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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Osprey Cottages

Our top choices for Osprey cottages

The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The price is CA $333
CA $452 total
includes taxes & fees
Aug 21 - Aug 22
The Inn On Siesta Key
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Fridge, microwave, oven, stovetop

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

8.0 out of 10, Very good, (1)
"Beautiful decor, perfect location to the beach (5min walking). very thoughtful touches throughout the rental. The kitchen is well- equipped with all you need. Bedroom with excellent mattress. The patio with BBQ, kayaks, free parking, beach chair /loungers available, the property was immaculate.10/10. I would recommend""
The price is CA $276
CA $693 total
includes taxes & fees
Aug 26 - Aug 27
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Sun loungers, beach towels

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (76)
"Its right next to everything we needed"
The price is CA $137
CA $418 total
includes taxes & fees
Aug 27 - Aug 28
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Exterior

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

The price is CA $283
CA $702 total
includes taxes & fees
Aug 26 - Aug 27
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
The price is CA $206
CA $702 total
includes taxes & fees
Aug 24 - Aug 25
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Beach

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

9.8 out of 10, Exceptional, (32)
"Fun stay, great location"
The price is CA $207
CA $340 total
includes taxes & fees
Aug 21 - Aug 22
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (60)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is CA $246
CA $629 total
includes taxes & fees
Aug 24 - Aug 25
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
5 star Guest House heated pool on the water!
Beach

5 star Guest House heated pool on the water!

The price is CA $345
CA $702 total
includes taxes & fees
Aug 23 - Aug 24
5 star Guest House heated pool on the water!
Haven cottage Across street from beach and Heated Pool
Terrace/patio

Haven cottage Across street from beach and Heated Pool

9.8 out of 10, Exceptional, (7)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
The price is CA $368
CA $469 total
includes taxes & fees
Aug 21 - Aug 22
Haven cottage Across street from beach and Heated Pool
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (95)
"We have stayed at this cottage before- just love this beach."
The price is CA $246
CA $593 total
includes taxes & fees
Aug 24 - Aug 25
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Nest Cottage Across street from beach and Heated Pool
Pool

Nest Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (2)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
The price is CA $482
CA $614 total
includes taxes & fees
Aug 23 - Aug 24
Nest Cottage Across street from beach and Heated Pool
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Nice, trendy and clean! Very fancy yet inexpensive!"
Antoinette 3-night trip
Posted 14 hours ago
Kompose Boutique Hotel