Search Deals onOsprey Vacation Packages
Osprey Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Venice Beach Villas
Save 100% on your flight
per person
Jul 14 - Jul 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 property condition in our reviews. Popular attractions Venice Beach and Nokomis Beach are located nearby.
Cedar Cove Resort and Cottages
Save 100% on your flight
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Bradenton Beach and Cortez Beach are located nearby.
Captiva Beach Resort
Save 100% on your flight
per person
Jul 7 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Turtle Beach Resort
Save 100% on your flight
per person
Jul 7 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this hotel in Siesta Key. Enjoy free WiFi, a marina, and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Siesta Key Beach and Turtle Beach are located nearby.
Twin Palms at Siesta
Save 100% on your flight
per person
Jul 7 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Pelican Post at Anna Maria Island Inn
Save 100% on your flight
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Stay at this 3-star apartment in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cortez Beach and Coquina Beach are located nearby.
The Capri at Siesta
Save 100% on your flight
per person
Jul 7 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Legacy Hotel at IMG Academy
Save 100% on your flight
per person
Jul 7 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 4-star golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Coquina Beach and John and Mable Ringling Museum of Art are located nearby.
Osprey Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Osprey Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Jun 17 - Wed, Jun 25
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Wed, Jun 11 - Mon, Jun 16
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$180 Roundtrip, found 14 hours ago
$180
Roundtrip
found 14 hours ago
Tue, May 13 - Sat, May 17
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Thu, May 15 - Fri, May 23
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Oscar Scherer State Park Vacations
- The Oaks Club Vacations
- Historic Spanish Point Vacations
- Nancy's Consignments Vacations
- Siesta Key Beach Vacations
- Lido Beach Vacations
- St. Armands Circle Vacations
- Venice Beach Vacations
- IMG Academy Vacations
- Mall at University Town Center Vacations
- Turtle Beach Vacations
- Nokomis Beach Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Osprey
- Car rentals in Siesta Key
- Car rentals in Sarasota
- Car rentals in Bradenton
- Car rentals in Longboat Key
- Car rentals in Venice
- Car rentals in Englewood
- Car rentals in Port Charlotte
- Car rentals in Nokomis
- Car rentals in Manasota Key
- Car rentals in Lido Key
- Car rentals in North Port
- Car rentals in Lakewood Ranch