Southwest Florida Holidays

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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
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South End

If you're spending some time in South End, Winterberry Beach and South Marco Beach are top sights worth seeing.

Find hotels in South End

Top hotels in Southwest Florida

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (4,387 reviews)
"The staff Julio and Ishak are very welcoming and recommended us great restaurants."

Reviewed on 22 Sept, 2025

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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
The price is S$184 per night from 29 Sept to 30 Sept
S$184
29 Sept - 30 Sept
includes taxes & fees
8.6/10 Excellent! (1,023 reviews)
"The area is still recovering from hurricane Ian. Most places are still rebuilding. Lani Kai has come along way still has the fantastic beach nice rooms good food can't wait until the roof top bar and restaurant opens their getting close. Hopefully on our next stay. Our get-away"

Reviewed on 18 Sept, 2025

Lani Kai Beachfront Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is S$262 per night from 30 Sept to 1 Oct
S$262
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (1,486 reviews)
"Great place to stay! You don’t even need to leave the resort if you don’t want to. They have everything. Will definitely be back!"

Reviewed on 22 Sept, 2025

Margaritaville Beach Resort Fort Myers
See all 44,516 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.

Popular places to visit

St. Armands Circle showing a statue or sculpture

St. Armands Circle

Consider this area as a circular outdoor mall. Like any mall, you can shop, dine, browse or just people-watch. Unlike most malls, this one never closes to walkers.

St. Armands Circle

IMG Academy

Enjoy the student vibe when you visit IMG Academy during your travels in Bradenton. Amble around the area's beautiful beaches or attend a sporting event.

IMG Academy

What to do in Southwest Florida

Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

S$66
per adult
92% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

S$142
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
snorkeling

Experience Peanut Island Adventures

S$64
per adult
Experience Peanut Island Adventures
See all activities in Southwest Florida

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 travellers 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 travelling 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.