Southwest Florida Vacation Packages

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Your Southwest Florida Vacation

Set off on your next big adventure with a Southwest Florida vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize your escape, you know it'll be one to remember. Begin your trip to Southwest Florida with a couple of days in Tampa visiting popular attractions like Busch Gardens Tampa Bay and Raymond James Stadium. Sarasota is another top city that lures crowds from near and far. Bay Island and Siesta Key Beach are two of the leading places to see here. From the moment you book your Southwest Florida vacation to the second you come back home, Expedia has you covered each step of the way.

Top Southwest Florida Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
Sep 23 - Sep 30
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (136 reviews)
Room was not fully equipped and bathroom was not clean

Reviewed on Aug. 1, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
per person
Oct 16 - Oct 20
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.4/10 Very Good! (36 reviews)
Friendly and kind staff. (that was the highlight) Nice room. Great location.

Reviewed on Jul. 26, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (518 reviews)
A very clean hotel. Well worth the money for that fact alone.

Reviewed on Jul. 28, 2025

Palm House Hotel Palm Beach

Palm House Hotel Palm Beach

4.5 out of 5
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Lauderdale (FLL)
9/10 Wonderful! (63 reviews)
Great hotel, free yoga, hotel car, beach chairs and access. Great service!

Reviewed on Jul. 28, 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

Ready to book your vacation to Southwest Florida?

 

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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
The price is CA $88 per night from Aug 6 to Aug 7
CA $88
CA $116 total
Aug 6 - Aug 7
includes taxes & fees
9/10 Wonderful! (4,204 reviews)
"I spent 2 nights here with my best friend for a birthday getaway and it exceeded our expectations. Every aspect of our stay was a 10 +! The front desk & housekeeping were all smiles at every interaction! Would most definitely recommend and I would stay there again if I am back in the area."

Reviewed on Jul. 30, 2025

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 CA $226 per night from Sep 1 to Sep 2
CA $226
CA $313 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,625 reviews)
"Beautiful hotel with amazing staff!"

Reviewed on Jul. 29, 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 CA $189 per night from Aug 23 to Aug 24
CA $189
CA $272 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (1,278 reviews)
"We love the facilities, the only issue was overcrowding at the pool and other areas of the hotel once it was open to the public on July 4th."

Reviewed on Aug. 1, 2025

Sunseeker Resort Charlotte Harbor
See all 43,411 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Southwest Florida

Siesta Key Beach

Siesta Key Beach

4.5/5(75 reviews)

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

4.5/5(46 reviews)

Nothing says vacation 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

4.5/5(31 reviews)

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

Venice Beach

What to do in Southwest Florida

Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

CA $70
per adult
92% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

CA $74
per adult
100% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Flamingle Happy Hour Cruise

Flamingle Happy Hour Cruise

CA $55
per adult
Flamingle Happy Hour Cruise
See all activities in Southwest Florida

Frequently asked questions

How much does a Southwest Florida vacation package cost?
Less than you might think — from just CA $807, in fact! By bundling flights, hotels and car rentals into your own custom-built vacation 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 vacation 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 travelers.
How far in advance should I book my Southwest Florida vacation?
Get rewarded with the widest variety at the cheapest prices by booking your vacation 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 vacation!
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 vacation 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 vacation is only a couple of clicks away.
Can I choose my airline with a Southwest Florida Expedia vacation 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 vacation 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 vacation 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.

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.