Search Deals onOsprey Vacation Packages
Osprey Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
Save 100% on your flight
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3-star beach resort in Holmes Beach. Enjoy free WiFi, a beach locale, and free bicycles on site. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Coquina Beach and Bean Point Beach are located nearby.
Captiva Beach Resort
Save 100% on your flight
per person
Oct 2 - Oct 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.
Legacy Hotel at IMG Academy
Save 100% on your flight
per person
Sep 24 - Sep 28
found 7 hours ago
Roundtrip flight included
Nashville (BNA) 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 Smugglers Cove Adventure Golf are located nearby.
Last Hoorah
Save 100% on your flight
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach houseboat in Bradenton. Enjoy free parking, a beach locale, and a picnic area. Popular attractions Coquina Beach and Anna Maria Beach are located nearby.
Tropical Breeze Resort
Save 100% on your flight
per person
Oct 2 - Oct 8
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 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Twin Palms at Siesta
Save 100% on your flight
per person
Nov 1 - Nov 8
found 16 hours ago
Roundtrip flight included
Nashville (BNA) 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.
Tropical Beach Resorts
Save 100% on your flight
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 in our reviews. Popular attractions Siesta Key Beach and Lido 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.
Tue, Oct 28 - Tue, Nov 4
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$107 Roundtrip, found 16 hours ago
$107
Roundtrip
found 16 hours ago
Mon, Nov 3 - Thu, Nov 6
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Tue, Sep 23 - Tue, Sep 30
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$149 Roundtrip, found 2 days ago
$149
Roundtrip
found 2 days ago
Sat, Nov 1 - Wed, Nov 5
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
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