Search Chalets in Osprey from CA $516

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Osprey Chalets

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Enjoy a serene beach experience with access to turquoise waters and comfortable sun loungers.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

9.8 out of 10, Exceptional, (6)
"Great location to beach, food and entertainment. All within walking distance. Unit was like home aeay from home."
The price is CA $664
CA $845 total
includes taxes & fees
Aug 13 - Aug 14
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr
Enjoy a serene beach experience with access to the turquoise waters and expansive sandy shore.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

10.0 out of 10, Exceptional, (5)
"We had a great time at Siesta key and this house was fantastic! Super easy check in/out, very clean, loves the beach chairs and umbrella - great touch!"
The price is CA $1,450
CA $1,837 total
includes taxes & fees
Aug 12 - Aug 13
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr
Relax on the expansive beach with sun loungers and umbrellas, surrounded by turquoise waters.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

10.0 out of 10, Exceptional, (1)
"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!"
The price is CA $1,033
CA $1,302 total
includes taxes & fees
Aug 11 - Aug 12
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr
Enjoy a serene beach experience with calm waters and comfortable sun loungers.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

9.6 out of 10, Exceptional, (5)
"Owner provided all the beach items and the place was clean and well kept."
The price is CA $1,033
CA $1,312 total
includes taxes & fees
Aug 5 - Aug 6
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio
Enjoy a serene beach experience with access to the ocean.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

10.0 out of 10, Exceptional, (2)
"Property was well taken care of. Extras like coffee, shampoo, soaps, laundry, dishwasher, etc. was unexpected and very welcomed. Nice location and walk to beach was key to our stay!"
The price is CA $1,356
CA $1,725 total
includes taxes & fees
Aug 11 - Aug 12
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Enjoy a tranquil beach experience with calm waters and comfortable sun loungers.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

6.0 out of 10, (1)
"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 "
The price is CA $553
CA $704 total
includes taxes & fees
Aug 5 - Aug 6
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Enjoy a tranquil beach experience with access to the calm turquoise waters and comfortable sun loungers.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

8.0 out of 10, Very good, (4)
"Great location"
The price is CA $516
CA $654 total
includes taxes & fees
Aug 11 - Aug 12
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio
Enjoy sunbathing and relaxation on the beach.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

The price is CA $2,301
CA $2,916 total
includes taxes & fees
Sep 1 - Sep 2
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio
Relax on the beach with sun loungers and umbrellas, surrounded by clear waters and a spacious beachfront area.

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

The price is CA $1,180
CA $1,502 total
includes taxes & fees
Aug 5 - Aug 6
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio
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.
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Top Osprey Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Good simple place! Clean and convenient! "
Julia M dos 4-night trip
Posted 13 hours ago
Tropical Beach Resorts