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.
Le Particulier Miami
Mid Beach
Price was $1,086, price is now $461 per person
$461
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Bay Breeze Premium Apartments By Eskape Collection
Price was $1,463, price is now $606 per person
$606
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this family-friendly aparthotel in Bay Harbor Islands. Enjoy free WiFi, private pools, and a rooftop terrace. Popular attractions Aventura Mall and Miami Beach Boardwalk are located nearby.
Maison Felix
North Beach
Price was $1,597, price is now $741 per person
$741
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy a 24-hour front desk, daily housekeeping, and a garden. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Brickell Floor 31 Sea View-Free Parking by Palermo Home
Downtown Miami
Price was $1,571, price is now $776 per person
$776
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this apartment in Miami. Enjoy free WiFi, in-room washers/dryers, and an outdoor pool. Popular attractions Bayside Marketplace and Kaseya Center are located nearby.
Fort Lauderdale Marriott Pompano Beach Resort
Price was $1,485, price is now $768 per person
$768
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this beach hotel in Pompano Beach. Enjoy a beach locale, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pompano Beach and Hillsboro Inlet Lighthouse are located nearby.
The Penguin Hotel
South Beach
Save 100% on your flight
Price was $2,129, price is now $1,132 per person
$1,132
per person
Feb 7 - Feb 14
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
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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 ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
20.01 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 ...
Naples Grande Beach Resort
475 Seagate Drive Naples FL
52.47 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 ...
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 ...
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 ...
Inn on Fifth
699 5th Ave S Naples FL
60.19 km from city center
Book a stay at this spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
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, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent ...
Carlisle Inn
3727 Bahia Vista Sarasota FL
99.31 km from city center
Stay at this hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
126.44 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 ...
Hyatt Vacation Club at Coconut Cove, Bonita Springs
11800 Coconut Cove Drive Bonita Springs FL
30.9 km from city center
Book a stay at this golf aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita ...
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 ...
DiamondHead Beach Resort
2000 Estero Blvd Fort Myers Beach FL
29.95 km from city center
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
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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.
Wed, Jan 21 - Fri, Jan 30
TTN
Mercer
TPA
Tampa Intl.
$58 Roundtrip, found 5 days ago
$58
Roundtrip
found 5 days ago
Fri, Feb 6 - Tue, Feb 10
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$60 Roundtrip, just found
$60
Roundtrip
just found
Tue, Feb 10 - Wed, Feb 25
LGA
LaGuardia
TPA
Tampa Intl.
$117 Roundtrip, found 21 hours ago
$117
Roundtrip
found 21 hours ago
Mon, Jan 19 - Thu, Feb 5
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago