Osprey Hotels, Resorts, and Rentals

Compare HOTELS, RESORTS, AND RENTALS in Osprey, Florida, USA

Casey Key Resorts - Mainland
FromAU $290 per night
|
8.2 (642 Reviews)
142 Bedrooms 34 Guests
Casey Key Resorts - Mainland
FromAU $272 per night
|
8.8 (1139 Reviews)
1 Bedroom 2 Guests
2-bedroom Spacious townhome in Osprey
10.0 (14 Reviews)
2 Bedrooms 5 Guests
Sand Dollar Retreat
FromAU $254 per night
|
10.0 (1 Review)
2 Bedrooms 6 Guests
🌴 2BR Oasis w/Lanai, Fire Pit + 5 Min to Nokomis Beach
8.0 (2 Reviews)
2 Bedrooms 6 Guests
Modern luxe getaway for families near Siesta Key
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9.0 (3 Reviews)
3 Bedrooms 8 Guests
2BR Florida Home Near the Shore!
6.8 (3 Reviews)
2 Bedrooms 6 Guests
Convenient Cottage Close to Beaches - Pet Friendly!
4.4 (16 Reviews)
2 Bedrooms 5 Guests
Windsor Lodge Unit 3 close to the Beaches Siesta Key
|
9.0 (1 Review)
1 Bedroom 4 Guests
Heated Pool | 3 Beds | Near Beaches and parks
New
3 Bedrooms 6 Guests
Paradise with a pool, pier and private beach area
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8.0 (1 Review)
5 Bedrooms 12 Guests
Charming Florida Beach Home w King Bed Patio
10.0 (2 Reviews)
1 Bedroom 2 Guests
Charming Osprey Home
FromAU $621 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
Relaxing 2BR Florida Home Close to Beach
New
1 Bedroom 2 Guests
Sunny Coastal Escape
FromAU $485 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
Cozy beach bungalow
FromAU $294 per night
10.0 (1 Review)
2 Bedrooms 7 Guests
Villa in Osprey that sleeps the whole family
9.8 (36 Reviews)
2 Bedrooms 5 Guests
A Tropical 2 Bedroom/2 Bath House w/Pool and Dock
9.8 (6 Reviews)
2 Bedrooms 4 Guests
Windsor Lodge Unit 7, studio, close to the beaches, pool access
9.4 (3 Reviews)
1 Bedroom 4 Guests
Windsor Lodge Unit 15, studio, close to the beaches, pool access
9.0 (2 Reviews)
1 Bedroom 4 Guests
COZY BEACH RETREAT JUST MINUTES AWAY FROM BEACH
9.0 (2 Reviews)
2 Bedrooms 4 Guests
Windsor Lodge Unit 3, studio, close to the beaches, pool access
8.8 (3 Reviews)
1 Bedroom 4 Guests
Windsor Lodge Unit #19, studio close to beaches
New
1 Bedroom 4 Guests
Mid-century Waterfront Home with pool
10.0 (38 Reviews)
3 Bedrooms 6 Guests
Rare private beachfront estate on the Gulf.
10.0 (21 Reviews)
5 Bedrooms 8 Guests
Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
10.0 (6 Reviews)
3 Bedrooms 6 Guests
Pet-Friendly Modern Retreat Near Siesta Key
10.0 (5 Reviews)
3 Bedrooms 8 Guests
Sarasota Vacation paradise!
FromAU $485 per night
10.0 (5 Reviews)
3 Bedrooms 8 Guests
Luxury Condo on the water with Intercostal view
10.0 (4 Reviews)
3 Bedrooms 6 Guests
4-bedroom heated pool house 5 minutes to the beach
10.0 (2 Reviews)
4 Bedrooms 12 Guests
Pet Friendly Paradise Close To Sarasota-Venice
9.8 (59 Reviews)
3 Bedrooms 5 Guests
Cozy Cottage in south Sarasota Florida, Close to Beaches!
9.8 (7 Reviews)
3 Bedrooms 6 Guests
Idyllic Casey Key Beach House
FromAU $958 per night
9.6 (36 Reviews)
3 Bedrooms 6 Guests
Huge Pool, Close to Beaches, Restaurants, Shopping & More!
9.6 (30 Reviews)
3 Bedrooms 8 Guests
Paradise with a pool, pier and private beach area
9.0 (22 Reviews)
5 Bedrooms 12 Guests
Royal Luxury Edenville House by Casey Key
New
5 Bedrooms 8 Guests
Luxurious 3/2 Waterfront Retreat in Osprey, FL!
New
3 Bedrooms 5 Guests
New Warm & Cozy Family Home in a Quiet Neighborhood
New
3 Bedrooms 10 Guests
RELAX. ENJOY.
FromAU $146 per night
10.0 (4 Reviews)
3 Bedrooms 6 Guests
Windsor Lodge Unit 10, studio, close to beaches, pool
10.0 (3 Reviews)
1 Bedroom 4 Guests
Pine Run Dog Friendly Condo! Close to beaches!
10.0 (3 Reviews)
3 Bedrooms 3 Guests

About Osprey Vacation Rentals

There are more than 117 places to stay in Osprey that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Osprey.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Osprey, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Osprey. Places to stay near Osprey are 759.7 ft² on average, with prices averaging AU $404 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Osprey with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

Frequently Asked Questions About Osprey?

What are the top hotels or resorts in Osprey?

You have a lot of choices in or near Osprey. If you need a hotel in the Osprey area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Osprey:

How many hotels, resorts, or rentals are available in Osprey?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2026 is over 117 in the Osprey area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Osprey.

Nearby Neighborhood (5)

NeighborhoodProperty Count
Vamo Hotel & Resort Deals in Sarasota, Florida 57
Palmer Ranch Hotel & Resort Deals in Sarasota, Florida 43
Bay Acres Hotel & Resort Deals in Sarasota, Florida 653
Sorrento Shores Hotel & Resort Deals in Sarasota, Florida 555
Rivendell Hotel & Resort Deals in Sarasota, Florida 385