Title: Osprey Vacation Rentals from $156: 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

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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 three 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)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-07-17&endDate=2026-07-19&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)

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

### Sunny Coastal Escape

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

Bay Acres

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.

$387 nightly

$431 total

Apr 23 - Apr 24

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)

![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/fc1eb47f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Osprey Home

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

Bay Acres

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.

$421 nightly

$469 total

Apr 23 - Apr 24

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) | 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)

![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)

### Tiny House Siesta

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

Sarasota

8.4/10

Very Good

(358 reviews)

"super clean and comfortable. we were 4 people and had a very comfortable and lovely stay. i felt super at home and the location is very centralized to everything "

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

Adanna

$218 nightly

$246 total

Apr 20 - Apr 21

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)

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

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

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/2027abfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming cottage for 2 across warm mineral springs park

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

Warm Mineral Springs

9.2/10

Wonderful

(18 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 26 - Mar 27

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/126000000/125200000/125192200/125192112/1cbee306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125200000/125192200/125192112/32c93334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125200000/125192200/125192112/d30a16ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125200000/125192200/125192112/5bac585b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Fun: Ping Pong, Bbq, Walk to Park Nearby

[](https://www.expedia.com/Sarasota-Hotels-Family-Fun-Ping-Pong.h125192112.Hotel-Information)

Fruitville

$436 nightly

$492 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Family-Fun-Ping-Pong.h125192112.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)

![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)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112260000/112257900/112257831/75202b11.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)

### #3 Small house walking distance to Warm Mineral Spring

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

Warm Mineral Springs

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.

$150 nightly

$167 total

Mar 31 - Apr 1

Total with taxes and fees

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

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

### Nestled in North Port. Updated 2 Bed / 1 Bath.

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

North Port

10/10

Exceptional

(20 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

$223 nightly

$250 total

Mar 25 - Mar 26

Total with taxes and fees

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

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/c128477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/6fb611a7.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)

### Old Floridian cottage in Historic Gulf Village

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

Olde Englewood Village

9.8/10

Exceptional

(61 reviews)

"Very good, great location 👍👍"

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

James M.

$277 nightly

$309 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)

![Interior](https://images.trvl-media.com/lodging/76000000/75200000/75198900/75198846/233aba34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75200000/75198900/75198846/a1874791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75200000/75198900/75198846/7a531b3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75200000/75198900/75198846/597f3a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic cottage, Vamo area, close to beaches, pet friendly, kayaks 

[](https://www.expedia.com/Sarasota-Hotels-Sarasota-Cottage.h75198846.Hotel-Information)

Vamo

9.8/10

Exceptional

(24 reviews)

"Nice place "

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

Viktoriia

[](https://www.expedia.com/Sarasota-Hotels-Sarasota-Cottage.h75198846.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/1d70e05d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/c3560621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/b4e6de67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/35770cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal Quadruplex with private beach access & deck - dog-friendly

[](https://www.expedia.com/Englewood-Hotels-Coastal-Duplex-With-Easement-Access-To-Private-Beach-Deck-Dog-Friendly.h86141519.Hotel-Information)

Manasota Key

8.6/10

Excellent

(13 reviews)

"Great place to stay. "

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

Scott

$381 nightly

$422 total

Apr 4 - Apr 5

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Coastal-Duplex-With-Easement-Access-To-Private-Beach-Deck-Dog-Friendly.h86141519.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)

![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)

### Mimosa Memories 

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

South Venice

9.6/10

Exceptional

(37 reviews)

"Nice house. Very clean. Comfortable bed and linens. Easy check in and out. Convenient location "

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

Kelly

$301 nightly

$337 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Living area](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/7542a46d.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)

![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)

### Kon Tiki Inn

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

Venice Island

10/10

Exceptional

(262 reviews)

"Very nice rooms and close to everything. Owner is very welcoming."

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

Jennifer

$138 nightly

$156 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/20000000/19890000/19887000/19886939/w1350h899x0y1-de204860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/20000000/19890000/19887000/19886939/w1350h899x0y1-fc3beeba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19890000/19887000/19886939/4c792532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/20000000/19890000/19887000/19886939/w1349h899x1y1-2a76d3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset and beach view from your balcony Unit 403

[](https://www.expedia.com/Sarasota-Hotels-Panoramic-Beach-View-And-Amazing-Sunset.h19886939.Hotel-Information)

Longboat Key

9.8/10

Exceptional

(113 reviews)

"Gorgeous view and comfortable interior. Great beach access and good pool. "

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

Tanya M.

$388 nightly

$428 total

Apr 21 - Apr 22

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Panoramic-Beach-View-And-Amazing-Sunset.h19886939.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/127000000/126980000/126976500/126976500/119e155f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/127000000/126980000/126976500/126976500/b9107756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/127000000/126980000/126976500/126976500/ee2533a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/127000000/126980000/126976500/126976500/34d79a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 10 - Pool w/ Slide - Games - 6 Min to IMG

[](https://www.expedia.com/Bradenton-Hotels-Sleeps-10-Pool-W-Slide-Games-6-Min-To-IMG.h126976500.Hotel-Information)

South Bradenton

$443 nightly

$495 total

Apr 21 - Apr 22

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-Sleeps-10-Pool-W-Slide-Games-6-Min-To-IMG.h126976500.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/71000000/70550000/70546800/70546773/9c5bba02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70550000/70546800/70546773/608f5d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/71000000/70550000/70546800/70546773/db4283be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70550000/70546800/70546773/210b1a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

[](https://www.expedia.com/Englewood-Hotels-Beachfront-Condo-With-Beautiful-Views-Of-The-Gulf.h70546773.Hotel-Information)

Manasota Key

9.4/10

Exceptional

(77 reviews)

"Beautiful condo and perfect location for a relaxing beach getaway! We celebrated my husband’s 50th birthday and it was perfect! We will definitely book again! "

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

Yasamin G.

