Southwest Florida Holidays

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Our guide on 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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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

Southwest Florida Holiday

Our pick of the best 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
9/10 Wonderful! (4,360 reviews)
"Great rates, nice room. Only thing was the one elevator working but the stairs were open to the outside so it was ok!"

Reviewed on 15 Sept 2025

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Kompose Boutique Hotel
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundableReserve now, pay when you stay
The price is NZ$423 per night from 28 Sept to 29 Sept
NZ$423
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (1,774 reviews)
"Staff very nice and accommodating"

Reviewed on 15 Sept 2025

Naples Grande Beach Resort
Inn on Fifth

Inn on Fifth

4 out of 5
699 5th Ave S, Naples, FL
Fully refundable
The price is NZ$527 per night from 25 Sept to 26 Sept
NZ$527
25 Sept - 26 Sept
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
Solo vacation
"The hotel is right on 5th avenue south, plenty of shops and restaurants. The staff were great and very accommodating. Jose from valet had great dining recommendations, Israel, Lisa and I believe Judy from the front desk were very helpful and exceptional. Nicole from the spa was amazing and great ..."

Reviewed on 15 Sept 2025

Inn on Fifth
See all 44,269 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
St. Armands Circle which includes 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
5th Avenue Shopping District featuring markets, street scenes and a city

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

What to do in Southwest Florida

Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

NZ$87
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

NZ$186
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
snorkeling

Experience Peanut Island Adventures

NZ$85
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.