Southwest Florida Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Southwest Florida Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Price was $1,255, price is now $522 per person
$522
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Florida Keys Dive Center and Mangrove Marina are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $16,330, price is now $8,816 per person
$8,816
per person
May 13 - May 17
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,332, price is now $740 per person
$740
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
President Hotel
South Beach
Save 100% on your flight
Price was $1,280, price is now $740 per person
$740
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Penguin Hotel
South Beach
Save 100% on your flight
Price was $1,186, price is now $693 per person
$693
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Hyatt Place Miami Airport-East
Palmer Lake
Save 100% on your flight
Price was $936, price is now $566 per person
$566
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this business-friendly hotel in Miami. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kaseya Center and Brickell City Centre are located nearby.
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View all tripsTop Hotel Deals
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
107.92 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
40.23 km from city center
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff ...
Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
107.45 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
20.02 km from city center
Book a stay at this business-friendly hotel in Cape Coral. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
30.13 km from city center
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
126.37 km from city center
Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Sanibel Island Beach Resort
1231 Middle Gulf Dr Sanibel FL
37.16 km from city center
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd Marco Island FL
84.9 km from city center
Book a stay at this beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in ...
Naples Grande Beach Resort
475 Seagate Drive Naples FL
52.36 km from city center
Book a stay at this luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...
The Perry Hotel Naples
12155 Tamiami Trail N Naples FL
44.67 km from city center
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are ...
Compass by Margaritaville Hotel Naples
4805 Tamiami Trl N Naples FL
53.1 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl Sarasota FL
96.39 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff ...
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
30.1 km from city center
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Sanibel Island ...
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See all available properties in Southwest Florida
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Apr 13 - Thu, Apr 16
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Tue, May 12 - Tue, May 19
LGA
LaGuardia
TPA
Tampa Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Mon, Apr 13 - Wed, Apr 15
JFK
John F. Kennedy Intl.
TPA
Tampa Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Tue, Mar 31 - Tue, Apr 14
BOS
Logan Intl.
TPA
Tampa Intl.
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago