Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Stay Inn & Suites
Winkler
Price was $563, price is now $426 per person
$426
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Fort Myers. Enjoy free WiFi, free parking, and room service. Popular attractions The Ranch Concert Hall & Saloon and Edison Mall are located nearby.
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,008, price is now $603 per person
$603
per person
Sep 23 - Sep 27
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Bowman's Beach and Captiva Beach are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $771, price is now $485 per person
$485
per person
Sep 30 - Oct 4
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 Vanderbilt Beach and Delnor-Wiggins Pass State Park are located nearby.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Save 100% on your flight
Price was $786, price is now $547 per person
$547
per person
Sep 23 - Sep 27
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this spa hotel in Punta Gorda. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Price was $665, price is now $477 per person
$477
per person
Sep 23 - Sep 27
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Beach Ocean Suites
South End
Save 100% on your flight
Price was $2,383, price is now $1,740 per person
$1,740
per person
Oct 3 - Oct 10
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions South Marco Beach and Marco Beach are located nearby.
Vanderbilt Beach Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,435, price is now $1,058 per person
$1,058
per person
Oct 3 - Oct 10
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel in Naples. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass State 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 Estero Boulevard ...
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.
Sun, Nov 15 - Sat, Dec 5
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$133 Roundtrip, found 2 hours ago
$133
Roundtrip
found 2 hours ago
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$152 Roundtrip, found 3 hours ago
$152
Roundtrip
found 3 hours ago
Sun, Dec 13 - Thu, Jan 7
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Tue, Nov 17 - Thu, Nov 19
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$207 Roundtrip, found 4 hours ago
$207
Roundtrip
found 4 hours ago
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