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.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Price was $1,377, price is now $664 per person
$664
per person
Dec 2 - Dec 9
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,562 reviews)
Very clean hotel, very nice and helpful staff, great food, amazing view. Overall 10/10 experience.
Reviewed on Oct 18, 2025
Bahama Beach Club Pompano
Price was $1,291, price is now $628 per person
$628
per person
Jan 1 - Jan 8
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (13 reviews)
Such a cute property with lots of charm and a great pool. We loved being able to walk to absolutely everything! The owners were so helpful in guiding us in things to do and how to best get around. We can’t wait to return.
Reviewed on Oct 15, 2025
Don't see what you're looking for?
See all available trips from Singapore 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
4.5/5(1,425 reviews)
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
4.5/5(1,225 reviews)
Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.
Venice Beach
4.5/5(862 reviews)
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
$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
Naples Grande Beach Resort
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
Lani Kai Beachfront Resort
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
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.
