Title: Osprey Vacation Rentals from $152: 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 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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 three 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)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-07-24&endDate=2026-07-26&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)

### Sunny Coastal Escape

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

Bay Acres

10/10

Exceptional

(5 reviews)

$374 nightly

$417 total

Apr 27 - Apr 28

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)

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

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

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

(2 reviews)

"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "

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

Diane S.

$369 nightly

$412 total

Apr 27 - Apr 28

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) | 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 - 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)

### Tiny House Siesta

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

Sarasota

8.4/10

Very Good

(359 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

$206 nightly

$233 total

Apr 12 - Apr 13

Total with taxes and fees

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

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123300000/123296500/123296439/d1a390e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123300000/123296500/123296439/ad0e4a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123300000/123296500/123296439/dce0ab6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123300000/123296500/123296439/630678d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5 Mi to Golf & Trails: North Port Retreat w/ Pool

[](https://www.expedia.com/North-Port-Hotels-5-Mi-To-Golf-Trails-North-Port-Retreat-W-Pool.h123296439.Hotel-Information)

North Port

10/10

Exceptional

(1 review)

"The house had everything we needed, great location & neighborhood also."

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

Gina

[](https://www.expedia.com/North-Port-Hotels-5-Mi-To-Golf-Trails-North-Port-Retreat-W-Pool.h123296439.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)

![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)

### #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)

"My favorite place to stay when I come to visit my aunt! It’s comfy, clean and perfect location! I’ll be booking again in June. This was my 4 stay I think! You have all you need, and a quiet location. It truly is a gem! "

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

BABS G.

$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)

![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)

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

$276 nightly

$308 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/113000000/112260000/112257400/112257306/ca9e4b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

![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

(19 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

Apr 5 - Apr 6

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/72000000/71370000/71365500/71365409/0525788e.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)

### 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

$294 nightly

$328 total

Apr 12 - Apr 13

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)

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

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/cfb63e6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### 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

$197 nightly

$220 total

Apr 1 - Apr 2

Total with taxes and fees

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

![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)

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

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

### Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

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

Sabal Harbour

10/10

Exceptional

(30 reviews)

"Everything was great!"

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

Lisa and Colin M.

$318 nightly

$356 total

Apr 21 - Apr 22

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)

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

![Room, 1 King Bed, Pets Not Allowed | 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)

![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)

### Kon Tiki Inn

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

Venice Island

10/10

Exceptional

(264 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

$134 nightly

$152 total

Apr 8 - Apr 9

Total with taxes and fees

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

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

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

![Exterior](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/6d40cdb5.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.

$281 nightly

$287 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)

![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)

![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)

![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)

### Beautiful University Pines Studio in Sarasota

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

Sarasota

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.

$185 nightly

$207 total

Apr 29 - Apr 30

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/84000000/83610000/83603900/83603845/039d040a.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)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/40337104.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)

### 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.

$481 nightly

$537 total

Mar 31 - Apr 1

Total with taxes and fees

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19890000/19887000/19886939/w1349h899x1y1-5b522171.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)

![TV, offices](https://images.trvl-media.com/lodging/127000000/126980000/126976500/126976500/34712abb.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)

![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)

### 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

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

### 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

9.6/10

Exceptional

(37 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.

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

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/54000000/53840000/53837600/53837535/ca256c6e.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.

$305 nightly

$340 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)

![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)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/9a021a34.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)

### 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)

"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "

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

David S.

$346 nightly

$386 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)

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

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

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

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

### Siesta Key Village-Suite #1: A block to the Beach!

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

Siesta Key Village

9.8/10

Exceptional

(45 reviews)

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

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

Alex

[](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key-Village-Suite-1-A-Block-To-The-Beach.h67389007.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=2026-04-13&endDate=2026-04-14&regionId=55888&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=CABIN)

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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=COTTAGE)

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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APART_HOTEL)

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=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APARTMENT)

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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

"Had a lovely 2 night stay at the hotel. Breakfast was good and fresh. Had one traveler who would have liked bacon instead of sausage. Was very touched to have two cupcakes waiting in the room as it was my birthday the day we arrived. Lovely staff and very accommodating. Would definitely stay again when in the area."

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

"Great staff, cool amenities, room had a good size patio area in the back"

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

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

### Golden Host Resort - Sarasota

4/10 Poor

" No TV service available, air conditioner was on full speed 60 degree room and the door rattled from it , turned it down and then did not work. Walls thin we could hear people yelling and swearing outside. Stayed before flying out in the morning did not get much sleep. "

[](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

4/10 Poor

"Amazing staff. Unfortunately Tub backed up & pool drinks were overpriced, no clean pool towels in bin first evening, hot tub jets didn’t work."

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

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

### Tropical Breeze Resort

10/10 Excellent

"Really nice stay. Everyone was super friendly and room was clean. I love that they give beach chairs, beach towels, beach toys for kids, and bikes for free!! Perfect 3 day stay. "

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

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

### Casey Key Resorts - Mainland

4/10 Poor

"Rooms give ‘spartan’ a whole new meaning. Only one chair to sit on. No shelf space in the bathroom. "

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

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

### Lantern Inn & Suites

10/10 Excellent

"Great stay. Would stay here again."

[](https://expedia.com/Sarasota-Hotels-Lantern-Inn-Suites.h448416.Hotel-Information)

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

### Kompose Boutique Hotel

10/10 Excellent

"Clean, friendly staff, great pool area. Quiet in rooms. "

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

8/10 Good

"If you’re looking for a laid back option within walking distance to the beach and village it is a convenient place to stay. The room amenities are very limited so make sure you come prepared. "

[](https://expedia.com/Sarasota-Hotels-Siesta-Key-Beach-Resort-Suites-Tiki-Pool.h9560.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 $152 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)
- [Cabin Rentals in Osprey ](https://expedia.com/Osprey-Cabins.d55888-aaCabins.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)
- [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 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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