Southwest Florida Vacations from $482
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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.
The Latest Southwest Florida Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach
North Beach
Save 100% on your flight
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
5.8/10 (292 reviews)
The pool was nice, the condo was very basic but was fine. Until the pest control came to spray for roaches. We did not see any roaches during our stay but that did worry us for the rest of our stay. The building is aged but is in a good location.
Reviewed on Mar 17, 2025
Casa Boutique Hotel
South Beach
Save 100% on your flight
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,025 reviews)
Staff was very nice. Loungers on the beach were also nice, but it's impossible to escape the smell of marijuana on the beach - totally not the hotel's fault. Hotel lobby does have a sewage smell but thankfully our room did not smell. AC was great. Would stay again.
Reviewed on Apr 13, 2025
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 End
While visiting South End, you might make a stop by sights like South Marco Beach and Marco Island Ski & Watersports.
Find the Best Southwest Florida Vacation Packages
Southwest Florida Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tampa Intl. Airport (TPA) |
Southwest Florida Hotel Deals
Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
The price is $362 per night from May 7 to May 8
$362
includes taxes & fees
$326 per night
May 7 - May 8
8.8/10 Excellent! (1,430 reviews)
"Very clean. The staff was pleasant and helpful"
Reviewed on Apr 15, 2025
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
The price is $317 per night from May 12 to May 13
$317
includes taxes & fees
$284 per night
May 12 - May 13
8.8/10 Excellent! (1,002 reviews)
"I love my stay"
Reviewed on Apr 13, 2025
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
The price is $243 per night from Apr 23 to Apr 24
$243
includes taxes & fees
$218 per night
Apr 23 - Apr 24
8.4/10 Very Good! (1,014 reviews)
"Proximity to beach, room was perfect for two which was a King studio. Will be great when island view roof top opens. All extra charges a bit much for beach chairs etc but discount nice. Lady at Graces treated me poorly, every morning i would go for 2 large coffees and felt it was an issue to get ..."
Reviewed on Apr 13, 2025
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.
Discover the most popular places to visit in Southwest Florida
Siesta Key Beach
4.5/5(1,425 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
4.5/5(1,225 reviews)
Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.
Venice Beach
4.5/5(862 reviews)
Beachside bliss awaits at a Florida coastal gem where you can swim, fish and hunt for ancient fossils in the sand and beneath the waves.
What to do in Southwest Florida
Private Snorkeling Adventure with the Ultimate Local Expert
$110
per adult
96% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
$51
per adult
94% of travellers recommend
Guided Snorkel Experience, Free Videos in West Palm Beach
$45
per adult
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Lodging
- Hotels near Old Corkscrew Golf Club
- Hotels near Stoneybrook
- Gay friendly Hotels in Stoneybrook
- Hotels near Stoneybrook Golf Club
- Hotels near Miromar Outlets
- Hotels near Hertz Arena
- Hotels near Alico Arena
- Hotels near Corkscrew Woodlands
- Gay friendly Hotels near Corkscrew Woodlands
- Hotels near Florida Gulf Coast University
- Hotels near Corkscrew Swamp Sanctuary
- Hotels near Miromar Lakes
- Luxury Hotels near Miromar Lakes
- Waterpark Hotels in Miromar Lakes
- 4 Star Hotels in Miromar Lakes
- Casino Hotels in Miromar Lakes
- Boutique Hotels near Miromar Lakes
- Oceanfront Hotels in Miromar Lakes
- Business Hotels near Miromar Lakes
- Independent Hotels in Miromar Lakes
- Hyatt Hotels in Miromar Lakes
- Hotels near Southwest Florida Intl.
- Estero Hotels
- Cheap Hotels in Estero
- Beach Hotels in Estero
- Condo Rentals in Estero
- Pet-friendly Hotels in Estero
- Hotels with Balconies in Estero
- La Quinta Inn & Suites Hotels in Estero
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- Hotels with a Pool in Estero
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- Resorts in Estero
- Hotels with Free Breakfast in Estero
- Hotels with Restaurants in Estero
- Motels in Estero
- Vacation Homes in Estero
- Romantic Hotels in Estero
- Hotels with Hot Tubs in Estero
Flights
- Flights from Southwest Florida Intl.
- Flights from Chicago (ORD) to Fort Myers (RSW)
- Flights from Boston (BOS) to Fort Myers (RSW)
- Flights from Minneapolis (MSP) to Fort Myers (RSW)
- Flights from Philadelphia (PHL) to Fort Myers (RSW)
- Flights from Detroit (DTW) to Fort Myers (RSW)
- Flights from Cleveland (CLE) to Fort Myers (RSW)
- Flights from New York (NYC) to Fort Myers (RSW)
- Flights to Estero
- Flights from Milwaukee (MKE) to Fort Myers (RSW)
- Flights from Pittsburgh (PIT) to Fort Myers (RSW)
- Flights from Estero
Cars
- Car rental Fort Myers Airport (RSW)
- Car rentals near Miromar Outlets
- Car rentals near Alico Arena
- Car rentals near Hertz Arena
- Van Car Rentals near Hertz Arena
- Fullsize Car Rentals near Hertz Arena
- Car rentals near Florida Gulf Coast University
- Car rentals near Corkscrew Swamp Sanctuary
- Hertz Rental Cars in Miromar Lakes
- Budget Rental Cars in Miromar Lakes
- Right Cars Rental Cars in Miromar Lakes
- Advantage Rent-A-Car Rental Cars in Miromar Lakes
- Standard Car Rentals in Miromar Lakes
- Top Rent a Car Rental Cars in Miromar Lakes
- Smile Rental Cars in Miromar Lakes
- Click & Rent Rental Cars in Miromar Lakes
- Express Travel Group Rental Cars in Miromar Lakes
- Car rentals near Three Oaks
- Car rentals near Estero
- Budget Rental Cars in Estero
- Hertz Rental Cars in Estero
- National Car Rental Rental Cars in Estero
- Enterprise Rental Cars in Estero
- Thrifty Car Rental Rental Cars in Estero
Vacation Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.