Gulf Shores Vacations from $529
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The Latest Gulf Shores Vacation Packages
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- LaPlaya Beach & Golf Resort - A Noble House Resort
Oct 1 - Oct 6LaPlaya Beach & Golf Resort - A Noble House Resort + Flight
Vanderbilt Beach5 nights4.5 star property9.0/10 - Wonderful (1,007 reviews)Roundtrip • Chicago (CHI) - Fort Myers (RSW)ORD - RSW • Nonstop RSW - ORD • Nonstop - A Wave From it All
Sep 7 - Sep 12A Wave From it All + Flight
Siesta Isle5 nights2.0 star propertyRoundtrip • Minneapolis (MSP) - Fort Myers (RSW)MSP - RSW • Nonstop RSW - MSP • 1 stop - Manasota Key Resort
Sep 3 - Sep 7Manasota Key Resort + Flight
Manasota Key4 nights2.5 star property9.4/10 - Exceptional (304 reviews)"We were only on property for 10 minutes before agreeing that we needed to come back every year. It is a little piece of paradise. We used all the things, from lawn chairs to shuffle boards, paddle boards, bikes, and pool. It is a short drive to restaurants and stores, but the kitchenette was perfect for cooking a quick meal. The rooms are spacious and comfortable."Reviewed July 16, 2026Roundtrip • New York (EWR) - Fort Myers (RSW)EWR - RSW • Nonstop RSW - EWR • Nonstop - The Perry Hotel Naples
Oct 1 - Oct 6The Perry Hotel Naples + Flight
Naples5 nights4.5 star property9.6/10 - Exceptional (957 reviews)"Hotel is new and everything was great!"Reviewed July 20, 2026Roundtrip • Chicago (CHI) - Fort Myers (RSW)ORD - RSW • Nonstop RSW - ORD • Nonstop
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.