$447 nightly

$495 total

Apr 4 - Apr 5

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Beachfront-Condo-With-Beautiful-Views-Of-The-Gulf.h70546773.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/91000000/90770000/90765900/90765870/678ba916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \[escape to paradise\] siesta key beach getaway

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

Siesta Key

9.8/10

Exceptional

(29 reviews)

"Clean and great location! Would stay again! "

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

Laura W.

$340 nightly

$348 total

Mar 31 - Apr 1

Total with taxes and fees

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

![Smart TV, books, offices](https://images.trvl-media.com/lodging/54000000/53840000/53837600/53837535/745aa44a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/54000000/53840000/53837600/53837535/dd700a2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53840000/53837600/53837535/c09af038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/54000000/53840000/53837600/53837535/77b56aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Getaway, a Boating Paradise

[](https://www.expedia.com/Port-Charlotte-Charlotte-Harbor-Hotels-Pirates-Haunt-On-Lemon-Bay.h53837535.Hotel-Information)

Englewood

10/10

Exceptional

(52 reviews)

"Always an amazing stay"

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

christine w.

$308 nightly

$343 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Port-Charlotte-Charlotte-Harbor-Hotels-Pirates-Haunt-On-Lemon-Bay.h53837535.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/039d040a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/172e7735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/9a1e12a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/7c7c5a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Direct Beachfront 2BR Cottage on Casey Key!

[](https://www.expedia.com/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-B.h83603845.Hotel-Information)

Casey Key

9.2/10

Wonderful

(71 reviews)

"This is a great spot, this was our 2nd time staying and we will definitely be back. "

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

Jason W.

$468 nightly

$524 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-B.h83603845.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/56d6d62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/e47b2b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/0382fa9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/c1b1a163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise Retreat with HEATED POOL-- Need We Say More

[](https://www.expedia.com/Bradenton-Hotels-Paradise-Retreat-With-HEATED-POOL-Need-We-Say-More.h24156060.Hotel-Information)

South Bradenton

10/10

Exceptional

(181 reviews)

"Great location! The host was very responsive. "

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

Ashley G.

$337 nightly

$376 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Bradenton-Hotels-Paradise-Retreat-With-HEATED-POOL-Need-We-Say-More.h24156060.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)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89840000/89835900/89835880/2c2caec8.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)

### Beach Retreat - Completely Renovated!!Half Duplex, WIFI/TV,1mile to Beach.

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

Nokomis

9.4/10

Exceptional

(36 reviews)

"Our stay was lovely and beautiful l. Everything was nice and clean and anywhere we went was only 5 minutes away so the location and neighborhood was great! "

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

Chelsey H.

$354 nightly

$395 total

Mar 28 - Mar 29

Total with taxes and fees

[](https://www.expedia.com/Nokomis-Hotels-New-Listing-Completely-RenovatedHalf-Duplex.h89835880.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=2026-04-07&endDate=2026-04-08&regionId=55888&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CABIN)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CONDO)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APARTMENT)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APART_HOTEL)

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## Top Osprey Hotel Reviews

![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/edd6ba5c_y.jpg)

### Carlisle Inn

10/10 Excellent

"Pool and work out room nice. Breakfast ok"

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

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

### Kompose Boutique Hotel

8/10 Good

"Nice hotel near airport. Clean, friendly. Enjoyed the heated pool & hot tub very much. Breakfast also very good. "

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

![Lantern Inn & Suites](https://images.trvl-media.com/lodging/1000000/450000/448500/448416/8d774750_y.jpg)

### Lantern Inn & Suites

8/10 Good

"This is an older property that has undergone renovations that generally are good. The room was exactly as pictured on the web site and very clean and comfortable, had plenty of towels, and despite being close to the airport, it was quiet enough for undisturbed sleep. A suggestion: install a cabinet to enclose the unit refrigerator and microwave as the refrigerator wobbled when opening the door. The other appliance, assuming it was a dehumidifier did work well as their was no musty smell at all, but it made a good bit of humming noise. Could this be in a cabinet as well somehow? It was a "

[](https://expedia.com/Sarasota-Hotels-Lantern-Inn-Suites.h448416.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 pool was great, the staff was lovely, the floors were slightly dirty "

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

8/10 Good

"The breakfast was very poor, and the person attending the breakfast was not cordial"

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

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

### Tropical Beach Resorts

10/10 Excellent

"More towels in the rooms "

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

"Very quaint property, comfortable and clean. "

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

![Casey Key Resorts - Mainland](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/93021f2f_y.jpg)

### Casey Key Resorts - Mainland

6/10 Okay

"The rooms were a bit dated. Great staff, not so great breakfast"

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

![DoubleTree by Hilton Sarasota Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg)

### DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"We love the hotel super clean and comfortable "

[](https://expedia.com/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.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 $156 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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- [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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