Search Deals onSouth Island Vacation Packages
South Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Wyvern Hotel, an Ascend Collection Hotel
Downtown Punta Gorda
Save 100% on your flight
Price was $1,527, price is now $1,049 per person
$1,049
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury hotel 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 A. C. Freeman House and Gilchrist Park are located nearby.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Save 100% on your flight
Price was $1,869, price is now $1,128 per person
$1,128
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this condo in Punta Gorda. Enjoy free WiFi, free parking, and a marina. 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.
The Perry Hotel Naples
Save 100% on your flight
Price was $2,549, price is now $1,606 per person
$1,606
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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
Save 100% on your flight
Price was $4,323, price is now $2,908 per person
$2,908
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Southseas
Save 100% on your flight
Price was $4,071, price is now $2,748 per person
$2,748
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach apartment in Marco Island. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Tigertail Beach and Sand Dollar Island Beach and Landing are located nearby.
Innovation Hotel
Save 100% on your flight
Price was $2,159, price is now $1,533 per person
$1,533
per person
Mar 5 - Mar 12
found 10 hours 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 helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
The Boat House
Olde Marco
Save 100% on your flight
Price was $1,658, price is now $1,200 per person
$1,200
per person
Mar 5 - Mar 12
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this hotel in Marco Island. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pelican Pier Marina and Cannon Beach are located nearby.
Wiggins Pass Chalet
Save 100% on your flight
Price was $1,466, price is now $1,068 per person
$1,068
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this 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.
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 Bonita Springs ...
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 Bonita ...
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 ...
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 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.
Tue, Feb 24 - Wed, Mar 4
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$59 Roundtrip, found 15 hours ago
$59
Roundtrip
found 15 hours ago
Tue, Feb 24 - Tue, Mar 3
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 15 hours ago
$98
Roundtrip
found 15 hours ago
Tue, Feb 17 - Thu, Feb 19
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 13 hours ago
$98
Roundtrip
found 13 hours ago
Mon, Feb 16 - Fri, Feb 20
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 15 hours ago
$98
Roundtrip
found 15 hours ago
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