Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,130, price is now $711 per person
$711
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,385, price is now $838 per person
$838
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Nashville (BNA) 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.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Save 100% on your flight
Price was $1,165, price is now $769 per person
$769
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach
South End
Save 100% on your flight
Price was $7,445, price is now $5,093 per person
$5,093
per person
Jul 13 - Jul 19
found 9 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this cottage in Marco Island. Enjoy free parking, private pools, and a beach locale. Popular attractions Mackle Park and Marco Island Historical Museum are located nearby.
Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,683, price is now $1,190 per person
$1,190
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Sanibel Island Southern Beach and Gulfside City Park are located nearby.
Villa Marco Island
Save 100% on your flight
Price was $1,820, price is now $1,312 per person
$1,312
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this beach villa in Marco Island. Enjoy free WiFi, free parking, and private pools. Popular attractions City of Marco Island Racquet Center and Marco Island Historical Museum are located nearby.
Matanzas Inn Bayside Resort and Marina
Price was $1,099, price is now $793 per person
$793
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
GreenLinks Golf Villas at Lely Resort
Save 100% on your flight
Price was $1,508, price is now $1,098 per person
$1,098
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this golf aparthotel in Naples. Enjoy free parking, a golf course, and 2 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Flamingo Island Course - Lely Resort and Eagle Lakes Community 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
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.
Thu, Aug 27 - Thu, Sep 3
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$92 Roundtrip, found 5 days ago
$92
Roundtrip
found 5 days ago
Tue, Aug 18 - Tue, Sep 1
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$177 Roundtrip, found 5 hours ago
$177
Roundtrip
found 5 hours ago
Sun, Aug 30 - Sat, Sep 12
YYZ
Pearson Intl.
RSW
Southwest Florida Intl.
$207 Roundtrip, found 7 hours ago
$207
Roundtrip
found 7 hours ago
Wed, May 27 - Tue, Jun 9
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
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