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.
Wiggins Pass Chalet
Price was $797, price is now $577 per person
$577
per person
Dec 3 - Dec 8
found 22 hours ago
Roundtrip flight included
Akron (CAK) to Fort Myers (RSW)
Stay at this 4-star business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular attractions Barefoot Beach and Vanderbilt Beach are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,660, price is now $850 per person
$850
per person
Dec 3 - Dec 8
found 22 hours ago
Roundtrip flight included
Akron (CAK) 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.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,294, price is now $674 per person
$674
per person
Dec 3 - Dec 8
found 22 hours ago
Roundtrip flight included
Akron (CAK) 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.
Inn on Fifth
Old Naples
Save 100% on your flight
Price was $1,524, price is now $1,027 per person
$1,027
per person
Dec 3 - Dec 8
found 22 hours ago
Roundtrip flight included
Akron (CAK) to Fort Myers (RSW)
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
Embassy Suites by Hilton Fort Myers Estero
Save 100% on your flight
Price was $883, price is now $613 per person
$613
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall are located nearby.
Casa Playa Beach Resort
Save 100% on your flight
Price was $1,120, price is now $781 per person
$781
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park 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.
Sat, Feb 7 - Sat, Feb 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
Sat, Feb 7 - Sat, Feb 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$106 Roundtrip, found 5 days ago
$106
Roundtrip
found 5 days ago
Sat, Feb 28 - Fri, Mar 6
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Mon, Dec 8 - Wed, Dec 24
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$131 Roundtrip, found 2 days ago
$131
Roundtrip
found 2 days ago
Wed, Jan 14 - Sat, Jan 17
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$132 Roundtrip, found 15 hours ago
$132
Roundtrip
found 15 hours ago