Search Deals onSouth Island Vacation Packages
South Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
Price was $769, price is now $535 per person
$535
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Book a stay at this 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
Price was $1,776, price is now $1,115 per person
$1,115
per person
Jul 16 - Jul 21
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
Book a stay at this 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.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Price was $770, price is now $535 per person
$535
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
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 in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Price was $792, price is now $553 per person
$553
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this aparthotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Price was $804, price is now $589 per person
$589
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this hotel in Punta Gorda. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,052, price is now $789 per person
$789
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Captiva Beach and Captiva Chapel By the Sea are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,487, price is now $1,119 per person
$1,119
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Bonita Springs Public Beach and Hertz Arena are located nearby.
THE Palmview AND Sandpiper Inns
Mid Island
Price was $1,142, price is now $865 per person
$865
per person
Jul 26 - Jul 31
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Stay at this motel in Sanibel. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club 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 Beach Resort
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 Estero Boulevard ...
GullWing Beach Resort
6620 Estero Blvd Fort Myers Beach FL
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero ...
Mariners Boathouse by Coolvacay
7630 Estero Blvd Fort Myers Beach FL
Book a stay at this beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard ...
Save an average of 15% on thousands of hotels when you're signed in
Tropical Sands Resort
7785 Estero Blvd Fort Myers Beach FL
Stay at this condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Key West Express and Estero Boulevard Beach ...
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 Estero Boulevard Beach are ...
Gullwing by Distinctive Beach Rentals
6620 Estero Blvd Fort Myers Beach FL
Book a stay at this beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard ...
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.
Tue, Aug 25 - Tue, Sep 1
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$88 Roundtrip, found 9 hours ago
$88
Roundtrip
found 9 hours ago
Tue, Sep 1 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Wed, Aug 26 - Tue, Sep 15
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Sun, Aug 23 - Sun, Sep 6
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
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