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
Price was $686, price is now $500 per person
$500
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
Stay at this 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 Estero Boulevard Beach are located nearby.
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,113, price is now $743 per person
$743
per person
Jul 20 - Jul 24
found 16 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Captiva Beach and Captiva Chapel By the Sea are located nearby.
Shell Island Beach Club
East End
Save 100% on your flight
Price was $2,436, price is now $1,723 per person
$1,723
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Sanibel Island Southern Beach and Key West Express are located nearby.
Manasota Key Resort
Save 100% on your flight
Price was $1,214, price is now $869 per person
$869
per person
Jul 6 - Jul 11
found 17 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
Book a stay at this beach hotel in Englewood. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Englewood Beach and Stump Pass Beach State Park are located nearby.
Seagrape
South End
Save 100% on your flight
Price was $3,358, price is now $2,450 per person
$2,450
per person
Jul 20 - Jul 25
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Fort Myers (RSW)
Book a stay at this business-friendly vacation home in Marco Island. Enjoy free WiFi, free parking, and private pools. Popular attractions Marco Golf and Garden and Marco Island Center for the Arts are located nearby.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Save 100% on your flight
Price was $791, price is now $590 per person
$590
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
Stay at this hotel in Punta Gorda. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Lighthouse Resort and Club
East End
Save 100% on your flight
Price was $2,075, price is now $1,549 per person
$1,549
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Fort Myers (RSW)
Book a stay at this beach resort in Sanibel. Enjoy free WiFi, a beach locale, and free bicycles on site. Popular attractions Sanibel Island Southern Beach and Key West Express are located nearby.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Price was $948, price is now $708 per person
$708
per person
Jul 6 - Jul 10
found 16 hours ago
Roundtrip flight included
Indianapolis (IND) to Fort Myers (RSW)
Stay at this aparthotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage 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
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, 3 restaurants, and a beach locale. Popular attractions Key West Express and Estero Boulevard ...
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 ...
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
20091 Summerlin Road Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
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 ...
Doubletree by Hilton Fort Myers at Bell Tower Shops
13051 Bell Tower Drive 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 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.
Sun, Aug 30 - Thu, Sep 3
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$108 Roundtrip, found 8 hours ago
$108
Roundtrip
found 8 hours ago
Tue, Aug 18 - Tue, Sep 1
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Sat, Oct 3 - Fri, Oct 16
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$207 Roundtrip, found 14 hours ago
$207
Roundtrip
found 14 hours ago
Sat, Aug 29 - Thu, Sep 10
YYZ
Pearson Intl.
RSW
Southwest Florida Intl.
$233 Roundtrip, found 11 hours ago
$233
Roundtrip
found 11 hours ago
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