Title: Osprey Vacation Rentals from $143: 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 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-07-31&endDate=2026-08-02&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

![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

(266 reviews)

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

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

Carolyn

$127 nightly

$143 total

May 4 - May 5

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/f85b62a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/28955014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/0e0257b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/cfa0f723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropical Beach Resorts

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

South Village

9.4/10

Exceptional

(5,399 reviews)

"Love the location, excellent service and place clean and quite "

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

Dayami

$226 nightly

$256 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Apartment (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/126000000/125340000/125334400/125334398/9f5d66bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125340000/125334400/125334398/160a69b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125340000/125334400/125334398/40bedc4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125340000/125334400/125334398/ee51b81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4 Mi to Siesta Key Beach: Condo w/ Private Patio

[](https://www.expedia.com/Sarasota-Hotels-4-Mi-To-Siesta-Key-Beach-Condo-W-Private-Patio.h125334398.Hotel-Information)

Sarasota

$309 nightly

$345 total

Apr 19 - Apr 20

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-4-Mi-To-Siesta-Key-Beach-Condo-W-Private-Patio.h125334398.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/8eb985bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Large 2 Bedrooms, 1 Bath, Kitchen, Patio | Living area | 42-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/95eba461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/e476cb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/1ea9ff08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Venice Beach Villas

[](https://www.expedia.com/Sarasota-Hotels-Venice-Beach-Villas.h7806268.Hotel-Information)

Venice Island

9.4/10

Exceptional

(478 reviews)

"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."

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

Kathy

$132 nightly

$149 total

Apr 27 - Apr 28

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Venice-Beach-Villas.h7806268.Hotel-Information)

![Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/31f9068d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/fa86635e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bayside Two Bedroom | Premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/c30fa425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/6e093d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Beach Retreat

[](https://www.expedia.com/Sarasota-Hotels-A-Beach-Retreat.h1533163.Hotel-Information)

Casey Key

9.2/10

Wonderful

(619 reviews)

"Love this place"

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

Marialis

$189 nightly

$214 total

May 3 - May 4

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-A-Beach-Retreat.h1533163.Hotel-Information)

![Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/b278ba9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed | Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/bf379373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/e6cbbbd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/4b30e45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hibiscus Suites - Gateway to Siesta Key

[](https://www.expedia.com/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information)

Sarasota

8.6/10

Excellent

(2,275 reviews)

"Clean room, quiet and in a location convenient to Siesta Key. The pool is very nice, although located at the front of the property alongside a busy road. Would definitely recommend this hotel, especially if a kitchenette is desired."

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

CAROLYN

$179 nightly

$202 total

Apr 19 - Apr 20

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information)

![Luxury Condo, Beach View | Balcony](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/5a945c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Condo, Beach View | Living area | 65-inch Smart TV with cable channels, Netflix, streaming services](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/1787b77c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Condo, Beach View | Beach/ocean view](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/6b262d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Condo, Beach View | Room amenity](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/a2a79e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gulf View Condominiums

[](https://www.expedia.com/Englewood-Hotels-Gulf-View-Condominiums.h113003026.Hotel-Information)

Manasota Key

$896 nightly

$973 total

Apr 15 - Apr 16

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Gulf-View-Condominiums.h113003026.Hotel-Information)

![House, 2 Bedrooms, Pets Allowed | Private kitchen](https://images.trvl-media.com/lodging/120000000/119530000/119524700/119524619/w1342h899x1y1-640f2edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 2 Bedrooms, Pets Allowed | Living room](https://images.trvl-media.com/lodging/120000000/119530000/119524700/119524619/w1349h899x1y1-5ffe7771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/120000000/119530000/119524700/119524619/1c6557ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 2 Bedrooms, Pets Allowed | Dining room](https://images.trvl-media.com/lodging/120000000/119530000/119524700/119524619/w1350h899x0y1-45181973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal 2-Bedroom Home Minutes to Beach

[](https://www.expedia.com/Englewood-Hotels-Coastal-2-Bedroom-Home-Minutes-To-Beach.h119524619.Hotel-Information)

Englewood Central

10/10

Exceptional

(3 reviews)

"Great space- had everything needed to enjoy a beach stay"

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

Adriana

$373 nightly

$421 total

Apr 10 - Apr 11

Total with taxes and fees

[](https://www.expedia.com/Englewood-Hotels-Coastal-2-Bedroom-Home-Minutes-To-Beach.h119524619.Hotel-Information)

![Beach nearby, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/2173fe57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/262d7ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/8c067bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/2f75b114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropical Villas of Venice Beach

[](https://www.expedia.com/Sarasota-Hotels-Tropical-Villas-Of-Venice-Beach.h37877891.Hotel-Information)

Venice Island

9.6/10

Exceptional

(245 reviews)

"Staff very accommodating."

