Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $823, price is now $468 per person
$468
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, 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.
Edison Beach House
Save 100% on your flight
Price was $872, price is now $527 per person
$527
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
The Perry Hotel Naples
Save 100% on your flight
Price was $902, price is now $582 per person
$582
per person
Dec 10 - Dec 14
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
Price was $1,071, price is now $694 per person
$694
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Comfort Inn & Suites
Save 100% on your flight
Price was $774, price is now $504 per person
$504
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
Inn on Fifth
Old Naples
Save 100% on your flight
Price was $1,521, price is now $996 per person
$996
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
South Seas Resort
Save 100% on your flight
Price was $932, price is now $639 per person
$639
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3.5-star beach resort in Captiva. Enjoy 3 outdoor pools, 6 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.
Pink Shell Beach Resort and Marina
Save 100% on your flight
Price was $742, price is now $515 per person
$515
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
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 in our reviews. Popular attractions Key West Express and Bowditch Point Park 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 ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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. ...
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 ...
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 ...
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.
Wed, Jan 14 - Wed, Jan 28
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Fri, Dec 5 - Fri, Dec 19
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Sun, Dec 7 - Mon, Dec 8
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
Tue, Nov 11 - Tue, Nov 18
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 8 hours ago
$127
Roundtrip
found 8 hours ago