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 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)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/9ce5bade.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)

### 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.

$363 nightly

$406 total

May 1 - May 2

Total with taxes and fees

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

![Beach](https://images.trvl-media.com/lodging/121000000/120640000/120633700/120633632/02677d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

### Sunny Coastal Escape

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

Bay Acres

10/10

Exceptional

(5 reviews)

$366 nightly

$409 total

May 1 - May 2

Total with taxes and fees

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

![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 - 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)

### 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

$213 nightly

$241 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/113000000/112260000/112257400/112257306/ca9e4b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![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)

### 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

(20 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)

![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)

![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)

### 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.

$251 nightly

$280 total

May 1 - May 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/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/72000000/71370000/71365500/71365409/0525788e.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)

"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "

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

Alexus

$294 nightly

$328 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76800000/76790800/76790733/82ee712a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76800000/76790800/76790733/75b33826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76800000/76790800/76790733/eb40a681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/77000000/76800000/76790800/76790733/9297a356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

[](https://www.expedia.com/Sarasota-Hotels-Centrally-Located-20-Minutes-To-Siesta-And-St-Armands-10-Minutes-To-Downtown.h76790733.Hotel-Information)

Southgate

10/10

Exceptional

(71 reviews)

"Wonderful Stay"

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

Christopher R.

$243 nightly

$272 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Centrally-Located-20-Minutes-To-Siesta-And-St-Armands-10-Minutes-To-Downtown.h76790733.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/127000000/126160000/126159400/126159349/b17df87d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/127000000/126160000/126159400/126159349/b9839f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/127000000/126160000/126159400/126159349/890decf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/127000000/126160000/126159400/126159349/3672e8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Path to Paradise.

[](https://www.expedia.com/Englewood-Hotels-Path-To-Paradise.h126159349.Hotel-Information)

Olde Englewood Village

$274 nightly

$306 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Path-To-Paradise.h126159349.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)

![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)

![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)

"Beach and beach view were amazing! Felt like we had our own private beach. Beautiful sunsets."

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

Denise 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)

![Beach](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/56d6d62b.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)

![Interior](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/e47b2b85.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)

"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.

$316 nightly

$354 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](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/2473d6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/445f0446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/6cd9aa80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/57000000/56840000/56833500/56833487/f9344416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flamingo's Nest at the Beach Shack. Just one block from the beach!

[](https://www.expedia.com/Englewood-Hotels-Flamingos-Nest-At-The-Beach-Shack-Just-One-Block-From-The-Beach.h56833487.Hotel-Information)

Manasota Key

10/10

Exceptional

(41 reviews)

"Location was great, property condition is excellent!"

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

Mabel

$381 nightly

$406 total

Apr 29 - Apr 30

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Flamingos-Nest-At-The-Beach-Shack-Just-One-Block-From-The-Beach.h56833487.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)

![Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/9b700b6f.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)

"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"

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

Carolyn

$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)

![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)

![Interior](https://images.trvl-media.com/lodging/77000000/76590000/76584800/76584797/a97d489f.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)

### Turtle Cay at The Beach Shack! Come On Down!

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

Manasota Key

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.

$383 nightly

$408 total

Apr 29 - Apr 30

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/b8cf3ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/79b84ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/63d239fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/11e2004b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gulf Coast Escape · IMG Academy · Dual Pools & Hot Tubs · Anna Maria Island

[](https://www.expedia.com/Sarasota-Hotels-Newly-Listed-Upgraded-Waterfront-Condonear-Beachesimg-Academyanna-Mariasrq.h41375487.Hotel-Information)

Bradenton

9.8/10

Exceptional

(118 reviews)

"We had a fantastic stay! The condo is beautiful, spacious, and extremely comfortable. Perfect for relaxing and feeling right at home. Ervin (host) was professional, kind, and very accommodating, making communication easy and the entire experience seamless. We’re truly thankful for such a wonderful stay and would highly recommend this property."

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

Parker S.

