Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
Price was $762, price is now $528 per person
$528
per person
Jun 15 - Jun 19
found 13 hours ago
Roundtrip non-stop 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 $1,895, price is now $1,101 per person
$1,101
per person
Jun 15 - Jun 19
found 13 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Save 100% on your flight
Price was $1,659, price is now $1,083 per person
$1,083
per person
Jun 11 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Punta Gorda. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Save 100% on your flight
Price was $1,331, price is now $887 per person
$887
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Resort Harbour Properties
Punta Rassa
Save 100% on your flight
Price was $1,702, price is now $1,186 per person
$1,186
per person
Jun 11 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Shell Island Beach Club
East End
Save 100% on your flight
Price was $1,920, price is now $1,360 per person
$1,360
per person
Jun 13 - Jun 20
found 19 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Sanibel Island Southern Beach and Key West Express are located nearby.
THE Palmview AND Sandpiper Inns
Mid Island
Save 100% on your flight
Price was $1,433, price is now $1,036 per person
$1,036
per person
Jun 13 - Jun 20
found 19 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this motel in Sanibel. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.
Lighthouse Resort and Club
East End
Save 100% on your flight
Price was $2,455, price is now $1,797 per person
$1,797
per person
Jun 13 - Jun 20
found 19 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this resort in Sanibel. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Sanibel Island Southern Beach and Key West Express 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 - Tue, Sep 1
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Tue, Aug 25 - Sun, Sep 6
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Wed, May 27 - Tue, Jun 9
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$181 Roundtrip, found 15 hours ago
$181
Roundtrip
found 15 hours ago
Sun, Nov 1 - Sat, Nov 7
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$207 Roundtrip, found 9 hours ago
$207
Roundtrip
found 9 hours ago
Discover Other Travel Deals
- Key West Express Vacations
- Estero Boulevard Beach Vacations
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- Sanibel Island Lighthouse Vacations
- Captiva Beach Vacations
- Bunche Beach Vacations
- Bowman's Beach Vacations
- Sanibel Harbour Beach Vacations
- Lynn Hall Memorial Park Vacations
- Sanibel and Captiva Island Visitor's Center Vacations