Search Deals onSouth Island Vacation Packages
South Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Best Western Naples Inn & Suites
Moorings
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Naples Zoo at Caribbean Gardens and Fifth Avenue South are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
per person
Aug 14 - Aug 20
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 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.
Bellasera Resort
Old Naples
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Inn on Fifth
Old Naples
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
The Perry Hotel Naples
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
GreenLinks Golf Villas at Lely Resort
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star spa aparthotel in Naples. Enjoy free parking, a full-service spa, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Flamingo Island Course - Lely Resort and Swamp Buggy Races are located nearby.
The Vistas At Eastwood Apartments By Barsala
Eastwood Village
Save 100% on your flight
per person
Aug 25 - Aug 31
found 19 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Stay at this 4-star aparthotel in Fort Myers. Enjoy free WiFi, a fitness center, and in-room washers/dryers. Popular attractions Edison Mall and Calusa Nature Center and Planetarium are located nearby.
Home2 Suites Naples I-75 Pine Ridge Road, FL
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Naples Zoo at Caribbean Gardens and Vanderbilt Beach 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.
Mon, Sep 15 - Fri, Sep 26
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$68 Roundtrip, found 14 hours ago
$68
Roundtrip
found 14 hours ago
Thu, Jul 31 - Thu, Aug 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, found 6 hours ago
$90
Roundtrip
found 6 hours ago
Mon, Sep 22 - Sun, Sep 28
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Wed, Oct 29 - Tue, Nov 4
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
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