$280 nightly

$314 total

Apr 27 - Apr 28

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Newly-Listed-Upgraded-Waterfront-Condonear-Beachesimg-Academyanna-Mariasrq.h41375487.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/105000000/104730000/104729900/104729878/ad46e0ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/105000000/104730000/104729900/104729878/9e5a2a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104730000/104729900/104729878/7181c542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104730000/104729900/104729878/4491864b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Beach House Just Minutes From Siesta Key

[](https://www.expedia.com/Sarasota-Hotels-Cozy-Beach-House-Just-Minutes-From-Siesta-Key.h104729878.Hotel-Information)

Sarasota

9.0/10

Wonderful

(13 reviews)

"Great location, family friendly! "

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

Lyna T.

$293 nightly

$329 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Cozy-Beach-House-Just-Minutes-From-Siesta-Key.h104729878.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)

![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)

![Dining](https://images.trvl-media.com/lodging/93000000/92830000/92824800/92824739/5c794cdb.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.

$190 nightly

$212 total

Apr 28 - Apr 29

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/91000000/90770000/90765900/90765870/9b74f4a5.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.

$401 nightly

$412 total

Apr 6 - Apr 7

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/08b5bced.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)

### Chadwick Cove Resort & Marina

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

Manasota Key

10/10

Exceptional

(17 reviews)

"Great place and location "

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

Cathy

$640 nightly

$692 total

Apr 4 - Apr 5

Total with taxes and fees

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70550000/70546800/70546773/e0ab88c6.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)

### 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)

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=2026-04-14&endDate=2026-04-15&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&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

"Our room was very clean and large. All appliances have been updated including the in room large washer and dryer. I wrote down our room number for any travel plans in the future. I would definitely stay here again. "

[](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

"room was clean, the staff friendly, parking safe. Only suggestion is dish drying rack and cutting board would be helpful. Other than that we will be back."

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

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

### Kompose Boutique Hotel

10/10 Excellent

"Great hotel, very close to the airport so very convenient. Very clean, updated and nicely decorated. Good food at the restaurant. "

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

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

### Casey Key Resorts - Mainland

10/10 Excellent

"A little updating needed other than that food was great, room and hotel areas very clean "

[](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

"Came to Sarasota for the weekend and got on Expedia to find me a decent deal with a high rating. This place came up and at an affordable price. I liked how a lot of different restaurants and things to do were near. The beaches are about 20-30 minutes away and the locals were very friendly! The hotel employees were very friendly as well. They had a tiki bar right on the property near the pool. The pool was nice, clean and maintained, we very much enjoyed it. The room was very nice and spacious! The bathroom had so much space, it was definitely a PLUS!! The tv was a good size and kept updated. Overall a well maintained place and I would book again with them in the future. Wish I took pictures…. "

[](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

8/10 Good

"Love the old Florida vibe where people are friendly and talk to each other. The staff that work there are great, parking is easy, and the retro looking appliances in the rooms are really unique."

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

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

### Azul Resort Siesta Key

6/10 Okay

"The room was clean and new. The location was perfect. However the shower was flooding the bathroom to the point where it was reaching the threshold into the room. I contacted the staff who sent a maintenace person. The said the shower was missing some kind of gasket. I also think it was not draining properly. I ask for more towels to contain the water but they did not bring enough . In fact they brought kess including no rags. By day 3 it was really. One time i called and the person at the desk was sort of rude saying they could check me out like i had somewhere else to ho. Finally a different maintenace guy showed up and was able to piece meal some stuff from other showers. It did not totally solve the problem but it was better. Finally later that night they brought sufficent towels but was leaving the next day. The whole experience just distracted from my vacation. I have text and pictures as that is how you interact with the desk. I would also recommend a microwave and a long mirror. Overall the place is nice but unfortunately my stay was not up to par because of the shower."

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

## 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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- [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)
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- [RV Parks in Osprey ](https://expedia.com/Osprey-RV-Parks.d55888-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

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- [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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