

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## Top Osprey Hotel Reviews

![voco Sarasota by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/6f2696b7_y.jpg)

### voco Sarasota by IHG

10/10 Excellent

"Great location, accommodating, nice bar & restaurant "

[](https://expedia.com/Sarasota-Hotels-Voco-Sarasota.h1577382.Hotel-Information)

![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/6dc32504_y.jpg)

### Golden Host Resort - Sarasota

10/10 Excellent

"The room was clean and as expected. Hotel staff were polite and helpful. Check in and out were easy. They even gave us a voucher for two free drinks. Would definitely stay again. "

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

![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/3006ffef_y.jpg)

### Kompose Boutique Hotel

10/10 Excellent

"My boyfriend and I had a short stay. Jeanna was super sweet during check in. The decor is really cute and peppy! The property is clean. Our King room smelt really nice and fresh. AC blew cold, everything was very clean. The towels were plush. The bed to our surprise was very comfy. We did use our own pillows; I can't comment on the comfort of the hotel pillows. TV worked great, signed right into our apps and the hotel did have channels available. Occasionally we heard a plane, the hotel is near the airport one should not expect to not hear one. You will hear the occasional door close, not by fault of the staff. It's a guest not being mindful or the door just getting away from you when coming and going. We did have a room with a balcony which was really nice to have, we like to have coffee in am in the fresh air. There was no coffee maker, we did bring our own. The bathroom, the toilet and shower set up was different. they are separate and private but still a little challenging with the glass sliding door. Cool idea though. We got thru it with no issue as there were only 2 of us. We did not eat at the hotel, i can't comment on the breakfast or restaurant. However, people did look comfortable and happy at the bar/lounge. We would stay at this hotel again. Thank you to Jeanna and all the other friendly staff that made our stay pleasant and stress free. "

[](https://expedia.com/Sarasota-Hotels-Kompose-Boutique-Hotel.h38215316.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

"Room was clean, friendly staff and a nice breakfast. "

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

![Siesta Key Palms Resort](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/0ef16925_y.jpg)

### Siesta Key Palms Resort

10/10 Excellent

" We thoroughly enjoyed our stay at Siesta Key Palm Hotel. Our room was very clean and cozy. Both pools were very clean. The location was perfect-walking distance to the beach. The staff was the best! Everyone was very friendly and helpful. Hopefully we will be back again soon "

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

![Tropical Breeze Resort](https://images.trvl-media.com/lodging/1000000/880000/879700/879629/03ad611d_y.jpg)

### Tropical Breeze Resort

8/10 Good

"Close to sunset beach, can walk to many restaurants, good towels, free parking. Basic room. No microwave, no click, no tissues. Good for a short stay. "

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

![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/f85b62a5_y.jpg)

### Tropical Beach Resorts

8/10 Good

"Beach was so close and convenient to room location. Great pool area. Walking distance to restaurants. Helpful and friendly staff. Clean property and room."

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

![Siesta Key Beach Resort and Suites](https://images.trvl-media.com/lodging/1000000/10000/9600/9560/36292117_y.jpg)

### Siesta Key Beach Resort and Suites

10/10 Excellent

"Pool was nice. Meet several couples to socialize with. Enjoyed happy-hour at the pool. Very clean room. Short walk to most things in the village. "

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

![Hyatt Place Sarasota/Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg)

### Hyatt Place Sarasota/Bradenton Airport

2/10 Terrible

"Husband was injured when the grab bar in the shower came out of the wall"

[](https://expedia.com/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.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 $161 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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- [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)
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- [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

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- [Hotels in Gainesville](https://expedia.com/Gainesville-Hotels.d6048189.Travel-Guide-Hotels)
- [Hotels in Cocoa Beach](https://expedia.com/Cocoa-Beach-Hotels.d6549.Travel-Guide-Hotels)
- [Hotels in West Palm Beach](https://expedia.com/West-Palm-Beach-Hotels.d2742.Travel-Guide-Hotels)
- [Oceanfront Hotels in Destin](https://expedia.com/Destin-Hotels-Oceanfront-Hotels.0-0-d6906-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Destin](https://expedia.com/Destin-Hotels.d6906.Travel-Guide-Hotels)
- [Hotels in Sarasota](https://expedia.com/Sarasota-Hotels.d602719.Travel-Guide-Hotels)
- [Hotels in Naples](https://expedia.com/Naples-Hotels.d602724.Travel-Guide-Hotels)
- [Hotels in Pensacola](https://expedia.com/Pensacola-Hotels.d6023331.Travel-Guide-Hotels)
- [Oceanfront Hotels in Panama City Beach](https://expedia.com/Panama-City-Beach-Hotels-Oceanfront-Hotels.0-0-d8021-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [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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