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 $1,262, price is now $529 per person
$529
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Bay Breeze Premium Apartments By Eskape Collection
Price was $1,694, price is now $795 per person
$795
per person
Mar 19 - Mar 25
found 22 hours ago
Roundtrip flight included
Boston (BOS) 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.
Kompose Boutique Hotel
Price was $1,154, price is now $557 per person
$557
per person
Feb 1 - Feb 8
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
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 and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $24,196, price is now $11,890 per person
$11,890
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Hawks Cay Resort
Price was $1,250, price is now $617 per person
$617
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Little Conch Key and Walkers Island are located nearby.
Pelican Hotel
South Beach
Price was $2,171, price is now $1,085 per person
$1,085
per person
Mar 19 - Mar 25
found 22 hours ago
Roundtrip flight included
Boston (BOS) 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 helpful staff and the clean rooms in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
Don't see what you're looking for?
See all available trips from Columbus to Southwest Florida
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
Fairways Inn of Naples
103 Palm River Blvd Naples FL
45.59 km from city center
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
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. ...
Don't see what you're looking for?
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, Jan 25 - Thu, Feb 12
TTN
Mercer
TPA
Tampa Intl.
$68 Roundtrip, found 16 hours ago
$68
Roundtrip
found 16 hours ago
Tue, Feb 17 - Tue, Feb 24
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$70 Roundtrip, found 13 hours ago
$70
Roundtrip
found 13 hours ago
Sun, Feb 1 - Wed, Feb 4
EWR
Newark Liberty Intl. Airport
TPA
Tampa Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Tue, Jan 20 - Sat, Jan 24
BOS
Logan Intl.
TPA
Tampa Intl.
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago