South End Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Lisa Warmouth Strusowski
South End Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $572, price is now $339 per person
$339
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $926, price is now $538 per person
$538
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 4.5-star luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,291, price is now $1,354 per person
$1,354
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4.5-star luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Edison Beach House
Save 100% on your flight
Price was $700, price is now $428 per person
$428
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.
Hyatt Place Fort Myers/at The Forum
The Forum
Price was $572, price is now $357 per person
$357
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Calusa Nature Center and Planetarium and Topgolf are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was $707, price is now $493 per person
$493
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4-star eco-certified aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
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, Dec 8 - Thu, Dec 11
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Thu, Oct 30 - Fri, Oct 31
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$122 Roundtrip, found 6 days ago
$122
Roundtrip
found 6 days ago
Tue, Oct 7 - Sat, Oct 11
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Sun, Oct 12 - Thu, Oct 16
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Thu, Oct 2 - Sun, Oct 12
YYZ
Pearson Intl.
RSW
Southwest Florida Intl.
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago