Southwest Florida Vacation Packages

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  • Better together

    Save up to CA $4,200 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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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

Sunshine Beach
Save 100% on your flight
CA $1,696
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
CA $31,030
per person
Dec 28 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Brickell Arch Apartment City Views & Free Parking by Palermo Home Miami

Brickell Arch Apartment City Views & Free Parking by Palermo Home Miami

Brickell
Save 100% on your flight
CA $2,387
per person
Dec 25 - Jan 1
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
10/10 Exceptional! (4 reviews)
The room was very clean and organized with a wonderful city view. The building was relatively quiet. We especially loved how spacious the bathroom area is. Valet and concierge services are exceptional, the restaurant on the 25th floor is great, and it's in a great location in Miami. However, we did encounter one issue that did cost us a decent amount of money. The water connection for the washer was not hooked up and no dryer was available. This meant instead of being able to do our laundry, we had to buy new clothing items. There was also a feminine hygiene wrapper under the bed upon arrival. These things made me question if the bed sheets or towels were properly laundered. Overall, we enjoyed the experience. We typically stay at the Icon, but due to the construction on that building we chose to try the Arch and will probably do that again.

Reviewed on Jul 6, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

Mid Beach
Save 100% on your flight
CA $1,802
per person
Nov 11 - Nov 17
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very good! (1,193 reviews)
I loved the property, the breakfast buffet was on point. The room was so so....it just didn't match what you walked into when you entered the hotel. We caught the bus a lot....the stop was right out front...and the free trolley into south beach was out front. The staff was amazing. They need to put microwaves in the room. We had food and couldn't heat it up...so we ended up throwing it away. Other then that Miami doesn't owe us nothing....we would stay there again.

Reviewed on Oct 5, 2026

1 Hotel South Beach

1 Hotel South Beach

South Beach
Save 100% on your flight
CA $5,357
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,654 reviews)
excellent staff and professional service.. loved the decoration!!

Reviewed on Oct 5, 2026

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
A clear turquoise sea, a sandy beach, and a rocky outcrop with palm trees.

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.

A coastal cityscape with high-rise buildings, palm trees, and a clear blue sky.

South End

While visiting South End, you might make a stop by sights like South Marco Beach and Marco Island Ski & Watersports.

A sandy beach path with people walking, a wooden fence, and a clear blue sky with clouds.

Lido Key

Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.

A person carrying a child on their shoulders on a bridge with a view of greenery and a clear sky.

Central Naples

If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.

A wooden pier extending into calm waters at dusk, with two illuminated structures at the end.

East Naples

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

Ready to book your vacation to Southwest Florida?

Choose your dates

Southwest Florida Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
CA $48
CA $85 total
Oct 13 - Oct 14
includes taxes & fees
Kompose Boutique Hotel
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
CA $192
CA $258 total
Nov 1 - Nov 2
includes taxes & fees
Compass Hotel by Margaritaville Anna Maria Sound
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
CA $235
CA $334 total
Oct 27 - Oct 28
includes taxes & fees
9/10 Wonderful! (2,630 reviews)
"It was a quick trip for us. Room was clean, staff was helpful, pool was great, and the beach was perfect"

Reviewed on Oct 5, 2026

Margaritaville Beach Resort Fort Myers
See all 47,100 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.

Stay near popular Southwest Florida attractions

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 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.
See properties
A beach with lifeguard towers, clear turquoise water, and people sunbathing.

Lido Beach

9.4/10 (6,329 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.
See properties
An aerial view of a city intersection with a central green space surrounded by roads and buildings.

St. Armands Circle

9.4/10 (5,556 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.
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A beach with white sand, turquoise water, and a rocky area in the foreground. There are palm trees and a building in the background.

Naples Beach

9.4/10 (6,040 reviews)
Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.
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A beach with a lifeguard tower, a parked car, and people relaxing under umbrellas.

Venice Beach

9.2/10 (2,687 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.
See properties
A beach with palm trees, a clear blue sky, and a building complex in the background.

Vanderbilt Beach

9.2/10 (2,388 reviews)
If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.
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A bustling street with palm trees, a yellow building, and people walking.

Fifth Avenue South

9.4/10 (2,799 reviews)
Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.
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The Mall at the University Town Center with a modern building, palm trees, and a clear sky.

Mall at University Town Center

9.0/10 (2,156 reviews)
You can search for that perfect souvenir at Mall at University Town Center during your visit to Sarasota. Attend a sporting event or discover the beautiful sunsets in this family-friendly area.
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What to do in Southwest Florida

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

CA $85
per adult
92% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Craft Beer and Wine Sunset Cruise in Palm Beach

Craft Beer and Wine Sunset Cruise in Palm Beach

CA $83
per adult
100% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
Palm Beach: Floatilla Party Cruise

Palm Beach: Floatilla Party Cruise

CA $144
per adult
Palm Beach: Floatilla Party 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 $1,696, 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.

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