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.
Cavalier Hotel South Beach
South Beach
Price was $1,193, price is now $552 per person
$552
per person
Mar 1 - Mar 6
found 19 hours ago
Roundtrip flight included
New York (JFK) 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.
Solé Miami, A Noble House Resort
Ocean Four
Price was $1,232, price is now $604 per person
$604
per person
Mar 1 - Mar 6
found 19 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Book a stay at this beach hotel in Sunny Isles Beach. Enjoy a beach locale, breakfast (surcharge), and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Aventura Mall and Gulfstream Park Racing and Casino are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $21,682, price is now $10,900 per person
$10,900
per person
Apr 15 - Apr 20
found 22 hours ago
Roundtrip flight included
Raleigh (RDU) 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.
President Hotel
South Beach
Price was $1,318, price is now $692 per person
$692
per person
Mar 1 - Mar 6
found 19 hours ago
Roundtrip flight included
New York (JFK) 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 $1,050, price is now $559 per person
$559
per person
Mar 1 - Mar 6
found 19 hours ago
Roundtrip flight included
New York (JFK) 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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View all tripsTop Hotel Deals
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 ...
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 ...
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. ...
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 ...
Marco Beach Ocean Suites
480 S Collier Blvd Marco Island FL
84.48 km from city center
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
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 ...
Lido Beach Resort
700 Benjamin Franklin Dr Sarasota FL
104.11 km from city center
Book a stay at this beach resort in Sarasota. Enjoy free WiFi, 2 outdoor pools, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
JW Marriott Marco Island Beach Resort
400 S Collier Blvd Marco Island FL
84.16 km from city center
Book a stay at this beach resort in Marco Island. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff and the property ...
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 ...
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 ...
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 ...
Bayfront Inn Fifth Avenue
1221 5th Ave S Naples FL
60.01 km from city center
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
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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.
Sun, Feb 22 - Thu, Feb 26
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Mon, Feb 16 - Wed, Feb 18
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Fri, Mar 13 - Sat, Mar 21
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Sun, Feb 8 - Thu, Feb 26
JFK
John F. Kennedy Intl.
RSW
Southwest Florida Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Sat, Feb 21 - Tue, Feb 24
LGA
LaGuardia
TPA
Tampa Intl.
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago