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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.
Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Price was $608, price is now $574 per person
$574
per person
Jan 25 - Jan 29
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this hotel in Nokomis. Enjoy free WiFi, a marina, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Nokomis Beach and Venice Beach are located nearby.
We loved our 4 night stay at Escape resort, Casey Key. The staff were so helpful and very responsive to any messages I sent before our stay. We will be back ❤️

Reviewed on Oct 29, 2026

Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $1,305, price is now $858 per person
$858
per person
Jan 16 - Jan 23
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this luxury aparthotel in Palmetto. Enjoy free WiFi, free parking, and 2 outdoor pickleball courts. Popular attractions Moccasin Wallow Golf Club and Andersen Race Park are located nearby.

Landing Beautiful 2bd, Gym

Landing Beautiful 2bd, Gym

3 out of 5
Price was $1,049, price is now $761 per person
$761
per person
Dec 19 - Dec 24
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Sarasota (SRQ)
Stay at this apartment in Palmetto. Enjoy free parking, an outdoor pool, and a 24-hour fitness center. Popular attractions Palmetto Historical Park and Manatee County Agricultural Museum are located nearby.

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

2.5 out of 5
Price was $840, price is now $693 per person
$693
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Nokomis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Nokomis Beach and Venice Beach are located nearby.

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was $693, price is now $577 per person
$577
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
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 attractions Nokomis Beach and Turtle Beach are located nearby.

Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was $1,437, price is now $1,304 per person
$1,304
per person
Jan 25 - Jan 29
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this beach hotel in Nokomis. Enjoy free WiFi, free parking, and a private beach. Popular attractions Nokomis Beach and Venice Beach are located nearby.
Nice beach property. Nearby activities and local dining. Quiet area. Needs a littl exterminating for small room pests.

Reviewed on Oct 30, 2026

Home2 Suites by Hilton Nokomis Sarasota Casey Key

Home2 Suites by Hilton Nokomis Sarasota Casey Key

3 out of 5
Price was $668, price is now $614 per person
$614
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Nokomis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Nokomis Beach and Venice Beach are located nearby.
Clean room , clean towels, good breakfast, and very nice friendly staff

Reviewed on Oct 29, 2026

Palmetto Marriott Resort & Spa

Palmetto Marriott Resort & Spa

4.5 out of 5
Price was $1,327, price is now $1,238 per person
$1,238
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Book a stay at this luxury hotel in Palmetto. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Popular attractions Palmetto Historical Park and Manatee County Agricultural Museum are located nearby.
Everything was excellent. No complaints after 3 separate stays here.

Reviewed on Oct 31, 2026

Osprey Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was $491, price is now $431 per person
$431
per person
Jan 25 - Jan 29
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $996, price is now $768 per person
$768
per person
Jan 2 - Jan 6
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

2.5 out of 5
Price was $555, price is now $491 per person
$491
per person
Jan 25 - Jan 29
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was $1,437, price is now $1,304 per person
$1,304
per person
Jan 25 - Jan 29
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

Osprey Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was $693, price is now $577 per person
$577
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $1,305, price is now $858 per person
$858
per person
Jan 16 - Jan 23
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Landing Beautiful 2bd, Gym

Landing Beautiful 2bd, Gym

3 out of 5
Price was $1,049, price is now $761 per person
$761
per person
Dec 19 - Dec 24
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Sarasota (SRQ)
Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

2.5 out of 5
Price was $840, price is now $693 per person
$693
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)

Top Flight Deals

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

Delta
Wed, Jan 20 - Sat, Jan 23
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Jan 20 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Sat, Jan 23, priced at $199 found 3 hours ago
Delta
Tue, Jan 19 - Tue, Feb 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 19 from LaGuardia to Sarasota-Bradenton Intl., returning Tue, Feb 2, priced at $199 found 1 day ago
Delta
Tue, Jan 5 - Sat, Jan 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 5 from Logan Intl. to Sarasota-Bradenton Intl., returning Sat, Jan 9, priced at $209 found 1 hour ago
Southwest Airlines
Tue, Dec 1 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$251 Roundtrip, just found
$251
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Dec 1 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Sat, Dec 5, priced at $251 just found