Southwest Florida Beach Vacations
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Top Beach vacation packages in Southwest Florida
- voco Sarasota by IHG
Oct 2 - Oct 6voco Sarasota by IHG + Flight
Central Sarasota4 nights3.5 star property9.0/10 - Wonderful (1,001 reviews)Roundtrip • New York (EWR) - Tampa (TPA)EWR - SRQ • Nonstop SRQ - EWR • Nonstop$665$484found 2 days agoper traveler - LaPlaya Beach & Golf Resort - A Noble House Resort
Sep 25 - Sep 28LaPlaya Beach & Golf Resort - A Noble House Resort + Flight
Vanderbilt Beach3 nights4.5 star property9.0/10 - Wonderful (1,002 reviews)"Excelent"Reviewed July 24, 2026Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • 1 stop RSW - BOS • 1 stop - Cedar Cove Resort and Cottages
Sep 25 - Sep 28Cedar Cove Resort and Cottages + Flight
Holmes Beach3 nights3.0 star property9.2/10 - Wonderful (562 reviews)"The staff was excellent! Our accommodations were very nice, very clean and well maintained. Everything we needed was right at our fingertips during our entire stay."Reviewed July 23, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • 1 stop - The Perry Hotel Naples
Oct 2 - Oct 5The Perry Hotel Naples + Flight
Naples3 nights4.5 star property9.6/10 - Exceptional (965 reviews)"We were early and was able to check in. They front desk employee was very pleasant and made sure we had a room with a good view, since we were celebrating a special birthday. We felt special and were very pleased with our experience. "Reviewed July 24, 2026Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • 1 stop RSW - BOS • 1 stop - The Westin Sarasota
Oct 2 - Oct 6The Westin Sarasota + Flight
Central Sarasota4 nights4.0 star property9.0/10 - Wonderful (1,159 reviews)"Excellent location and hotel."Reviewed July 25, 2026Roundtrip • New York (EWR) - Tampa (TPA)EWR - SRQ • Nonstop SRQ - EWR • Nonstop$800$579found 2 days agoper traveler
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
TownePlace Suites by Marriott Fort Myers Estero
TownePlace Suites by Marriott Fort Myers Estero
Hyatt Place Fort Myers Estero
Hyatt Place Fort Myers Estero
La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.
La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.
Latitude 26 Waterfront Boutique Resort - Bonita Springs
Latitude 26 Waterfront Boutique Resort - Bonita Springs
Hampton Inn & Suites Naples South
Hampton Inn & Suites Naples South
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 $484. 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.)