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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.
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 $587, price is now $532 per person
$532
per person
Dec 6 - Dec 11
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.

Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $931, price is now $686 per person
$686
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip 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.
The apartment had everything we needed. The bathroom vanity was a pedestal sink with no counter space for toiletries.

Reviewed on Oct 12, 2026

Palmetto Marriott Resort & Spa

Palmetto Marriott Resort & Spa

4.5 out of 5
Price was $731, price is now $656 per person
$656
per person
Dec 6 - Dec 11
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.

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 hour 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

Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Price was $876, price is now $816 per person
$816
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was $626, price is now $588 per person
$588
per person
Dec 6 - Dec 11
found 1 day 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.
Location, right next to the beach

Reviewed on Oct 28, 2026

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was $728, price is now $694 per person
$694
per person
Dec 22 - Dec 26
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.
I received excellent customer service at Casey Key Resorts. They truly care about their guests. When I checked in, I was greeted by Nan. She was very accommodating to my room request. The next day, I had another request and spoke with Nicole at the front desk. She provided me with exceptional customer service to ensure that I had a very comfortable and peaceful staycation. Thank you!😊💜

Reviewed on Oct 27, 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 $530, price is now $479 per person
$479
per person
Jan 15 - Jan 18
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $931, price is now $686 per person
$686
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was $858, price is now $744 per person
$744
per person
Jan 15 - Jan 18
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Price was $734, price is now $658 per person
$658
per person
Jan 15 - Jan 18
found 9 hours ago
Roundtrip non-stop 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 hour ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $1,301, price is now $837 per person
$837
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 hour ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Palmetto Marriott Resort & Spa

Palmetto Marriott Resort & Spa

4.5 out of 5
Price was $731, price is now $656 per person
$656
per person
Dec 6 - Dec 11
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
Sat, Jan 23 - Tue, Jan 26
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 Sat, Jan 23 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Tue, Jan 26, priced at $199 found 3 hours ago
Delta
Tue, Jan 19 - Tue, Feb 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 19 from LaGuardia to Sarasota-Bradenton Intl., returning Tue, Feb 2, priced at $199 found 1 hour ago
Delta
Tue, Jan 5 - Sat, Jan 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Jan 5 from Logan Intl. to Sarasota-Bradenton Intl., returning Sat, Jan 9, priced at $209 found 2 hours ago
American Airlines
Tue, Dec 1 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$229 Roundtrip, found 10 hours ago
$229
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Dec 1 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Sat, Dec 5, priced at $229 found 10 hours ago