Browse Osprey Condos for Rent
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Featured Condo Rentals in Osprey
Captiva Beach Resort
6772 Sara Sea Circle Siesta Key FL
With a stay at Captiva Beach Resort in Siesta Key (South Village), you'll be within a 5-minute drive of Siesta Key Beach and Crescent Beach.
A Beach Retreat
105 Casey Key Rd Nokomis FL
When you stay at A Beach Retreat in Nokomis, you'll be on the beach, within a 15-minute drive of Venice Beach and Caspersen Beach.
Venice Beach Villas
501 W Venice Ave Venice FL
With a stay at Venice Beach Villas, you'll be centrally located in Venice, a 3-minute drive from Venice Beach and 7 minutes from Caspersen Beach.
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Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG
Bradenton FL
The price is AU$398 per night from 5 Jan to 6 Jan
AU$398
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this condo in Bradenton, you'll be within a 15-minute drive of IMG Academy and Coquina Beach.
Chadwick Cove Resort & Marina
1825 Gulf Blvd Englewood FL
The price is AU$880 per night from 12 Jan to 13 Jan
AU$880
12 Jan - 13 Jan 2026
includes taxes & fees
When you stay at Chadwick Cove Resort & Marina in Englewood, you'll be near the beach, within a 15-minute walk of Englewood Beach and Lemon Bay.
Siesta Key Waterfront Condo, Beachfront, Pool, Sunset View
Sarasota FL
When you stay at this condo in Siesta Key, you'll be on the beach, a 1-minute drive from Turtle Beach and 7 minutes from Siesta Key Beach.
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Siesta Key FL
The price is AU$598 per night from 4 Jan to 5 Jan
AU$598
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this condo in Siesta Key, you'll be near the beach, steps from Siesta Key Beach and a 3-minute drive from Crescent Beach.
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Siesta Key FL
When you stay at this condo in Siesta Key, you'll be on the beach, a 1-minute drive from Siesta Key Beach and 7 minutes from Turtle Beach.
Siesta Key, beach front condo on America's #1 Beach! 2 BR, 2 Bath, Sleeps 6
Siesta Key FL
When you stay at this condo in Siesta Key, you'll be on the beach, a 1-minute drive from Siesta Key Beach and 7 minutes from Crescent Beach.
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.
Osprey Condo Rentals essential information
Accommodation | 3714 Condo Rentals |
|---|---|
Lowest Price | AU$88 |
Highest Price | AU$880 |
Popular accommodation | Captiva Beach Resort, A Beach Retreat, Venice Beach Villas, Bradenton condo short drive from GORGEOUS Anna Maria Island, near IMG, Chadwick Cove Resort & Marina, Siesta Key Waterfront Condo, Beachfront, Pool, Sunset View, Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach, 1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets, Siesta Key, beach front condo on America's #1 Beach! 2 BR, 2 Bath, Sleeps 6 |
Top trending hotels in Osprey
Casey Key Resorts - Mainland
1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
The price is AU$88 per night from 7 Jan to 8 Jan
AU$88
7 Jan - 8 Jan 2026
includes taxes & fees
With a stay at Casey Key Resorts - Mainland in Osprey, you'll be within a 15-minute drive of Siesta Key Beach and Turtle Beach.
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
When you stay at Kompose Boutique Hotel in Sarasota, you'll be near the airport, within a 15-minute drive of St. Armands Circle and Lido Beach.
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
The price is AU$276 per night from 4 Jan to 5 Jan
AU$276
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Siesta Key (South Village), Tropical Beach Resorts is within a 10-minute walk of Siesta Key Marina and Crescent Beach.
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Carlisle Inn
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
The price is AU$332 per night from 19 Jan to 20 Jan
AU$332
19 Jan - 20 Jan 2026
includes taxes & fees
With a stay at Carlisle Inn in Sarasota (Pinecraft), you'll be within a 15-minute drive of St. Armands Circle and Siesta Key Beach.
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.
More ways to explore Osprey
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^Subject to availability and chosen travel dates.