Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $585, price is now $348 per person
$348
per person
Nov 19 - Nov 23
found 18 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
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 reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,456, price is now $720 per person
$720
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Edison Beach House
Save 100% on your flight
Price was $776, price is now $463 per person
$463
per person
Dec 3 - Dec 7
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Comfort Inn & Suites
Save 100% on your flight
Price was $639, price is now $413 per person
$413
per person
Dec 6 - Dec 12
found 19 hours ago
Roundtrip flight included
Boston (BOS) 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.
Casa Playa Beach Resort
Save 100% on your flight
Price was $909, price is now $608 per person
$608
per person
Dec 3 - Dec 7
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Wiggins Pass Chalet
Save 100% on your flight
Price was $932, price is now $640 per person
$640
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4-star 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was $1,453, price is now $1,008 per person
$1,008
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 4-star golf 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.
GullWing Beach Resort
South Island
Save 100% on your flight
Price was $1,258, price is now $882 per person
$882
per person
Nov 19 - Nov 23
found 18 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express 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 ...
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 ...
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
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 ...
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 ...
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 ...
DiamondHead Beach Resort
2000 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
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 21 - Wed, Jan 28
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$102 Roundtrip, found 15 hours ago
$102
Roundtrip
found 15 hours ago
Wed, Jan 14 - Wed, Jan 21
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 6 hours ago
$112
Roundtrip
found 6 hours ago
Sun, Nov 9 - Wed, Nov 12
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$120 Roundtrip, found 15 hours ago
$120
Roundtrip
found 15 hours ago
Tue, Nov 11 - Tue, Nov 18
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 16 hours ago
$127
Roundtrip
found 16 hours ago