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Osprey Vacation Packages

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Osprey Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $812, price is now $562 per person
$562
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Kansas City (MCI) 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.
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,353, price is now $1,317 per person
$1,317
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Sarasota (SRQ)
Book a stay at this beach hotel in Bradenton Beach. Enjoy a beach locale, daily housekeeping, and cable TV channels. Popular attractions Coquina Beach and Bradenton Beach are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,339, price is now $875 per person
$875
per person
May 9 - May 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,942, price is now $1,373 per person
$1,373
per person
May 11 - May 17
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Sarasota (SRQ)
Stay at this aparthotel in Siesta Key. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Save 100% on your flight
Price was $1,916, price is now $1,366 per person
$1,366
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sarasota (SRQ)
Book a stay at this 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.
Azul Resort Siesta Key

Azul Resort Siesta Key

3 out of 5
Save 100% on your flight
Price was $1,473, price is now $1,055 per person
$1,055
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sarasota (SRQ)
Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,806, price is now $1,319 per person
$1,319
per person
May 9 - May 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Sarasota (SRQ)
Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,078, price is now $795 per person
$795
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) 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 LECOM Park and Longboat Key Beaches are located nearby.

Osprey Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $812, price is now $562 per person
$562
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Sarasota (SRQ)
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,353, price is now $1,317 per person
$1,317
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,339, price is now $875 per person
$875
per person
May 9 - May 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,225, price is now $856 per person
$856
per person
May 9 - May 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Sarasota (SRQ)

Osprey Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Azul Resort Siesta Key

Azul Resort Siesta Key

3 out of 5
South Village
Save 100% on your flight
Price was $1,473, price is now $1,055 per person
$1,055
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sarasota (SRQ)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $2,082, price is now $1,370 per person
$1,370
per person
Apr 16 - Apr 21
found 10 hours ago
Roundtrip flight included
Kansas City (MCI) to Sarasota (SRQ)
SeaSpray Resort

SeaSpray Resort

4 out of 5
Save 100% on your flight
Price was $1,942, price is now $1,373 per person
$1,373
per person
May 11 - May 17
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Sarasota (SRQ)
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Siesta Key Village
Save 100% on your flight
Price was $1,916, price is now $1,366 per person
$1,366
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Sarasota (SRQ)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sun, Apr 12 - Thu, Apr 16
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$160 Roundtrip, just found
$160
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Apr 12 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Thu, Apr 16, priced at $160 just found
Frontier Airlines
Sat, May 2 - Thu, May 7
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$196 Roundtrip, found 4 hours ago
$196
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 2 from LaGuardia to Sarasota-Bradenton Intl., returning Thu, May 7, priced at $196 found 4 hours ago
Frontier Airlines
Thu, Mar 26 - Sat, Mar 28
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$204 Roundtrip, found 6 days ago
$204
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Mar 26 from Philadelphia Intl. to Sarasota-Bradenton Intl., returning Sat, Mar 28, priced at $204 found 6 days ago
United
Wed, May 27 - Tue, Jun 9
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$214 Roundtrip, found 1 day ago
$214
Roundtrip
found 1 day ago
Select United flight, departing Wed, May 27 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Tue, Jun 9, priced at $214 found 1 day ago