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.
Tideline Palm Beach Ocean Resort and Spa

Tideline Palm Beach Ocean Resort and Spa

4 out of 5
Price was CA $3,254, price is now CA $1,818 per person
CA $1,818
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Lauderdale (FLL)
7.8/10 Good! (356 reviews)
No fue lo q imaginaba en cuanto al desayuno y restaurante ,pero el personal fue muy atento.

Reviewed on Jun 9, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $13,478, price is now CA $6,182 per person
CA $6,182
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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

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 $24,467, price is now CA $12,845 per person
CA $12,845
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $4,313, price is now CA $2,332 per person
CA $2,332
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1,145 reviews)
The room was always super, super clean. All of the staff members were amazing, and always extremely kind&helpful. The beach view was beautiful, the breakfast was outstanding we were always excited to have breakfast, the buffet&food was delicious.

Reviewed on Jun 12, 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $6,529, price is now CA $3,761 per person
CA $3,761
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,545 reviews)
We love everything Our favorite hotel

Reviewed on Jun 11, 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 $99 per night from Jul 6 to Jul 7
CA $99
CA $142 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (5,550 reviews)
"Love this place"

Reviewed on Jun 12, 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 $219 per night from Jul 6 to Jul 7
CA $219
CA $316 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (2,797 reviews)
"Debería existir un local de cuido para los niños de los huésped"

Reviewed on Jun 12, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jun 15 to Jun 16
CA $232
CA $302 total
Jun 15 - Jun 16
includes taxes & fees
9.4/10 Exceptional! (2,259 reviews)
"The view from our balcony was beautiful but no privacy from the other balconies. The room was average at best, very hot upon arrival and multiple outlets didn’t work. The water pressure from the bathroom sink was pathetic. The pool was very cloudy all week, either a result of improper water chemistry ..."

Reviewed on Jun 12, 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 46,759 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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Stay near popular Southwest Florida attractions

Siesta Key Beach

4.8/5 (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

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.