Southwest Florida Holidays

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    Save up to €185 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Flight + Hotel Deals in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Hilton Cabana Miami Beach Resort

Hilton Cabana Miami Beach Resort

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (292 reviews)
The hotel has potential, but cleanliness definitely needs improvement. Our bathroom had hair stuck to the ceiling of the shower and visible mold in some areas, which was off-putting. Additionally, the parking fees are excessive. Hilton charged $57 + tax for parking, while a lot just two minutes away on foot offered the same service for only $30. For guests already paying a premium to stay here, the parking costs feel unjustified. I’d strongly recommend lowering the price to be more competitive with the surrounding area.

Reviewed on 30 Jul 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!

Reviewed on 31 Jul 2025

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,786 reviews)
Quiet ,clean property. Nice stay

Reviewed on 31 Jul 2025

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,099 reviews)
Everything was good however same breakfast choices everyday.

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
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (6,666 reviews)
Love The Poperty! Just be or

Reviewed on 2 Aug 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! (4,233 reviews)
"Wonderful stay every time"

Reviewed on 29 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 €195 per night from 1 Sept to 2 Sept
€195
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (1,631 reviews)
"Staff are very friendly. Food and service were excellent. People at the pool and beach were great also."

Reviewed on 31 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 €210 per night from 16 Aug to 17 Aug
€210
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (1,278 reviews)
"Beautiful sunsets"

Reviewed on 1 Aug 2025

Sunseeker Resort Charlotte Harbor
See all 43,568 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

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
Lido Beach

Lido Beach

Nothing says holiday like spending a lazy day at Lido Beach, a popular beach in Sarasota. Wander the picturesque gardens or discover the area's beautiful sunsets.

Lido Beach
Venice Beach

Venice Beach

If a restful holiday is part of your travel plans, Venice Beach might be the perfect place to visit during your trip to Venice.

Venice Beach

What to do in Southwest Florida

Sun & Sightseeing Hakuna Matata Catamaran Cruise in Palm Beach

Sun & Sightseeing Hakuna Matata Catamaran Cruise in Palm Beach

€44
per adult
92% of travellers recommend
Sun & Sightseeing Hakuna Matata Catamaran Cruise in Palm Beach
Luxury Sunset Catamaran Cruise

Luxury Sunset Catamaran Cruise

€51
per adult
Luxury Sunset Catamaran Cruise
Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

€47
per adult
100% of travellers recommend
Palm Beach: Sightseeing Catamaran 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 €354, 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.