Southwest Florida Vacations from $384

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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.
Broadmore Miami Beach
The Retreat Collection at 1 Hotel & Homes South Beach
Bahama Beach Club Pompano
The Local House
Flow Miami Hotel
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Where to stay in Southwest Florida

Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida

Discover the most popular places to visit in Southwest Florida

What to do in Southwest Florida

Southwest Florida Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $81 total per night from Oct 16 to Oct 17
$81 total
Oct 16 - Oct 17
Total with taxes and fees
9/10 Wonderful! (4,440 reviews)
"Beautiful hotel especially for the price."

Reviewed on Oct 9, 2025

Kompose Boutique Hotel
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $214 total per night from Oct 21 to Oct 22
$214 total
Oct 21 - Oct 22
Total with taxes and fees
8.8/10 Excellent! (1,033 reviews)
"The thing that i did not like was that the tub was small and we had to pay for parking each day. Everything else was great."

Reviewed on Oct 11, 2025

Lani Kai Beachfront Resort
Inn on Fifth

Inn on Fifth

4 out of 5
699 5th Ave S, Naples, FL
Fully refundable
$241 nightly
The price is $268 total per night from Nov 3 to Nov 4
$268 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"The only downside was that the balcony was small. Everything else was excellent!"

Reviewed on Oct 12, 2025

Inn on Fifth
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.