Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
per person
Aug 21 - Aug 25
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Edison Mall and Calusa Nature Center and Planetarium are located nearby.
Lani Kai Beachfront Resort
Save 100% on your flight
per person
Aug 21 - Aug 25
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Crescent Beach Family Park are located nearby.
Inn on Fifth
Old Naples
Save 100% on your flight
per person
Aug 28 - Sep 1
found 6 hours 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.
Bellasera Resort
Old Naples
Save 100% on your flight
per person
Aug 28 - Sep 1
found 6 hours 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.
Naples Grande Beach Resort
Park Shore
Save 100% on your flight
per person
Aug 16 - Aug 24
found 16 hours 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 Fifth Avenue South are located nearby.
The Vistas At Eastwood Apartments By Barsala
Eastwood Village
Save 100% on your flight
per person
Aug 17 - Aug 24
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
GreenLinks Golf Villas at Lely Resort
Save 100% on your flight
per person
Aug 28 - Sep 1
found 6 hours 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
per person
Aug 21 - Aug 25
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this 4-star eco-certified aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach 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
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 Crescent ...
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. ...
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
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 ...
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 ...
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 ...
Doubletree by Hilton Fort Myers at Bell Tower Shops
13051 Bell Tower Drive, Fort Myers, FL
Stay at this 4-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
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 ...
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, Aug 25 - Fri, Aug 29
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$59 Roundtrip, found 3 days ago
$59
Roundtrip
found 3 days ago
Tue, Aug 26 - Sat, Aug 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$100 Roundtrip, found 11 hours ago
$100
Roundtrip
found 11 hours ago
Mon, Sep 22 - Sun, Sep 28
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$110 Roundtrip, found 16 hours ago
$110
Roundtrip
found 16 hours ago
Tue, Nov 4 - Sat, Nov 8
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago