Southwest Florida Vacations from ₩985,170

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The Latest Southwest Florida Vacation Packages

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was ₩1,177,442, price is now ₩985,170 per person
₩985,170
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Tampa (TPA)
9.6/10 Exceptional! (1,149 reviews)
Great view, great hotel...close to the beach. Beautiful pool, great bar..highly recommend!

Reviewed on Jun 23, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was ₩1,491,921, price is now ₩1,189,118 per person
₩1,189,118
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Tampa (TPA)
9.6/10 Exceptional! (1,020 reviews)
Our experience was amazing! The staff was helpful with everything we needed, the place was clean and the views were spectacular! Parking was also very convenient. We loved it!

Reviewed on Jun 22, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was ₩1,278,911, price is now ₩1,057,783 per person
₩1,057,783
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Tampa (TPA)
9.2/10 Wonderful! (1,194 reviews)
George and the rest of the staff were absolutely amazing kind courteous welcoming and flexible. They responded very quickly to our communication needs. The location The View the rooms and the pool were all beautiful. Truly one of the best Treasures on the island.

Reviewed on Jun 18, 2026

The Roth Hotel

The Roth Hotel

2 out of 5
Sunset Beach
Price was ₩1,276,318, price is now ₩1,055,956 per person
₩1,055,956
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Tampa (TPA)
10/10 Exceptional! (108 reviews)
Absolutely beautiful property! Very nice docks on the bay and short walk to the beach. Absolutely loved this place. We cannot wait to return.

Reviewed on Jun 22, 2026

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
South Caya Costa and North Captiva Island, panorama, Florida, USA

North Captiva

Visitors to North Captiva enjoy its beaches, and if you want to do some exploring, North Captiva Island Beach is worth a stop.

Find hotels in North Captiva

Find the Best Southwest Florida Vacation Packages

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
The price is ₩86,925 per night from Jun 25 to Jun 26
₩86,925
₩131,220 total
Jun 25 - Jun 26
includes taxes & fees
9.2/10 Wonderful! (5,559 reviews)
"Clean, morden design at an affordable price"

Reviewed on Jun 23, 2026

Kompose Boutique Hotel
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is ₩241,546 per night from Jul 6 to Jul 7
₩241,546
₩347,990 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (2,872 reviews)
"While there were a few standout employees who made our stay more pleasant, including Nicole and Dawn at Half Cracked, Dakota and Alberto at the Front Desk, Ozzy from Electrical, and the housekeeping staff, our overall experience was mixed. The rooms were exceptionally clean and well-maintained throughout ..."

Reviewed on Jun 23, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
The price is ₩259,960 per night from Jun 30 to Jul 1
₩259,960
₩337,171 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (2,277 reviews)
"We stopped by the front desk to let them know that our air conditioner was not working. By the time we got back from dinner, maintenance had already replaced the unit."

Reviewed on Jun 22, 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 46,891 properties in Southwest Florida
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.

Discover the most popular places to visit in Southwest Florida

Siesta Key Beach

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.

Siesta Key Beach
Fifth Avenue South

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
"Anna Maria Island, FL / USA - 11-14-2020: Beautiful sunset at Bean Point Beach in Anna Maria Island."

Bean Point Beach

If a restful vacation is part of your travel plans, Bean Point Beach might be the perfect place to seek out during your trip to Anna Maria. Take in the museums and sunsets in the area.

Bean Point Beach

Frequently asked questions

Can I cancel my flight booking to Southwest Florida due to COVID-19?
Our convenient Customer Service Portal is your one-stop shop for most travel queries, including about flight changes and cancellations related to COVID-19. For greater peace of mind, read through the terms and conditions of your airfare before booking your next flight.
What's the best way to find cheap flights to Southwest Florida that have flexible change policies?
It's as easy as counting 1-2-3 with Expedia. Firstly, enter your preferred dates and destination and click the "Search" button. Step 2: Check "No change fee" just under the "Flexible change policies" heading to the left of your screen. Step 3. Grab your cheap and flexible ticket to Southwest Florida.
What are some of the general tips for travelers to Southwest Florida during the COVID-19 outbreak?
The COVID-19 outbreak has triggered dramatic changes to how we travel. If you plan to visit Southwest Florida, these tips will help you navigate these new challenges and rules:
  • Before booking your flight, find out if any travel bans or restrictions apply — in both your origin and destination. Keep informed with the latest updates by checking official government websites.
  • Requirements state that you must wear a face mask at the airport, including at security checkpoints. Be prepared to adjust your mask to verify your identity when asked by a TSA employee.
  • Instead of handing a TSA officer your boarding pass, position it straight on the reader yourself. When that's done, hold it up for inspection.
  • TSA now permits passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on baggage. This will have to be removed from your bag for screening.
  • Empty your personal items from your pockets, such as your wallet and phone, and place them in your carry-on instead of into bins. This will reduce handling during the screening process.
  • If you're planning to take food on the plane, place it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA officer will need to handle your food container or carry-on bag for inspection.

Which airlines fly to Southwest Florida?
Let Delta get you there. This prominent carrier provides 460 services every month to Southwest Florida Intl. Airport (RSW), a Southwest Florida gateway.
How can I find cheap tickets to Southwest Florida?
In the last seven days, was the lowest price for a flight to Southwest Florida. If you want to save even more, book well ahead of time and be flexible with your dates. Search for your journey to Southwest Florida, then check out prices for similar time frames by clicking on our "flexible dates" link.
How much is a flight to Southwest Florida?
The cost of a round-trip flight to Southwest Florida in the last seven days varied between and . If you were traveling one way from (), you could have landed a cheap fare from only .
What are the most popular airports to fly into in Southwest Florida?
Southwest Florida Intl. Airport (RSW) is the main entryway for those eager to explore Southwest Florida. Roughly 3044 flights every month touch down here.
When is the cheapest time to fly to Southwest Florida?
Jet off on a Tuesday to boost your odds of getting the cheapest fare to Southwest Florida. Mondays are usually the next most affordable day to depart. Saturday is generally the costliest day to fly anywhere.
How much is a plane ticket to Southwest Florida?
In the last seven days, fares to Southwest Florida ranged from to .
Which airlines with flights to Southwest Florida employ COVID-19 cleanliness policies?
In an effort to lessen the contact between passengers and flight crew during the current pandemic, the majority of airlines have taken physical distancing and other strategies to the skies. Just a few of these are:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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.