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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,474, price is now CA $828 per person
CA $828
per person
Mar 31 - Apr 7
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Older property but very well maintained. It was clean and had everything we needed for our stay. Great communication with the host.

Reviewed on Feb 10, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $10,325, price is now CA $4,126 per person
CA $4,126
per person
May 4 - May 10
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (311 reviews)
The sheets had stains on the when we arrived. The room was outdated but for the price we did kind of expect that. I was told we would have to pay extra for any additional sheets however when I told them they had already started out looking dirty they finally gave us new, but that was several nights into the stay. Most staff didn't speak english so there wasn't great communication or friendliness. It was nice to have the pool and beach within walking distance. Windows would open but no screens which was disappointing because if you wanted fresh air there was a fear of birds flying in. We also had a decent leak from our AC unit running down through the drywall causing it to bubble up and pool on the floor which caused me to slip and fall.

Reviewed on Feb 19, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $2,936, price is now CA $1,214 per person
CA $1,214
per person
Apr 22 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Great little hotel! In a really nice location

Reviewed on Feb 17, 2026

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 $28,354, price is now CA $13,436 per person
CA $13,436
per person
Mar 30 - Apr 4
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $2,206, price is now CA $1,184 per person
CA $1,184
per person
Mar 30 - Apr 4
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Great location, clean room and beautiful.

Reviewed on Feb 19, 2026

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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
Siesta Key Village

Siesta Key Village

4.5/5(12 area reviews)

Travelers to Siesta Key Village praise its stunning beaches. If you've got some more time to explore, be sure to make a stop by Siesta Key Beach and Siesta Key Farmers Market.

Find hotels in Siesta Key Village

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 $213 per night from Feb 22 to Feb 23
CA $213
CA $257 total
Feb 22 - Feb 23
includes taxes & fees
9/10 Wonderful! (5,031 reviews)
Convenient location. Room was spotless when we arrived. Would not clean unless requested in advance. Staff was welcoming and friendly.

Reviewed on Feb 18, 2026

Kompose Boutique Hotel
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Mar 10 to Mar 11
CA $210
CA $304 total
Mar 10 - Mar 11
includes taxes & fees
9.2/10 Wonderful! (1,881 reviews)
The room was spotless and the service more than amazing

Reviewed on Feb 20, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is CA $168 per night from Feb 23 to Feb 24
CA $168
CA $190 total
Feb 23 - Feb 24
includes taxes & fees
8.4/10 Very Good! (2,278 reviews)
There was construction happening during my stay so I didn’t get the best experience but with that being said i did have a great time

Reviewed on Feb 15, 2026

Golden Host Resort - Sarasota
See all 46,626 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.
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Beach Vacations
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Discover the most popular places to visit in Southwest Florida

Southwest Florida featuring general coastal views and a beach as well as a large group of people

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 showing general coastal views and a sandy 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
St. Armands Circle showing a statue or sculpture

St. Armands Circle

4.5/5(49 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

What to do in Southwest Florida

Green sea turtle swimming by the snorkel trail

2 1⁄2 - Hour Guided Snorkel Tour of Phil Foster park, Free Videos!

CA $60
per adult
2 1⁄2 - Hour Guided Snorkel Tour of Phil Foster park, Free Videos!
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
snorkeling

Experience Peanut Island Adventures

CA $68
per adult
Experience Peanut Island Adventures
See all activities in Southwest Florida

Frequently asked questions

Can I cancel my flight booking to Southwest Florida due to COVID-19?
Our convenient Customer Service Portal is your one-stop shop for most travel queries, including about flight changes and cancellations related to COVID-19. For greater peace of mind, read through the terms and conditions of your airfare before booking your next flight.
What's the best way to find cheap flights to Southwest Florida that have flexible change policies?
It's as easy as counting 1-2-3 with Expedia. Firstly, enter your preferred dates and destination and click the "Search" button. Step 2: Check "No change fee" just under the "Flexible change policies" heading to the left of your screen. Step 3. Grab your cheap and flexible ticket to Southwest Florida.
What are some of the general tips for travelers to Southwest Florida during the COVID-19 outbreak?
The COVID-19 outbreak has triggered dramatic changes to how we travel. If you plan to visit Southwest Florida, these tips will help you navigate these new challenges and rules:
  • Before booking your flight, find out if any travel bans or restrictions apply — in both your origin and destination. Keep informed with the latest updates by checking official government websites.
  • Requirements state that you must wear a face mask at the airport, including at security checkpoints. Be prepared to adjust your mask to verify your identity when asked by a TSA employee.
  • Instead of handing a TSA officer your boarding pass, position it straight on the reader yourself. When that's done, hold it up for inspection.
  • TSA now permits passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on baggage. This will have to be removed from your bag for screening.
  • Empty your personal items from your pockets, such as your wallet and phone, and place them in your carry-on instead of into bins. This will reduce handling during the screening process.
  • If you're planning to take food on the plane, place it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA officer will need to handle your food container or carry-on bag for inspection.

Which airlines fly to Southwest Florida?
Let Delta get you there. This prominent carrier provides 460 services every month to Southwest Florida Intl. Airport (RSW), a Southwest Florida gateway.
How can I find cheap tickets to Southwest Florida?
In the last seven days, was the lowest price for a flight to Southwest Florida. If you want to save even more, book well ahead of time and be flexible with your dates. Search for your journey to Southwest Florida, then check out prices for similar time frames by clicking on our "flexible dates" link.
How much is a flight to Southwest Florida?
The cost of a round-trip flight to Southwest Florida in the last seven days varied between and . If you were traveling one way from (), you could have landed a cheap fare from only .
What are the most popular airports to fly into in Southwest Florida?
Southwest Florida Intl. Airport (RSW) is the main entryway for those eager to explore Southwest Florida. Roughly 3044 flights every month touch down here.
When is the cheapest time to fly to Southwest Florida?
Jet off on a Tuesday to boost your odds of getting the cheapest fare to Southwest Florida. Mondays are usually the next most affordable day to depart. Saturday is generally the costliest day to fly anywhere.
How much is a plane ticket to Southwest Florida?
In the last seven days, fares to Southwest Florida ranged from to .
Which airlines with flights to Southwest Florida employ COVID-19 cleanliness policies?
In an effort to lessen the contact between passengers and flight crew during the current pandemic, the majority of airlines have taken physical distancing and other strategies to the skies. Just a few of these are:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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.