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
Price was $1,146, price is now $757 per person
$757
per person
Dec 26 - Jan 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this 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 Edison Mall and Barbara B Mann Hall are located nearby.
Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $1,584, price is now $839 per person
$839
per person
Dec 25 - Dec 31
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.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $6,111, price is now $3,424 per person
$3,424
per person
Dec 26 - Jan 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,316, price is now $769 per person
$769
per person
Jan 4 - Jan 10
found 1 hour ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this 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.
The Perry Hotel Naples
Save 100% on your flight
Price was $2,767, price is now $1,635 per person
$1,635
per person
Dec 26 - Jan 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Home2 Suites by Hilton Fort Myers Colonial Blvd
Price was $1,257, price is now $835 per person
$835
per person
Dec 26 - Jan 3
found 21 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 helpful staff in our reviews. Popular attractions Edison Mall and Six Mile Cypress Slough Preserve are located nearby.
Marriott Sanibel Harbour Resort & Spa
Punta Rassa
Save 100% on your flight
Price was $2,441, price is now $1,631 per person
$1,631
per person
Dec 26 - Jan 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
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 condition in our reviews. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby.
Embassy Suites by Hilton Fort Myers Estero
Save 100% on your flight
Price was $1,517, price is now $1,043 per person
$1,043
per person
Dec 26 - Jan 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall 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
Book a stay at this 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 ...
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent ...
Save an average of 15% on thousands of hotels when you're signed in
Sanibel Island Beach Resort
1231 Middle Gulf Dr Sanibel FL
Book a stay at this 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
Book a stay at this 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
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
DiamondHead Beach Resort
2000 Estero Blvd Fort Myers Beach FL
Book a stay at this 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 ...
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 ...
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, Jan 13 - Wed, Jan 21
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$60 Roundtrip, found 9 hours ago
$60
Roundtrip
found 9 hours ago
Mon, Nov 24 - Sat, Dec 6
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$74 Roundtrip, found 5 hours ago
$74
Roundtrip
found 5 hours ago
Sun, Dec 14 - Thu, Dec 25
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$110 Roundtrip, found 20 hours ago
$110
Roundtrip
found 20 hours ago
Mon, Dec 8 - Wed, Dec 10
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$122 Roundtrip, found 20 hours ago
$122
Roundtrip
found 20 hours ago