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

Genevieve

$204 nightly

$230 total

Apr 22 - Apr 23

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Tropical-Villas-Of-Venice-Beach.h37877891.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/126000000/125200000/125193200/125193186/aa3b5688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125200000/125193200/125193186/e22c3b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125200000/125193200/125193186/df44450c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125200000/125193200/125193186/75eadc07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Retro Vibes Private BBQ & Beach Access

[](https://www.expedia.com/Sarasota-Hotels-Stylish-Retro-Vibes-Private-BBQ-Beach-Access.h125193186.Hotel-Information)

Sarasota

$335 nightly

$378 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Stylish-Retro-Vibes-Private-BBQ-Beach-Access.h125193186.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

(362 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

$195 nightly

$220 total

Apr 27 - Apr 28

Total with taxes and fees

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3d46ab53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/4232d07e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hideaway Studio | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/018c8641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Captiva Beach Resort

[](https://www.expedia.com/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information)

South Village

9.0/10

Wonderful

(1,224 reviews)

"Clean and very close to beach. "

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

Daniel

$251 nightly

$281 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information)

![Luxury Condo, 2 Bedrooms, Non Smoking, Pets Allowed | Dining](https://images.trvl-media.com/lodging/128000000/127720000/127715900/127715802/182b1774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/128000000/127720000/127715900/127715802/4c06aae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Condo, 2 Bedrooms, Non Smoking, Pets Allowed | Private kitchen](https://images.trvl-media.com/lodging/128000000/127720000/127715900/127715802/20943d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Condo, 2 Bedrooms, Non Smoking, Pets Allowed](https://images.trvl-media.com/lodging/128000000/127720000/127715900/127715802/23920616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cedar Run Resort - Roam Hospitality

[](https://www.expedia.com/Bradenton-Hotels-Cedar-Run-Resort-Roam-Hospitality.h127715802.Hotel-Information)

South Bradenton

[](https://www.expedia.com/Bradenton-Hotels-Cedar-Run-Resort-Roam-Hospitality.h127715802.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124320000/124319700/124319650/4e638c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124320000/124319700/124319650/9a799276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124320000/124319700/124319650/580265fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124320000/124319700/124319650/ac55bbfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unwind Poolside + Walk to Beach! Sarasota Retreat

[](https://www.expedia.com/Siesta-Key-Hotels-Unwind-Poolside-Walk-To-Beach-Sarasota-Retreat.h124319650.Hotel-Information)

South Village

8.0/10

Very Good

(1 review)

"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "

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

Eleuterio

[](https://www.expedia.com/Siesta-Key-Hotels-Unwind-Poolside-Walk-To-Beach-Sarasota-Retreat.h124319650.Hotel-Information)

![Beach nearby, white sand, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/e9ce27d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Living area | 65-inch Smart TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/c6eb17ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/cdf5ba63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/c4a745ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn On Siesta Key

[](https://www.expedia.com/Sarasota-Hotels-The-Inn-On-Siesta-Key.h9768901.Hotel-Information)

Siesta Key

10/10

Exceptional

(196 reviews)

"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"

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

Amanda

$356 nightly

$402 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-The-Inn-On-Siesta-Key.h9768901.Hotel-Information)

![Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/5b42b650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite | Living area | TV](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/37b9a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Room | In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/1e7203ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/3e86e596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SeaSpray Resort

[](https://www.expedia.com/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information)

Siesta Key

9.6/10

Exceptional

(105 reviews)

"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "

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

Jayline

$278 nightly

$314 total

May 3 - May 4

Total with taxes and fees

[](https://www.expedia.com/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information)

