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.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was CA $2,591, price is now CA $1,472 per person
CA $1,472
per person
Oct 19 - Oct 26
found 10 hours ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.6/10 Exceptional! (598 reviews)
I love it, all staff super nice Beautiful place, clean, awesome beach Thanks

Reviewed on Aug. 24, 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
Price was CA $22,327, price is now CA $11,034 per person
CA $11,034
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Palm House Hotel Palm Beach

Palm House Hotel Palm Beach

4.5 out of 5
Price was CA $3,435, price is now CA $1,924 per person
CA $1,924
per person
Oct 21 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Lauderdale (FLL)
9.2/10 Wonderful! (81 reviews)
We had a wonderful stay! The service was excellent from start to finish—everyone was so attentive and friendly. The beach staff, pool team, and bartenders were all amazing and made our time extra enjoyable. Everything was spotless and well-maintained, and the whole property left a very impressive impression. Highly recommend!

Reviewed on Aug. 26, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was CA $2,897, price is now CA $1,634 per person
CA $1,634
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.8/10 Excellent! (1,193 reviews)
I thoroughly enjoyed my seaside suite. Gorgeous view. Loved that the property is located on the beach. The outdoor beach service is immaculate. John provides wonderful service with a smile. Throughout the property, I found the staff to be kind and attentive. I also enjoyed the pool area and the rooftop spa- it’s small but the service was quality. All in all- I enjoyed my respite at The Pelican.

Reviewed on Aug. 24, 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Price was CA $3,479, price is now CA $1,977 per person
CA $1,977
per person
Nov 4 - Nov 9
found 17 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (73 reviews)
This place is very beautiful, greats views with great customer service. This place just makes you feel very comfortable like your at home

Reviewed on Aug. 20, 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

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
The price is CA $218 per night from Sep 7 to Sep 8
CA $218
CA $311 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,723 reviews)
"Excellent hotel my only issue was the construction noise for renovations but upgrades have to be made so I understand. Also I think they should choose a better brand of soap / conditioner and shampoo the one we had in our room was terrible very bad odor in my opinion I could not use it."

Reviewed on Aug. 23, 2025

Naples Grande Beach Resort
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 CA $193 per night from Sep 1 to Sep 2
CA $193
CA $249 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (4,900 reviews)
"Great value- clean, staff was super responsive, great pool. Our unit had an outdoor private patio which was awesome."

Reviewed on Aug. 24, 2025

Tropical Beach Resorts
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 $211 per night from Sep 1 to Sep 2
CA $211
CA $296 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,395 reviews)
"Great hotel for a Gateway weekend"

Reviewed on Aug. 25, 2025

Sunseeker Resort Charlotte Harbor
See all 43,783 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
Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

CA $151
per adult
96% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
snorkeling

Experience Peanut Island Adventures

CA $69
per adult
Experience Peanut Island Adventures
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 $1,472, 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.