Search Deals onOsprey Vacation Packages
Osprey Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Tropical Beach Resorts
Price was $733, price is now $557 per person
$557
per person
May 19 - May 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $1,701, price is now $1,238 per person
$1,238
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
The Residences at Siesta Key Beach by Hyatt Vacation Club
Save 100% on your flight
Price was $2,290, price is now $1,672 per person
$1,672
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach hotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Legacy Hotel at IMG Academy
Price was $791, price is now $580 per person
$580
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and IMG Bollettieri Tennis Academy are located nearby.
Captiva Beach Resort
Save 100% on your flight
Price was $1,000, price is now $745 per person
$745
per person
May 3 - May 8
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.
Bradenton Apartments by Landing
Save 100% on your flight
Price was $1,191, price is now $888 per person
$888
per person
Jun 14 - Jun 19
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this luxury aparthotel in Bradenton. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Coquina Beach and IMG Bollettieri Tennis Academy are located nearby.
Resort Sixty-Six
Save 100% on your flight
Price was $1,485, price is now $1,127 per person
$1,127
per person
May 16 - May 23
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Bradenton Beach and Anna Maria Beach 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.
Sat, Apr 4 - Fri, Apr 24
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$163 Roundtrip, found 4 days ago
$163
Roundtrip
found 4 days ago
Thu, Apr 9 - Fri, Apr 17
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Mon, Apr 27 - Tue, May 12
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$231 Roundtrip, found 4 days ago
$231
Roundtrip
found 4 days ago
Wed, May 13 - Sat, May 16
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$232 Roundtrip, found 11 hours ago
$232
Roundtrip
found 11 hours ago
Discover Other Travel Deals
- Oscar Scherer State Park Vacations
- Historic Spanish Point Vacations
- The Oaks Club Vacations
- Nancy's Consignments Vacations
- Siesta Key Beach Vacations
- Lido Beach Vacations
- St. Armands Circle Vacations
- Venice Beach Vacations
- IMG Academy Vacations
- Turtle Beach Vacations
- Mote Marine Laboratory & Aquarium Vacations
- Mall at University Town Center 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
