Osprey Vacation Rentals from ₩111,733: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Osprey?

Charming Florida Beach Home w King Bed Patio : Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

Check prices for these dates

In two weeks

In one month

In two months

In three months

Vacation Rentals in Osprey

"The best place to stay! Super clean home and friendly service. I would stay here again. "

₩440,295 total

includes taxes & fees

Aug 25 - Aug 26

Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

"Very Nice Resort!"

₩251,552 total

includes taxes & fees

Sep 1 - Sep 2

"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "

₩329,849 total

includes taxes & fees

Sep 1 - Sep 2

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

"Bed comfort , great location, friendly staff. "

₩187,918 total

includes taxes & fees

Aug 24 - Aug 25

"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "

₩362,870 total

includes taxes & fees

Aug 22 - Aug 23

"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."

₩278,900 total

includes taxes & fees

Aug 24 - Aug 25

Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

"Super helpful staff."

₩205,170 total

includes taxes & fees

Aug 26 - Aug 27

"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"

"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"

₩219,658 total

includes taxes & fees

Aug 24 - Aug 25

"An outstanding experience — a place that leaves you with a strong desire to return."

"Great location. Everyone was very friendly and accommodating!"

₩824,588 total

includes taxes & fees

Aug 28 - Aug 29

"Easy walk or bike ride to beach. Property has plenty of bikes to borrow with locks. Overall just super place that I’ll stay again. "

"Absolutely beautiful location has everything you need n makes you feel like home"

322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "

Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

"Great place to stay! "

₩507,146 total

includes taxes & fees

Aug 23 - Aug 24

Beach nearby, beach umbrellas, beach towels

"Great Location !!"

Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop

"It was perfect for my family of 4 for our beach vacation!!"

₩482,522 total

includes taxes & fees

Aug 24 - Aug 25

"Nic place to stay and enjoy the area"

₩760,460 total

includes taxes & fees

Aug 27 - Aug 28

Deluxe Studio, Bay View | View from room

"Cute place and property! Cozy, quiet and clean. The property manager was very nice. We enjoyed the private beach on the property. It is walking distance to 2 restaurants. Would def go back, we had a nice relaxing weekend. "

₩313,201 total

includes taxes & fees

Aug 22 - Aug 23

"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Osprey Hotel Reviews

Carlisle Inn

10/10 Excellent

"It’s a perfect little gem!"

Tropical Beach Resorts

10/10 Excellent

"We had a wonderful stay here everything about the property was great one minor gripe was the amount of glass being allowed in the pool and also security didn’t do enough to Stop it a huge family arrived one day eating drinking in the pool if you have pool rules stick to them . Get rid of wristbands "

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"I had an absolutely wonderful stay at this hotel. From the moment I arrived, the staff went above and beyond to make me feel welcome. The check-in process was quick and easy, and I was greeted with a warm smile. The room was spotless, beautifully decorated, and very comfortable. The bed felt like sleeping on a cloud, and the view from my window was breathtaking. I also appreciated the small details—fresh towels, complimentary water, and excellent Wi-Fi. The amenities were top-notch. The pool area was clean and relaxing, and the fitness center had everything I needed. Breakfast each morning was delicious with plenty of variety, and the restaurant service was outstanding. What stood out the most was the staff’s hospitality. Everyone was friendly, attentive, and truly cared about making my stay perfect. I couldn’t have asked for a better experience. I highly recommend this hotel to anyone visiting the area. I’ll definitely be coming back!"

Golden Host Resort - Sarasota

10/10 Excellent

"This is such a fun property to stay at. The pool is huge and salt water. The rooms are decorated midcentury modern which is pretty cool. We had a balcony on second floor which was great to sit outside on for a breeze. Air conditioner worked well. We loved the tiki bar next door, and the food truck across the street will blow your mind. The rooms were clean, but outside could definitely use a cleaning. But dont let that worry you. We bought a few souvenirs the night we checked in.. and by the next morning on wednesday i wished i had more.. but they dont let the front desk do any sales.. just the manager can. But the manager decided to not come in that weekday so thats kind of bummed us out. We could have waited till the bar opened at 12, but with a 11am checkout thats not really an option."

Find out more about Osprey

Search for Vacation rentals in Osprey on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Osprey using one of the methods below:

View our selection of featured Vacation rentals in Osprey
Use the map to find apartments and other Vacation homes in the Osprey neighbourhood you prefer
Enter your travel dates to view the best deals on Vacation rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best vacation rentals in Osprey?

Charming Florida Beach Home w King Bed Patio: Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 31 Expedia vacation rentals, you're sure to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Osprey Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Rentals in Osprey

Charming Florida Beach Home w King Bed Patio

Tropical Beach Resorts

SeaSpray Resort

Hibiscus Suites - Gateway to Siesta Key

The Ringling Beach House

Captiva Beach Resort

Tiny House Siesta

Sea Club I Beach Resort

Kon Tiki Inn

Siesta Palms By the Beach

The Residences at Siesta Key Beach by Hyatt Vacation Club

Venice Beach Villas

Bradenton Apartments by Landing

Siesta Key Island Rentals

The Inn On Siesta Key

Tropical Villas of Venice Beach

Siesta Heron Suites & Villas

Chadwick Cove Resort & Marina

Casey Key Resort - Gulf Shores

Longboat Bay Club

Top Osprey Hotel Reviews

Carlisle Inn

Kompose Boutique Hotel

The Westin Sarasota

Tropical Beach Resorts

Siesta Key Beach Resort and Suites

Spark by Hilton Sarasota Siesta Key Gateway

Lido Beach Resort

Golden Host Resort - Sarasota

Embassy Suites by Hilton Sarasota, FL

Find out more about Osprey

Frequently asked questions