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

Southwest Florida Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.2/10 Very Good! (1,329 reviews)
Great clean hotel and convenient location but very noisy and AC location blowing directly on bed ….

Reviewed on 23 Jul, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Good stay, hotel was accommodating whenever I needed something. Great location in south beach. Will be back

Reviewed on 20 Jul, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
Amazing place to stay. I will always come back.

Reviewed on 23 Jul, 2025

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.8/10 Excellent! (1,881 reviews)
Easily one of the best properties in miami the view and rooms take your breathe away.

Reviewed on 22 Jul, 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
Loud construction noise is all you hear till 5:00

Reviewed on 22 Jul, 2025

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

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! (4,171 reviews)
"Its the second year that we come back. Very nice hotel. rooms are great, super clean, very comfy beds. Breakfast was included in my booking, but if not I would probably not pay extra. From 2024 to 2025 got skimpy: almost no fruits and the stuff is not really taking care to make sure the food is"

Reviewed on 21 Jul, 2025

Get rates
Kompose Boutique Hotel
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! (1,602 reviews)
"I loved the location of the hotel, the amenities were great. Very beautiful common areas and well kept. The spa was fantastic. The rooms were very spacious, however, somewhat dated for the cost and Star rating of the hotel, but in fairness, they do have a placard that says they’re renovating. Beds ..."

Reviewed on 20 Jul, 2025

Naples Grande Beach Resort
Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is S$288 per night from 2 Aug to 3 Aug
S$288
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,232 reviews)
"Enjoyed our visit."

Reviewed on 22 Jul, 2025

Sunseeker Resort Charlotte Harbor
See all 43,517 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
Flamingle Happy Hour Cruise

Flamingle Happy Hour Cruise

S$52
per adult
Flamingle Happy Hour Cruise
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 S$496, 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.