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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Siesta Key Village

Siesta Key Village is known for its stunning beaches, and with sights like Siesta Key Beach and Siesta Key Farmers Market, you won't get bored spending a day wandering around this part of Siesta Key.

Find hotels in Siesta Key Village

Southwest Florida Holiday

Our pick of the best Southwest Florida Hotel Deals

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 NZ$422 per night from 3 July to 4 July
NZ$422
3 July - 4 July
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"We had a wonderful stay staff was awesome view was amazing"

Reviewed on 27 Jun. 2025

Lani Kai Beachfront Resort
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 NZ$368 per night from 6 July to 7 July
NZ$368
6 July - 7 July
includes taxes & fees
9.4/10 Exceptional! (1,527 reviews)
"Loved everything about this hotel!"

Reviewed on 29 Jun. 2025

Compass Hotel by Margaritaville Anna Maria Sound
Tropical Beach Resorts
Tropical Beach Resorts
3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$385 per night from 2 July to 3 July
NZ$385
2 July - 3 July
includes taxes & fees
9.2/10 Wonderful! (4,730 reviews)
"We always have a great stay"

Reviewed on 27 Jun. 2025

Tropical Beach Resorts
See all 43,110 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.

Frequently asked questions

How much does a Southwest Florida holiday package cost?
Less than you might think --- from just , in fact! By bundling flights, hotels and car rentals into your own custom-built holiday package, your getaway to Southwest Florida is just a few clicks away.
How do I get a cheap travel package to Southwest Florida?
Browse and book everything in the one place with our Southwest Florida holiday packages. We have incredible bargains on flights, hotels and more that'll keep your pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1 000 000 properties worldwide to select from, you'll have the flexibility to mix and match all you want.
Where should I stay in Southwest Florida?
You can't go past Tampa, with terrific landmarks including Raymond James Stadium and University of South Florida to discover. Or, if sights like Edison and Ford Winter Estates and Sun Splash Water Park are more your scene, Fort Myers is the place for you.
What are the top hotels in Southwest Florida?
Naples Grande Beach Resort and La Quinta Inn & Suites by Wyndham Naples East (I-75) know how to make their guests feel welcome in Naples. If your itinerary also includes Cape Coral, take a look at Trianon Bonita Bay and Sanibel Island Beach Resort. Both are very popular with travellers.
How far in advance should I book my Southwest Florida holiday?
Get rewarded with the widest variety at the cheapest prices by booking your holiday to Southwest Florida nice and early. Air carriers generally advertise tickets around a year before departure, so reserve your spot as soon as possible. That being said, Expedia is dedicated to providing you with the best deals around, so there's never a bad time to book your dream holiday!
What does an Expedia Southwest Florida travel package include?
That mostly depends on you. You can select from a range of Southwest Florida bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Southwest Florida holiday looks like, you're sure to save!
What should I know before booking a Southwest Florida travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next awesome holiday is only a couple of clicks away.
Can I choose my airline with a Southwest Florida Expedia holiday package?
Yes --- that's the beauty of an Expedia package. You're the boss! We have access to more than 550 partner airlines all over the world, so you have options galore when putting together your Southwest Florida escape.
If I'm not able to travel, can I cancel my Southwest Florida holiday package?
It's hard to predict what the future holds, so it's good to know that you can cancel or change your Southwest Florida holiday package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Southwest Florida

Siesta Key Beach

Siesta Key Beach

4/5(1 review)

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

Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

NZ$183
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

NZ$85
per adult
94% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
Flamingle Happy Hour Cruise

Flamingle Happy Hour Cruise

NZ$67
per adult
Flamingle Happy Hour Cruise
See all activities in Southwest Florida
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.