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.
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was CA $2,093, price is now CA $888 per person
CA $888
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (3 reviews)
Great place and location! The pool was amazing.

Reviewed on May 9, 2026

MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was CA $3,278, price is now CA $1,325 per person
CA $1,325
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
2/10 (2 reviews)
Brickell Bay 3304

Brickell Bay 3304

3 out of 5
Brickell
Price was CA $2,896, price is now CA $1,248 per person
CA $1,248
per person
Jul 10 - Jul 15
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
No reviews
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $2,711, price is now CA $1,184 per person
CA $1,184
per person
Jun 25 - Jun 30
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
6/10 (2 reviews)
I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.

Reviewed on May 20, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $9,641, price is now CA $4,232 per person
CA $4,232
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 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
South Caya Costa and North Captiva Island, panorama, Florida, USA

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 $106 per night from Jun 22 to Jun 23
CA $106
CA $149 total
Jun 22 - Jun 23
includes taxes & fees
9.2/10 Wonderful! (5,389 reviews)
"Good value for money spent. The breakfast buffet was good. Staff were very helpful."

Reviewed on May 21, 2026

Kompose Boutique Hotel
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
The price is CA $327 per night from Jun 8 to Jun 9
CA $327
CA $439 total
Jun 8 - Jun 9
includes taxes & fees
9/10 Wonderful! (1,789 reviews)
"Everything was excellent except for the extra charges for parking and resort fee. I wish did the restaurants. We're open later, people are up to midnight should be able to get food. The other thing is you guys are known as markup island only because everything is so expensive in the hotel Like ..."

Reviewed on May 19, 2026

Hilton Marco Island Beach Resort and Spa
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 $225 per night from May 28 to May 29
CA $225
CA $322 total
May 28 - May 29
includes taxes & fees
9.2/10 Wonderful! (2,655 reviews)
"The property is outstanding, with service that is truly exceptional. During our time at the rooftop pool, the service was very attentive. The pool offers a spectacular view. I have visited more than five times, and I consistently find it beautiful, always wishing to return."

Reviewed on May 22, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
See all 46,781 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
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Family Vacations
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Discover the most popular places to visit in Southwest Florida

Siesta Key Beach

Siesta Key Beach

4.5/5(77 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(47 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)

Nothing says vacation like spending a lazy day at Venice Beach, a popular beach in Venice.

Venice Beach

What to do in Southwest Florida

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

CA $74
per adult
100% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Green sea turtle swimming by the snorkel trail

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

CA $82
per adult
100% of travellers recommend
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 $91
per adult
94% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
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.