![House | 3 bedrooms](https://images.trvl-media.com/lodging/124000000/123800000/123796300/123796255/w2499h1663x1y1-542562cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 3 bedrooms](https://images.trvl-media.com/lodging/124000000/123800000/123796300/123796255/w2499h1665x1y1-132fb834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 3 bedrooms](https://images.trvl-media.com/lodging/124000000/123800000/123796300/123796255/w2499h1663x1y1-f773ad48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 3 bedrooms](https://images.trvl-media.com/lodging/124000000/123800000/123796300/123796255/w2499h1663x1y1-14faaac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 8 Pets Welcome Fenced In Backyard

[](https://www.expedia.com/Sarasota-Hotels-Sleeps-8-Pets-Welcome-Fenced-In-Backyard.h123796255.Hotel-Information)

Southgate

$329 nightly

$371 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Sleeps-8-Pets-Welcome-Fenced-In-Backyard.h123796255.Hotel-Information)

![House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/6efe649f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Lake View | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/1ca731da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Lake View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/74e8ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Lake View | Terrace/patio](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/f4e50887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Siesta Heron Suites & Villas

[](https://www.expedia.com/Sarasota-Hotels-Siesta-Heron-Suites-Villas.h59661429.Hotel-Information)

Siesta Key

8.4/10

Very Good

(41 reviews)

"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"

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

Christopher Robert

$318 nightly

$360 total

Apr 28 - Apr 29

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Siesta-Heron-Suites-Villas.h59661429.Hotel-Information)

![Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/f7199cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/177419d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/cb4785e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/9c797865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lulu's Key House Leatherback 2/2 Downstairs

[](https://www.expedia.com/Sarasota-Hotels-Lulus-Key-House-Leatherback-22-Downstairs.h67211563.Hotel-Information)

Siesta Key Village

$630 nightly

$709 total

May 2 - May 3

Total with taxes and fees

[](https://www.expedia.com/Sarasota-Hotels-Lulus-Key-House-Leatherback-22-Downstairs.h67211563.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122300/125122253/377f07d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122300/125122253/534a330b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122300/125122253/d2600988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122300/125122253/bcd680ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artsy Getaway With Vibrant Design Flair

[](https://www.expedia.com/Sarasota-Hotels-Artsy-Getaway-With-Vibrant-Design-Flair.h125122253.Hotel-Information)

Arlington Park

[](https://www.expedia.com/Sarasota-Hotels-Artsy-Getaway-With-Vibrant-Design-Flair.h125122253.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=2026-04-22&endDate=2026-04-23&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=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&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=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&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=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&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=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&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=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&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=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&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=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&lodging=APARTMENT)

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## Top Osprey Hotel Reviews

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

### Tropical Beach Resorts

10/10 Excellent

"Very clean, Staff was very friendly and helpful "

[](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

"This hotel was very clean and quaint. You felt like you were very secluded and had so many amenities."

[](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

8/10 Good

"Great place"

[](https://expedia.com/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.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 amenities! "

[](https://expedia.com/Sarasota-Hotels-Kompose-Boutique-Hotel.h38215316.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 only issue i had was that the lights outside the door shine through the frostwd window at top of door. Hard for me to fall asleep since I am accustomed to a dark room. A shade to darken would be helpful. Thank you"

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

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

### Siesta Key Beach Resort and Suites

10/10 Excellent

"Laundry was convenient and kitchen had the necessities. "

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

![Cirque St. Armands Beachside](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/a1349b0e_y.jpg)

### Cirque St. Armands Beachside

10/10 Excellent

"The staff was incredible. They were so helpful and accommodating. Texting with the front desk was the icing on the cake."

[](https://expedia.com/Sarasota-Hotels-Cirque-St-Armands-Beachside.h22224.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

"Good option, clean, updated and friendly staff"

[](https://expedia.com/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information)

![The Ritz-Carlton, Sarasota](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d_y.jpg)

### The Ritz-Carlton, Sarasota

10/10 Excellent

"Great location and a quick shuttle ride to the beautiful Lido beach. The staff at the beach club were great, especially Lea! I went for a girls trip but definitely couples and family friendly. I will definitely be back."

[](https://expedia.com/Sarasota-Hotels-The-Ritz-Carlton.h806101.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 $143 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)
- [Houseboats in Osprey ](https://expedia.com/Osprey-Houseboats.d55888-aaHouseboats.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

### Can I find vacation rentals in Osprey?

### What are some of the best vacation rentals in Osprey?

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

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### Expedia's Latest Trends

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- [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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