Rent Osprey Condos

Start date: Check-in selected.
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Condo Rentals in Osprey

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
6772 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in ...
Captiva Beach Resort
Venice Beach Villas

Venice Beach Villas

3 out of 5
501 W Venice Ave, Venice, FL
Stay at this 3-star business-friendly condo in Venice. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the ...
Venice Beach Villas
Paradise 🏝Beach heaven 🌞condo 🦩<br>

Paradise 🏝Beach heaven 🌞condo 🦩<br>

Englewood
Stay at this condo in Englewood. Enjoy free WiFi, laundry facilities, and tennis courts. Popular attractions Englewood Beach and Englewood South Inlet are located ...
Paradise 🏝Beach heaven 🌞condo 🦩<br>
Save an average of 15% on thousands of hotels when you're signed in
Palm Bay Club Private Balcony Beach Side

Palm Bay Club Private Balcony Beach Side

2 out of 5
Sarasota
Stay at this condo in Siesta Key. Enjoy a beach locale, a fitness center, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located ...
Palm Bay Club Private Balcony Beach Side
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

Siesta Key
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Siesta Key Beach and Lido Beach are located ...
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4 out of 5
1825 Gulf Blvd, Englewood, FL
The price is NZ$922 per night from 10 Sept to 11 Sept
NZ$922
10 Sept - 11 Sept
includes taxes & fees
Stay at this 4-star beach condo in Englewood. Enjoy free WiFi, free parking, and 7 restaurants. Popular attractions Englewood Beach and Lemon Bay are located ...
Chadwick Cove Resort & Marina
Oceanfront/Beachfront -Sarasota Surf  Racquet - Y Building

Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

Sarasota
Book a stay at this beach condo in Siesta Key. Enjoy a beach locale, a fitness center, and a garden. Our guests praise the pool and the helpful staff in our ...
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
Luxury Condo -Breathtaking Front View Beach-PROMO -199 August -Septembe 2025

Luxury Condo -Breathtaking Front View Beach-PROMO -199 August -Septembe 2025

Longboat Key
Book a stay at this beach condo in Longboat Key. Enjoy a beach locale, a water park, and laundry facilities. Our guests praise the helpful staff in our reviews. ...
Luxury Condo -Breathtaking Front View Beach-PROMO -199 August -Septembe 2025
ON Siesta Key BEACH! Pool,Remodeled! 2bd2ba, sleeps 6, 3mins from door to sand

ON Siesta Key BEACH! Pool,Remodeled! 2bd2ba, sleeps 6, 3mins from door to sand

Sarasota
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Siesta Key Beach and Lido Beach are located ...
ON Siesta Key BEACH! Pool,Remodeled! 2bd2ba, sleeps 6, 3mins from door to sand
Don't see what you're looking for?
See all available properties in Osprey
View all properties
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
3739 Condo Rentals
Lowest Price
NZ$306
Highest Price
NZ$922
Popular accommodation
Captiva Beach Resort, Venice Beach Villas, Paradise 🏝Beach heaven 🌞condo 🦩
, Palm Bay Club Private Balcony Beach Side , 1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets, Chadwick Cove Resort & Marina, Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building, Luxury Condo -Breathtaking Front View Beach-PROMO -199 August -Septembe 2025, ON Siesta Key BEACH! Pool,Remodeled! 2bd2ba, sleeps 6, 3mins from door to sand

Top trending hotels in Osprey

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

2.5 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
Stay at this hotel in Osprey. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular ...
Casey Key Resorts - Mainland
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$306 per night from 8 Sept to 9 Sept
NZ$306
8 Sept - 9 Sept
includes taxes & fees
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff ...
Tropical Beach Resorts
Save an average of 15% on thousands of hotels when you're signed in
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
Fully refundableReserve now, pay when you stay
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
Tropical Breeze Resort
Don't see what you're looking for?
See all available properties in Osprey
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.