Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa
Punta Rassa
Price was $948, price is now $734 per person
$734
per person
Nov 11 - Nov 15
found 10 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
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 condition in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Landing Incredible 1bd, Gym, Clubhouse
Hancock
Price was $1,164, price is now $894 per person
$894
per person
Nov 16 - Nov 23
found 20 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this apartment in North Fort Myers. Enjoy free parking, an outdoor pool, and a fitness center. Popular attractions Pine Island Shopping Center and Fort Myers Shopping Center are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $2,619, price is now $1,605 per person
$1,605
per person
Nov 21 - Nov 29
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 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 $5,047, price is now $3,683 per person
$3,683
per person
Nov 21 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Bellasera Resort
Old Naples
Save 100% on your flight
Price was $2,969, price is now $2,227 per person
$2,227
per person
Nov 21 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Tween Waters Island Resort & Spa
Price was $1,122, price is now $852 per person
$852
per person
Nov 11 - Nov 15
found 10 hours ago
Roundtrip flight included
Hartford (BDL) 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 Captiva Beach and Captiva Chapel By the Sea are located nearby.
Shell Island Beach Club
East End
Price was $2,208, price is now $1,703 per person
$1,703
per person
Nov 21 - Nov 28
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby.
Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples
Save 100% on your flight
Price was $2,542, price is now $1,969 per person
$1,969
per person
Nov 14 - Nov 20
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Stay at this cottage in Bonita Springs. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Barefoot Beach and Bonita Springs Public Beach 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
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. ...
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 ...
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. ...
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 ...
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 ...
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.
Tue, Dec 1 - Tue, Dec 8
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$103 Roundtrip, found 12 hours ago
$103
Roundtrip
found 12 hours ago
Mon, Dec 7 - Sun, Dec 13
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$118 Roundtrip, found 16 hours ago
$118
Roundtrip
found 16 hours ago
Sun, Nov 15 - Sat, Dec 5
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$153 Roundtrip, found 15 hours ago
$153
Roundtrip
found 15 hours ago
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$193 Roundtrip, found 4 hours ago
$193
Roundtrip
found 4 hours ago