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 $883, price is now $671 per person
$671
per person
Dec 3 - Dec 7
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Sanibel Island Southern Beach are located nearby.
Landing Incredible 1bd, Gym, Clubhouse
Hancock
Price was $1,764, price is now $1,283 per person
$1,283
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Villa Marco Island
Price was $1,998, price is now $1,478 per person
$1,478
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach villa in Marco Island. Enjoy free WiFi, free parking, and private pools. Popular attractions Marco Beach and South Marco Beach are located nearby.
The Perry Hotel Naples
Price was $990, price is now $758 per person
$758
per person
Dec 3 - Dec 7
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 Barefoot Beach are located nearby.
The Suites at Fishermen’s Village
Punta Gorda Isles
Price was $945, price is now $727 per person
$727
per person
Dec 3 - Dec 7
found 24 hours 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.
Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby
Naples Park
Price was $964, price is now $744 per person
$744
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Fort Myers (RSW)
Stay at this apartment in Naples. Enjoy free parking and patios. Popular attractions Vanderbilt Beach and Tiburon Golf Club are located nearby.
Surfside Cottage by Avantstay Patio + BBQ Dog-friendly Lake Access Mins to Gulf Beaches
Naples Park
Price was $964, price is now $744 per person
$744
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Fort Myers (RSW)
Stay at this apartment in Naples. Enjoy free parking, patios, and air conditioning. Popular attractions Vanderbilt Beach and Tiburon Golf Club are located nearby.
The June
Mid Island
Price was $1,953, price is now $1,507 per person
$1,507
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Stay at this condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Mound House 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 ...
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. ...
Save an average of 15% on thousands of hotels when you're signed in
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 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. ...
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.
Mon, Jan 11 - Fri, Jan 22
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Sun, Dec 13 - Thu, Jan 7
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$104 Roundtrip, just found
$104
Roundtrip
just found
Mon, Jan 11 - Fri, Jan 22
TTN
Mercer
RSW
Southwest Florida Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Mon, Dec 7 - Mon, Dec 21
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$148 Roundtrip, found 23 hours ago
$148
Roundtrip
found 23 hours ago