Southwest Florida Beach Vacations
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Top Beach vacation packages in Southwest Florida
- The Perry Hotel Naples
Aug 28 - Aug 30The Perry Hotel Naples + Flight
Naples2 nights4.5 star property9.6/10 - Exceptional (977 reviews)Roundtrip • Philadelphia (PHL) - Fort Myers (RSW)PHL - MIA • Nonstop MIA - PHL • Nonstop$458$333found 7 hours agoper traveler - LaPlaya Beach & Golf Resort - A Noble House Resort
Sep 30 - Oct 3LaPlaya Beach & Golf Resort - A Noble House Resort + Flight
Vanderbilt Beach3 nights4.5 star property9.0/10 - Wonderful (1,013 reviews)Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • 1 stop RSW - BOS • 1 stop - Cedar Cove Resort and Cottages
Oct 6 - Oct 9Cedar Cove Resort and Cottages + Flight
Holmes Beach3 nights3.0 star property9.2/10 - Wonderful (563 reviews)"Everything was amazing from the moment I walked in to the office for check in, the staff was friendly, helpful and informative! This was a home away from home! I will definitely be back next year!"Reviewed July 26, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • 1 stop TPA - BOS • 1 stop - The Westin Sarasota
Oct 6 - Oct 9The Westin Sarasota + Flight
Central Sarasota3 nights4.0 star property9.0/10 - Wonderful (1,143 reviews)Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • 1 stop TPA - BOS • 1 stop$638$475found 1 day agoper traveler - Marco Beach Ocean Suites
Oct 19 - Oct 25Marco Beach Ocean Suites + Flight
South End6 nights2.0 star property8.8/10 - Excellent (1,463 reviews)Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • Nonstop RSW - BOS • 1 stop
Discover the most popular places to visit in Southwest Florida
What to do in Southwest Florida
Palm Beach: Sightseeing Catamaran Cruise
Palm Beach: Floatilla Party Cruise
West Palm Beach Private Boat Cruise and Tour with a Captain
Top Beach Southwest Florida Hotels
Hyatt Place Fort Myers Estero
Hyatt Place Fort Myers Estero
TownePlace Suites by Marriott Fort Myers Estero
TownePlace Suites by Marriott Fort Myers Estero
Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral
Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral
La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.
La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.
Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG
Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG
Baymont by Wyndham Bonita Springs Naples North
Baymont by Wyndham Bonita Springs Naples NorthFind your perfect Southwest Florida beach vacation
How do I book the best Southwest Florida beach vacation packages?
Life’s a beach when you dive into our brilliant Southwest Florida beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.
How can I find cheap beach vacations in Southwest Florida?
A rental steps from the shore creates an amazingly affordable Southwest Florida beach vacation. Seaside sojourns during low season start from $333. Prices and availability are subject to change. Additional terms may apply.
How can I book the best family beach vacations in Southwest Florida?
With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.
How do I find a Southwest Florida beachfront vacation?
Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.
Can I book a package including a Southwest Florida vacation beach house rental?
Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.
Can I find Southwest Florida beach vacation deals?
Sort your search results by deals to delight in amazing Southwest Florida beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.
Can I book a Southwest Florida beach trip with free cancellation and/or flexible dates?
Just like the Southwest Florida tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.
Why should I book my Southwest Florida beach vacation with Expedia?
Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Southwest Florida. (OK, maybe not that last part.)