Search Vacation Homes in Osprey

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

28 Rab. I - 30 Rab. I

In two weeks

4 Rab. II - 6 Rab. II

In one month

18 Rab. II - 20 Rab. II

In two months

16 Jum. I - 18 Jum. I

Compare 3679 Vacation Homes in Osprey with updated reviews, rates, and availability.

Beach nearby, beach umbrellas, beach towels

"Perfect location to walk to beach and town. The Villas and grounds were well maintained. I wouldnt hesitate staying hefe again."

"Great place for our short visit for my dad’s 80th birthday! Everyone enjoyed the accommodations and the kids loved the pool. We would have loved to stay longer."

"Terrific property with outstanding host/manager. The best appointed and provisioned property ever leased. Very considerate of vacationers and visitors with all amenities in good repair and staples provided. Outstanding experience."

"Our stay at was absolutely wonderful! From the moment we arrived, we felt right at home. The property is even more beautiful in person than in the photos. The space was clean, spacious, and thoughtfully decorated. We loved the cozy ambiance and all the little touches that made it feel like a true retreat. The backyard is a lush wonderland of gorgeous trees and plants, and is fully fenced, so great for dogs. The location is fantastic – quiet, yet close enough to all the attractions we wanted to...

SAR 2,847 total

includes taxes & fees

19 Apr - 20 Apr

On the beach, sun loungers, beach towels

"Everything was clean & beautiful! Wonderful property manager that reached out to ensure that everything was working properly and we were having a great time! Would definitely stay again!"

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

SAR 1,568 total

includes taxes & fees

31 Mar - 1 Apr

"We had a wonderful stay. This is truly a very short walk to the beach as well as to the Siesta Key restaurants and shops. We truly enjoyed our stay!"

SAR 4,355 total

includes taxes & fees

26 Mar - 27 Mar

Beach nearby, sun loungers, beach towels

"The accommodations were actually better than the description. All new appliances, bedding etc. it was all new. Freshly painted and accessories. 3 minute walk to beach. 3 minute walk to Siesta Village restaurants and bars. Highly recommend. "

"The four of us had a wonderful "Retreat from The Winter" at Miramar! The home, especially the kitchen, was comfortable and well equipped, including many beach chairs. The access to the beach was terrific, with a short walk across the street, through the Aloha Kai gate, and down the private driveway to the white sandy beach. The weather cooperated too, after the one day of rain. The traffic was horrendous, due to a weekday maintenance of the bridge, which was totally out of the hands of the...

"The home was great, it had everything we needed for our stay. "

"A nice big vacation home"

SAR 3,091 total

includes taxes & fees

21 Apr - 22 Apr

"We enjoyed our stay and the owners were super helpful and great. Description was just as advertised and close to everything we needed. Would stay here again. Thank you "

"My family and I came down for a weekend stay and the place was perfect for us (2 adults, 3 children ages 3, 9, 13.) We made great use of the backyard pool and lounge area. The location was great for our needs - allowed us to easily get to Siesta Key and up to Ed Smith Stadium for some O's spring training games. The house was exactly as pictured. Check in and out were very easy. "

"This property is maintained with every consideration in mind. The owners thought of everything - we were very pleased."

"We stayed 2 nights and everything was good. I was Leary booking a vacation from a hotel name for a small condo/ hotel room. This room had 2 queen beds, bathroom and all amenities as a hotel for half the price. Thank you … would recommend this for others that don’t need a high end place. Thanks again"

SAR 647 total

includes taxes & fees

16 Apr - 17 Apr

"Property was "as advertised. Location was excellent for ease of access to Venice and the surrounding area. Bird life was especially good for viewing in the back yard and we had at least 3 small alligators in the lake. Interior of the house was clean but could use some further maintenance (eg not all the blinds are in good repair.). Host was responsive and easy to work with."

"The property was clean and cozy. It had all the things we needed and worked great for the few days we were in Sarasota to visit friends. We hope to stay here again on our next visit. "

"We had a lovely time.. needs to be updated. Area rug was very dirty.. could use some small upgrades. Kitchen well equipped."

SAR 1,973 total

includes taxes & fees

22 Mar - 23 Mar

"Nice property. Owners new to Vrbo with this property and really want to make it great. Good communication. Had a few hiccups with cleanliness as we first got in and pool condition but the owners got right on it to make it right. Neighborhood is fantastic. I do the living room could use some extra seating in the living room for a larger family stay. Maybe a loveseat or another sofa . Pool was nice but note that the whirlpool spa pictured is not working as a spa and is same temp as pool and no...