Southwest Florida Vacations from $494
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Your Southwest Florida Vacation
Set off on your next big adventure with a Southwest Florida vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize your escape, you know it'll be one to remember. Begin your trip to Southwest Florida with a couple of days in Tampa visiting popular attractions like Busch Gardens Tampa Bay and Raymond James Stadium. Sarasota is another top city that lures crowds from near and far. Bay Island and Siesta Key Beach are two of the leading places to see here. From the moment you book your Southwest Florida vacation to the second you come back home, Expedia has you covered each step of the way.
The Latest Southwest Florida vacation packages
Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites
Save 100% on your flight
Price was $937, price is now $494 per person
$494
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.
Reviewed on May 12, 2025
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See all available trips from San Antonio to Southwest Florida
View all tripsWhere to stay in Southwest Florida
Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida
South End
While visiting South End, you might make a stop by sights like Winterberry Beach and South Marco Beach.
Discover the most popular places to visit in Southwest Florida
Siesta Key Beach
The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.
Lido Beach
Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.
Venice Beach
Beachside bliss awaits at a Florida coastal gem where you can swim, fish and hunt for ancient fossils in the sand and beneath the waves.
What to do in Southwest Florida
2 1⁄2 - Hour Guided Snorkel Tour of Phil Foster Park, Free Videos!
$44
per adult
Palm Beach: Sightseeing Catamaran Cruise
$54
per adult
100% of travellers recommend
Southwest Florida Hotel Deals
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $64 total per night from Oct 7 to Oct 8
$64 total
Oct 7 - Oct 8
Total with taxes and fees
9/10 Wonderful! (4,408 reviews)
"Excellent!"
Reviewed on Oct 5, 2025
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $215 total per night from Oct 12 to Oct 13
$215 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,017 reviews)
"Nice hotel and area.. beach was not that great.. water was orange and brown"
Reviewed on Oct 5, 2025
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
$224 nightly
The price is $250 total per night from Oct 8 to Oct 9
$250 total
Oct 8 - Oct 9
Total with taxes and fees
8.8/10 Excellent! (1,508 reviews)
"Excellent , I recommended 100%"
Reviewed on Sep 30, 2025
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.
Southwest Florida Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tampa Intl. Airport (TPA) |
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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.