Osprey showing a bay or harbor and a park

Search Vacation Homes in Osprey

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In one month

In two months

In three months

Vacation Homes in Osprey

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

SAR 1,188 total

includes taxes & fees

30 Sep - 1 Oct

SAR 1,322 total

includes taxes & fees

30 Sep - 1 Oct

"Everything was lovely, just as described. The only problem was the ant problem in the kitchen. "

SAR 1,439 total

includes taxes & fees

30 Sep - 1 Oct

"Had an odor. Property by major roadway. Other than than it was good"

SAR 1,565 total

includes taxes & fees

30 Sep - 1 Oct

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

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

"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"

"Had an awesome with friends and family and will stay again if we’re in the area."

SAR 1,667 total

includes taxes & fees

27 Sep - 28 Sep

SAR 1,132 total

includes taxes & fees

12 Sep - 13 Sep

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. "

"We enjoyed our stay! The place was well-decorated, very clean, & overall comfortable. Hosts were very responsive as well!"

"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."

"Great stay! Nice place and location!"

"Lovely stay at Siesta Key! Minute walk to beaches and restaurants. Very spacious and clean! Highly recommended "

"Very quaint home, it was perfect for us to get away for a birthday weekend and enjoy the beach!"

SAR 1,632 total

includes taxes & fees

25 Sep - 26 Sep

"Stayed 2 nights so we could attend an Orioles Spring Training game. Very nice facility and very nice hosts! "

"Would highly recommend for a one or two night stay"

"The house was renovated beautifully, was clean and filled with lots a little extras. Would love to stay again."

"We enjoyed our stay very much. Will stay again"

SAR 1,431 total

includes taxes & fees

15 Sep - 16 Sep

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

Top Osprey Hotel Reviews

Tropical Beach Resorts

10/10 Excellent

"Loved the beach"

Ameniti Bay, BW Signature Collection

10/10 Excellent

"Property was nice and clean. Enough parking space. Staff very friendly and helpful. I thing I didn’t like was that the fired pit was hitting along with the grill which when I was booking it didn’t mention anything about having a grill, which I would of loved to grill with my kids one of the night I stayed there, but other than that everything went well "