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Compare 8 Chalets in Osprey with updated reviews, rates, and availability.

Living room, with access to the deck, facing west towards the Gulf.

"We loved our stay here! It was an even better location than we had thought, and it made the beach days hassle free. The space was super clean, and we felt much more at ease there than at other Vrbos we have stayed at. Highly recommend! The host was also very accommodating with our early check in. "

Living room with vaulted ceilings and unique artwork

"Very impressive"

SAR 4,649 total

includes taxes & fees

30 Jan - 31 Jan

Living room, with ceiling fan, a/c, and HDTV

"Location was terrific! Beach access was across the street and it was a short walk to restaurants and bars. Great set up for a family stay. "

Dining room with walk-out balcony facing west towards Ocean

"We loved our stay! The rental was clean, had everything we needed, including beach essentials and our host,Kyle, even got us a cooler! But location was the icing on the cake- we could walk to all of the best restaurants as well as a short walk to the beach. Kyle was easy to get in touch with and answered questions in a matter of minutes!"

Queen bed, love seat, a/c, ceiling fan, kitchen, bathroom, HDTV & a private balcony

"Price point was really high for what you get. Small Great location! no ocean view Great communication uncomfortable bed fridge froze some of produce trees overgrown all over electrical wires within inches of the balcony very dangerous unsecure wifi unless reached out to "

Studio with queen bed and third floor balcony with partial ocean views

"We stayed in a cute little studio that had everything we needed! Perfect location, just a short walk to the beach and siesta village! Kyle was a great host and made sure we were taken care of"

Living room, with ceiling fan, a/c, & HDTV

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"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "

SAR 846 total

includes taxes & fees

20 Jan - 21 Jan

"Very lovely (and large!) accommodation. Extremely clean. Front desk staff kind of rude/pretentious.Great location right on the beach at Siesta Key. Heated pool with good poolside bar. Also had a hot tub, which was nice as the weather was a bit cool when we were there. Feel like I was misled a bit based on room description--thought we were booking a room with beach view, but instead got "city view"--which essentially looked into a back alley and at a 7-eleven. For the price/my personal budget,...

SAR 2,266 total

includes taxes & fees

16 Jan - 17 Jan

"Just over the bridge from the Key, stores with in walking distance. Room had a full size refrigerator! Two burner stove pots and pans and local super market not far, no need to eat out every night. The building has been upkept suprisingly very nice , and the staff was very helpful if anything came up. The area is a little older but overall you cant beat the value here. Oh yeah the pool was nice and hey have a grill you can use. "

SAR 632 total

includes taxes & fees

6 Jan - 7 Jan