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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $15,276
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Viscay Hotel
South Beach
CA $2,591
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand
Reviewed on Jul 16, 2026
Pantera Rosa
South Beach
CA $1,296
per person
Sep 19 - Sep 26
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (74 reviews)
The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.
Reviewed on Jun 26, 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
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.
South End
While visiting South End, you might make a stop by sights like South Marco Beach and Marco Island Ski & Watersports.
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.
Siesta Key Village
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.
South Village
While visiting South Village, you might make a stop by sights like Safe Harbor Siesta Key and Crescent Beach.
Ready to book your vacation to Southwest Florida?
Southwest Florida Hotel Deals
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
CA $53
CA $90 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (5,832 reviews)
"Es un excelente hotel, moderno y acogedor, personal muy atento, muy buen servicio de desayuno, habitación y baño muy limpia y cómoda para una estancia corta y confortable. Volvería a visitarlo. La relación precio beneficio es excelente, es decir, un hotel económico donde sentirás que recibes más ..."
Reviewed on Aug 9, 2026
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
CA $213
CA $309 total
Aug 16 - Aug 17
includes taxes & fees
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
CA $209
CA $276 total
Aug 23 - Aug 24
includes taxes & fees
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
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.
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.
Naples Beach
9.4/10 (6,040 reviews)
Nothing says vacation like spending a lazy day at Naples Beach, a popular beach in Naples. Stroll along the seaside or visit the shops while you're in the area.
Venice Beach
9.2/10 (2,687 reviews)
Nothing says vacation like spending a lazy day at Venice Beach, a popular beach in Venice Island.
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.
What to do in Southwest Florida
Palm Beach: Sightseeing Catamaran Cruise
CA $86
per adult
100% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
CA $83
per adult
100% of travellers recommend
West Palm Beach Private Boat Cruise and Tour with a Captain
CA $409
per traveller
Frequently asked questions
How much does a Southwest Florida vacation package cost?
Less than you might think — from just CA $683, 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.
Explore a world of travel with Expedia
- Spa Hotels in Southwest Florida
- Resorts in Southwest Florida
- Motels in Southwest Florida
- Condo Rentals in Southwest Florida
- Pet-Friendly Hotels in Southwest Florida
- Hyatt Place Fort Myers Estero
- Hyatt Regency Coconut Point Resort & Spa
- Vacation Homes in Cape Coral
- Jw Marriott Marco Island Beach Resort
- All Inclusive Resorts and in Southwest Florida
- Naples Hotels
- Bonita Springs Hotels
- Pink Shell Beach Resort and Marina
- Fort Myers Beach Hotels
- Historic Hotels in Southwest Florida
- Beach Hotel Hotels in Naples
- Fort Myers Hotels
- Hotels near Southwest Florida Intl.
- Flights from Miami (MIA) to Fort Myers (RSW)
- Flights from Seattle (SEA) to Fort Myers (RSW)
- Delta Detroit (DTW) to Fort Myers (RSW) flights
- Flights from Kitchener (YKF) to Fort Myers (RSW)
- Flights from Southwest Florida Intl.
- Flights from Niagara Falls (IAG) to Fort Myers (RSW)
- Flights from Buffalo (BUF) to Fort Myers (RSW)
- Flights from Vancouver (YVR) to Fort Myers (RSW)
- Flights to Naples
- Flights from Las Vegas (LAS) to Fort Myers (RSW)
- Air Canada Toronto (YYZ) to Fort Myers (RSW) flights
- Flights from Montreal (YUL) to Fort Myers (RSW)
- Flights from Toronto (YYZ) to Naples (APF)
- Flights from Orlando (MCO) to Fort Myers (RSW)
- American Airlines Toronto (YYZ) to Fort Myers (RSW) flights
- Flights from Windsor (YQG) to Fort Myers (RSW)
- Flights from Saskatoon (YXE) to Fort Myers (RSW)
- Flights from Toronto (YTZ) to Fort Myers (RSW)
- Flights from Detroit (DTW) to Fort Myers (RSW)
- Flights to Fort Myers
- Flights from Halifax (YHZ) to Fort Myers (RSW)
- Westjet Toronto (YYZ) to Fort Myers (RSW) flights
- Flights from Syracuse (SYR) to Fort Myers (RSW)
- Flights from Toronto (YYZ) to Fort Myers (FMY)
- Flights from Toronto (YYZ) to Fort Myers (RSW)
- Flights from Calgary (YYC) to Fort Myers (RSW)
- Flights from Edmonton (YEG) to Fort Myers (RSW)
- Flights from Ottawa (YOW) to Fort Myers (RSW)
- Flights from Winnipeg (YWG) to Fort Myers (RSW)
- Flights from London (YXU) to Fort Myers (RSW)
- Flights from Hamilton (YHM) to Fort Myers (RSW)
- Flights to Southwest Florida
- Flights from Fort Lauderdale (FLL) to Fort Myers (RSW)
- Flights from Tampa (TPA) to Fort Myers (RSW)
- Visit Southwest Florida
- Centennial Park
- Pet-Friendly Vacation Packages Southwest Florida
- Fort Myers Beach Vacations
- Naples Vacations
- Coconut Point Mall
- Waterpark Vacation Packages Southwest Florida
- San Carlos Golf Club
- Cape Coral Vacations
- Bowditch Point Park
- Estero Vacations
- Fowler Street Shopping Center
- Golfview Golf and Racquet Club
- Seminole Casino Immokalee
- Naples Marina and Excursions
- Naples Zoo at Caribbean Gardens
- Manatee Park
- Burroughs Home and Gardens
- Tiburon Golf Club
- Sanibel Vacations
- Six Mile Cypress Slough Preserve
- Barefoot Beach
- Fifth Avenue South
- Bonita Springs Vacations
- Key West Express
- Naples Beach
- Edison and Ford Winter Estates
- Bunche Beach
- Vanderbilt Beach
- Little Hickory Island Beach Park
- Delnor-Wiggins Pass State Park
- Fort Myers Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
