Search Deals onSouth Island Vacation Packages
South Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Edison Beach House
Save 100% on your flight
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Lani Kai Beachfront Resort
Save 100% on your flight
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Times Square are located nearby.
Inn on Fifth
Old Naples
Save 100% on your flight
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) 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.
Casa Playa Beach Resort
Save 100% on your flight
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Naples Grande Beach Resort
Park Shore
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 4.5-star 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 our reviews. Popular attractions Vanderbilt Beach and Naples Zoo at Caribbean Gardens are located nearby.
Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach
South End
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star cottage in Marco Island. Enjoy free parking, private pools, and patios. Popular attractions Mackle Park and Marco Island Historical Museum are located nearby.
Bellasera Resort
Old Naples
Save 100% on your flight
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Book a stay at this business-friendly condo in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
3-4 Night Vacations in South Island
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in South Island
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in South Island
Pointe Estero
6640 Estero Blvd, Fort Myers Beach, FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free parking, a beach locale, and a garden. Popular attractions Key West Express and Bonita Springs ...
GullWing Beach Resort
6620 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita ...
Gullwing
6620 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita Springs ...
Save an average of 15% on thousands of hotels when you're signed in
Carribean Beach Club
7600 Estero Blvd, Fort Myers Beach, FL
Stay at this condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita Springs Public Beach ...
Lowest 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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Sep 14 - Fri, Sep 19
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Thu, Sep 4 - Sun, Sep 7
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Mon, Sep 22 - Sun, Sep 28
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Wed, Oct 29 - Tue, Nov 4
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
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