Southwest Florida Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was CA $2,516, price is now CA $980 per person
CA $980
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 $4,037, price is now CA $1,260 per person
CA $1,260
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
6/10 (2 reviews)
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was CA $3,751, price is now CA $1,300 per person
CA $1,300
per person
Jun 28 - Jul 4
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (2 reviews)
The room was clean, there was a problem at the check out time as all the guest have the same check out and all the elevators collapse, it took us more than an hour to get down. The parking is really a problem as we had to go up almost 20 floors. Location is pretty good.

Reviewed on Apr 14, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $9,877, price is now CA $4,368 per person
CA $4,368
per person
Jul 11 - Jul 16
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (323 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

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $1,955, price is now CA $1,059 per person
CA $1,059
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,007 reviews)
Not bad for a last-minute booking. Would consider staying here again. Near many restaurants and local adventures.

Reviewed on Apr 27, 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?

 

Choose your dates

Southwest Florida Hotel Deals

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is CA $102 per night from May 3 to May 4
CA $102
CA $115 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (2,439 reviews)
Great place to stay. Clean room and nice staff

Reviewed on Apr 27, 2026

Golden Host Resort - Sarasota
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 $312 per night from May 20 to May 21
CA $312
CA $421 total
May 20 - May 21
includes taxes & fees
9/10 Wonderful! (1,762 reviews)
The trip was absolutely incredible and as we walked out after checking out, the man standing outside that works for you, stopped us with his kind words. That’s something we will never forget! Please make sure he knows how incredible that was!

Reviewed on Apr 28, 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 $223 per night from May 22 to May 23
CA $223
CA $318 total
May 22 - May 23
includes taxes & fees
9.2/10 Wonderful! (2,521 reviews)
Great service , very clean and comfortable, large variety of restaurants and an awesome pool!

Reviewed on Apr 27, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
See all 46,967 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(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 $83
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 $71
per adult
92% 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.

Explore a world of travel with Expedia

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