Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Lani Kai Beachfront Resort
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
Edison Beach House
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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
Jul 12 - Jul 16
found 19 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
The Perry Hotel Naples
Save 100% on your flight
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Casa Playa Beach Resort
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop 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.
Hilton Naples
Central Naples
Save 100% on your flight
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naples Zoo at Caribbean Gardens and Vanderbilt Beach 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
Jul 20 - Jul 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
3-4 Night Vacations in Tradewinds
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Tradewinds
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Tradewinds
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
Stay at this 4-star beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
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 ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E, Cape Coral, FL
Book a stay at this business-friendly hotel in Cape Coral. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Save an average of 15% on thousands of hotels when you're signed in
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr, Fort Myers, FL
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property ...
Sanibel Island Beach Resort
1231 Middle Gulf Dr, Sanibel, FL
Stay at this 3-star beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
Pink Shell Beach Resort and Marina
275 Estero Blvd, Fort Myers Beach, FL
Stay at this 4-star beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
Hilton Garden Inn Ft Myers
12600 University Dr, Fort Myers, FL
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
The Lighthouse Resort Inn & Suites
1051 5th St, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular ...
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.
Thu, Jun 26 - Sat, Jun 28
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Sat, Sep 20 - Tue, Sep 23
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$120 Roundtrip, found 16 hours ago
$120
Roundtrip
found 16 hours ago
Tue, Nov 4 - Sat, Nov 8
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Sat, Aug 9 - Sat, Aug 9
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$136 Roundtrip, found 5 days ago
$136
Roundtrip
found 5 days ago