Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Mariners Boathouse by Coolvacay
South Island
Save 100% on your flight
Price was $696, price is now $450 per person
$450
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Lehigh Resort Club
Joel
Price was $795, price is now $583 per person
$583
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this golf aparthotel in Lehigh Acres. Enjoy free WiFi, free parking, and a golf course. Popular attractions Veterans Park and Cypress Pines Country Club are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,895, price is now $1,266 per person
$1,266
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Delnor-Wiggins Pass State Park and Vanderbilt Beach are located nearby.
Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,018, price is now $687 per person
$687
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Bowman's Beach are located nearby.
The Suites at Fishermen’s Village
Punta Gorda Isles
Save 100% on your flight
Price was $989, price is now $698 per person
$698
per person
Nov 15 - Nov 20
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
Inn at the Beach
Venice Island
Save 100% on your flight
Price was $886, price is now $627 per person
$627
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this hotel in Venice. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. Popular attractions Venice Beach and Nokomis Beach are located nearby.
Resort Harbour Properties
Punta Rassa
Save 100% on your flight
Price was $1,035, price is now $741 per person
$741
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip 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 Sanibel Island Southern Beach are located nearby.
Windward Passage Resort
Save 100% on your flight
Price was $1,276, price is now $915 per person
$915
per person
Nov 18 - Nov 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel 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.
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 ...
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 Crescent Beach ...
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. ...
Save an average of 15% on thousands of hotels when you're signed 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 ...
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 ...
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 a full-service spa. Our guests praise the breakfast and the ...
The Lighthouse Resort Inn & Suites
1051 5th St Fort Myers Beach FL
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
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 ...
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.
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Mon, Feb 8 - Sat, Feb 13
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$177 Roundtrip, just found
$177
Roundtrip
just found
Sun, Nov 15 - Sat, Dec 5
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$183 Roundtrip, just found
$183
Roundtrip
just found
Sun, Dec 6 - Mon, Dec 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
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