Southwest Florida Vacations from $336

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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.
Zoo House Down Town Tampa
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
The Retreat Collection at 1 Hotel & Homes South Beach
Bahama Beach Club Pompano
EAST Miami Residences
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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 20 to Oct 21
$81 total
Oct 20 - Oct 21
Total with taxes and fees
9/10 Wonderful! (4,501 reviews)
"The rooms are well maintained & cleaned. The staff is friendly and provides quick check in which is appreciated. Absolutely appreciate the little market for snacks or supplies."

Reviewed on Oct 19, 2025

Kompose Boutique Hotel
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$238 nightly
The price is $265 total per night from Oct 27 to Oct 28
$265 total
Oct 27 - Oct 28
Total with taxes and fees
9/10 Wonderful! (1,868 reviews)
"My family and I had a wonderful stay! The pool and beach were beautiful. We can’t wait to go back."

Reviewed on Oct 18, 2025

Naples Grande Beach Resort
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
$193 nightly
The price is $216 total per night from Oct 20 to Oct 21
$216 total
Oct 20 - Oct 21
Total with taxes and fees
8.8/10 Excellent! (1,054 reviews)
"It’s great place beach is nice food was great the staff at the restaurant on the 1st floor were awesome both lunch and dinner got to meet the manager at dinner and was very impressed with his style he was top notch"

Reviewed on Oct 18, 2025

Lani Kai Beachfront Resort
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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