Southwest Florida Beach Vacations
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Top Beach vacation packages in Southwest Florida
Price found within the past 48 hours. Click for updated prices.
- voco Sarasota by IHG
Oct 13 - Oct 17voco Sarasota by IHG + Flight
Central Sarasota4 nights3.5 star property9.0/10 - Wonderful (1,001 reviews)Roundtrip • New York (JFK) - Tampa (TPA)JFK - TPA • Nonstop TPA - JFK • Nonstop$753$527found 1 day agoper traveler - LaPlaya Beach & Golf Resort - A Noble House Resort
Oct 6 - Oct 12LaPlaya Beach & Golf Resort - A Noble House Resort + Flight
Vanderbilt Beach6 nights4.5 star property9.0/10 - Wonderful (1,002 reviews)"Excelent"Reviewed July 24, 2026Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • Nonstop RSW - BOS • 1 stop - The Perry Hotel Naples
Oct 6 - Oct 12The Perry Hotel Naples + Flight
Naples6 nights4.5 star property9.6/10 - Exceptional (966 reviews)Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • Nonstop 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 - Legacy Hotel at IMG Academy
Sep 25 - Sep 29Legacy Hotel at IMG Academy + Flight
Bradenton4 nights4.0 star property9.0/10 - Wonderful (1,002 reviews)Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • 1 stop$763$566found 1 day agoper traveler
Discover the most popular places to visit in Southwest Florida
What to do in Southwest Florida
Palm Beach: Sightseeing Catamaran Cruise
$61
per adult
100% of travelers recommend
Palm Beach: Floatilla Party Cruise
$103
per adult
0% of travelers recommend
West Palm Beach Private Boat Cruise and Tour with a Captain
$290
per traveler
0% of travelers recommend
Top Beach Southwest Florida Hotels
Hyatt Place Fort Myers Estero
Hyatt Place Fort Myers Estero3.5 star property
19.4 mi from Southwest Florida
8.8 out of 10, Excellent, (1,001 reviews)
8.8/10
Excellent
(1,001 reviews)
$103 nightly
The price is $115
$115 total
Aug 22 - Aug 23
Total with taxes and fees
9.2 out of 10, Wonderful, (1,792 reviews)
9.2/10
Wonderful
(1,792 reviews)
"Solo el 4 de Julio no había Internet"
$92 nightly
The price is $103
$103 total
Jul 26 - Jul 27
Total with taxes and fees
TownePlace Suites by Marriott Fort Myers Estero
TownePlace Suites by Marriott Fort Myers Estero3.5 star property
19.5 mi from Southwest Florida
9.4 out of 10, Exceptional, (549 reviews)
9.4/10
Exceptional
(549 reviews)
"Love it"
$108 nightly
The price is $121
$121 total
Aug 17 - Aug 18
Total with taxes and fees
9.4 out of 10, Exceptional, (1,312 reviews)
9.4/10
Exceptional
(1,312 reviews)
"This was the perfect stay. I got To Naples a lot because I live in Ft. Lauderdale and this is the only place I will Stay moving forward. Big rooms, pool, breakfast, easy checkin and out and close to everything. Can’t wait to go back. Felt like a little hidden garden hotel in the middle of Naples."
$74 nightly
The price is $83
$83 total
Jul 26 - Jul 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral
Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral3.0 star property
10.8 mi from Southwest Florida
8.8 out of 10, Excellent, (896 reviews)
8.8/10
Excellent
(896 reviews)
"This hotel is in an ideal location to quickly access beaches, shopping, and restaurants. The staff, especially the front desk, were very welcoming and informative about status of the beaches and things to do with the grandkids.The rooms, pool, and entire facility were very clean. The pool was very well maintained and the kids loved it after a day at the beach.The hotel was very cost effective considering a breakfast buffet, free parking, and location.I would definitely stay here again on my...
$79 nightly
The price is $88
$88 total
Aug 1 - Aug 2
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.
La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.3.0 star property
25.1 mi from Southwest Florida
9.0 out of 10, Wonderful, (1,471 reviews)
9.0/10
Wonderful
(1,471 reviews)
$90 nightly
The price is $100
$100 total
Aug 9 - Aug 10
Total with taxes and fees
Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG
Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG2.5 star property
15.8 mi from Southwest Florida
9.2 out of 10, Wonderful, (1,007 reviews)
9.2/10
Wonderful
(1,007 reviews)
"Staff was extremely helpful and kind!"
$83 nightly
The price is $93
$93 total
Jul 29 - Jul 30
Total with taxes and fees
Baymont by Wyndham Bonita Springs Naples North
Baymont by Wyndham Bonita Springs Naples North2.5 star property
24.3 mi from Southwest Florida
8.2 out of 10, Very Good, (1,048 reviews)
8.2/10
Very Good
(1,048 reviews)
"Convenient location. Nice breakfast. Comfortable beds. There should be conditioner in the shower. Ironing board but no iron. Unexpected video check-in procedure."
$78 nightly
The price is $87
$87 total
Jul 29 - Jul 30
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find 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 $527. 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.)