Southwest Florida Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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

5/5(1 area review)

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

Top hotels in Southwest Florida

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 S$298 per night from 3 Aug to 4 Aug
S$298
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (4,756 reviews)
"Beautiful! Amazing!"

Reviewed on 11 Jul, 2025

Tropical Beach Resorts
Naples Grande Beach Resort
Naples Grande Beach Resort
4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
The price is S$259 per night from 10 Aug to 11 Aug
S$259
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,578 reviews)
"Excellent"

Reviewed on 10 Jul, 2025

Naples Grande Beach Resort
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$327 per night from 15 Jul to 16 Jul
S$327
15 Jul - 16 Jul
includes taxes & fees
8.6/10 Excellent! (1,040 reviews)
"Everything excellent"

Reviewed on 13 Jul, 2025

Lani Kai Beachfront Resort
See all 43,244 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

4.5/5(23 reviews)

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

3.5/5(2 reviews)

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$65
per adult
94% 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$141
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
BEST Fort Lauderdale Beach&Lion Country Safari&Palm Beach Day Tour from MIA

Fort Lauderdale & Palm Beach Day Tour from Miami,FL

S$142
per adult
100% of travellers recommend
Fort Lauderdale & Palm Beach Day Tour from Miami,FL
See all activities in Southwest Florida

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.

* 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.