Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Inn at the Beach
Venice Island
Save 100% on your flight
Price was $626, price is now $454 per person
$454
per person
Oct 9 - Oct 13
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.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Save 100% on your flight
Price was $1,166, price is now $778 per person
$778
per person
Oct 10 - Oct 17
found 10 hours ago
Roundtrip flight included
Boston (BOS) 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.
Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,208, price is now $824 per person
$824
per person
Oct 19 - Oct 24
found 10 hours ago
Roundtrip non-stop 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 Perry Hotel Naples
Price was $1,114, price is now $793 per person
$793
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip 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.
The Suites at Fishermen’s Village
Punta Gorda Isles
Price was $1,089, price is now $783 per person
$783
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop 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.
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,002, price is now $730 per person
$730
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Landing Furnished Apartments - Naples, FL
Save 100% on your flight
Price was $1,365, price is now $1,008 per person
$1,008
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly apartment in Naples. Enjoy free WiFi, a rooftop terrace, and a fitness center. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
THE Palmview AND Sandpiper Inns
Mid Island
Price was $870, price is now $661 per person
$661
per person
Oct 19 - Oct 24
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
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
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 ...
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 ...
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. ...
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 ...
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 ...
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. ...
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.
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Fri, Sep 25 - Fri, Oct 9
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$151 Roundtrip, found 2 hours ago
$151
Roundtrip
found 2 hours ago
Thu, Nov 26 - Sun, Dec 13
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$166 Roundtrip, found 2 hours ago
$166
Roundtrip
found 2 hours ago
Sun, Dec 6 - Sun, Dec 13
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$180 Roundtrip, found 14 hours ago
$180
Roundtrip
found 14 hours ago
Discover Other Travel Deals
- Key West Express Vacations
- Bowman's Beach Vacations
- Bonita Springs Public Beach Vacations
- Estero Boulevard Beach Vacations
- Sanibel Island Lighthouse Vacations
- Bell Tower Shops Vacations
- Captiva Beach Vacations
- Bunche Beach Vacations
- Sanibel Harbour Beach Vacations
- Florida Southwestern State College Vacations
- Sanibel and Captiva Island Visitor's Center Vacations