Search Deals onTradewinds Vacation Packages
Tradewinds Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral
Price was $583, price is now $408 per person
$408
per person
Jul 6 - Jul 13
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Edison Mall and Vietnam War Memorial are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,161, price is now $1,208 per person
$1,208
per person
Jul 6 - Jul 13
found 16 hours ago
Roundtrip non-stop 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.
Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,376, price is now $935 per person
$935
per person
Jul 27 - Aug 1
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 Gulfside City Park are located nearby.
The Perry Hotel Naples
Price was $757, price is now $517 per person
$517
per person
Jul 21 - Jul 25
found 14 hours 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.
Landing Fort Myers - Eastwood Village
Eastwood Village
Save 100% on your flight
Price was $1,029, price is now $731 per person
$731
per person
Jul 6 - Jul 13
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury aparthotel in Fort Myers. Enjoy free WiFi, free parking, and 2 outdoor pickleball courts. Popular attractions Calusa Nature Center and Planetarium and Fleamasters Fleamarket are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,297, price is now $937 per person
$937
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Bonita Springs Public Beach and Hertz Arena are located nearby.
South Seas
Save 100% on your flight
Price was $1,875, price is now $1,391 per person
$1,391
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy 3 outdoor pools, 5 restaurants, and a private beach. Popular attractions Captiva Beach and Jungle Drums are located nearby.
Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach
South End
Save 100% on your flight
Price was $4,593, price is now $3,408 per person
$3,408
per person
Jul 10 - Jul 14
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this cottage in Marco Island. Enjoy free parking, private pools, and a beach locale. Popular attractions Mackle Park and Marco Island Historical Museum 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. ...
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 3 restaurants. Our guests praise the breakfast and the pool ...
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
20091 Summerlin Road Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
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.
Thu, Aug 27 - Thu, Sep 3
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$115 Roundtrip, found 16 hours ago
$115
Roundtrip
found 16 hours ago
Wed, Aug 26 - Tue, Sep 15
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$177 Roundtrip, found 16 hours ago
$177
Roundtrip
found 16 hours ago
Sun, Aug 23 - Sun, Sep 6
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$179 Roundtrip, found 16 hours ago
$179
Roundtrip
found 16 hours ago
Tue, Aug 18 - Tue, Aug 25
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$199 Roundtrip, found 16 hours ago
$199
Roundtrip
found 16 hours ago