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Tradewinds Vacation Packages

Tradewinds Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $439, price is now $295 per person
$295
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this apartment in Fort Myers. Enjoy in-room washers/dryers, an in-room coffeemaker, and air conditioning. Popular attractions JetBlue Park at Fenway South and Calusa Nature Center and Planetarium are located nearby.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $822, price is now $521 per person
$521
per person
Oct 22 - Oct 26
found 1 day 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 Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Save 100% on your flight
Price was $518, price is now $333 per person
$333
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
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. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Save 100% on your flight
Price was $913, price is now $603 per person
$603
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
The Suites at Fishermen’s Village

The Suites at Fishermen’s Village

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $650, price is now $435 per person
$435
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Daniels Corridor
Save 100% on your flight
Price was $761, price is now $511 per person
$511
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this aparthotel in Fort Myers. Enjoy free WiFi, free parking, and a fitness center. Popular attractions JetBlue Park at Fenway South and Six Mile Cypress Slough Preserve are located nearby.
Landing Fort Myers - Eastwood Village

Landing Fort Myers - Eastwood Village

4.5 out of 5
Eastwood Village
Save 100% on your flight
Price was $881, price is now $596 per person
$596
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip 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.
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $830, price is now $564 per person
$564
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park are located nearby.

3-4 Night Vacations in Tradewinds

Price found within the past 48 hours. Click for updated prices.
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Save 100% on your flight
Price was $518, price is now $333 per person
$333
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,633, price is now $1,033 per person
$1,033
per person
Nov 5 - Nov 8
found 15 hours ago
Roundtrip flight included
Nashville (BNA) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $822, price is now $521 per person
$521
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
The Suites at Fishermen’s Village

The Suites at Fishermen’s Village

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $650, price is now $435 per person
$435
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)

5-7 Night Vacations in Tradewinds

Price found within the past 48 hours. Click for updated prices.
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Daniels Corridor
Save 100% on your flight
Price was $761, price is now $511 per person
$511
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,183, price is now $778 per person
$778
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Fort Myers (RSW)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Save 100% on your flight
Price was $913, price is now $603 per person
$603
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Fort Myers (RSW)
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $781, price is now $528 per person
$528
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Cheap Hotel Deals in Tradewinds

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
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 ...
Opens in a new windowMargaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
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 ...
Opens in a new windowLani Kai Beachfront Resort
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
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. ...
Opens in a new windowSanibel Island Beach Resort
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Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
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 ...
Opens in a new windowMarriott Sanibel Harbour Resort & Spa
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
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 ...
Opens in a new windowHoliday Inn Express Cape Coral-Fort Myers Area by IHG
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

4 out of 5
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 ...
Opens in a new windowPink Shell Beach Resort and Marina
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
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. ...
Opens in a new windowThe Lighthouse Resort Inn & Suites
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
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 ...
Opens in a new windowHilton Garden Inn Ft Myers
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.

Frontier Airlines
Fri, Sep 25 - Fri, Oct 16
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$113 Roundtrip, found 18 hours ago
$113
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Fri, Sep 25 from Hopkins Intl. to Southwest Florida Intl., returning Fri, Oct 16, priced at $113 found 18 hours ago
Frontier Airlines
Mon, Dec 7 - Sun, Dec 13
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$117 Roundtrip, found 3 hours ago
$117
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Dec 13, priced at $117 found 3 hours ago
Frontier Airlines
Sun, Dec 13 - Mon, Dec 14
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$134 Roundtrip, found 3 hours ago
$134
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Dec 13 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Mon, Dec 14, priced at $134 found 3 hours ago
Breeze Airways
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
Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Feb 6, priced at $152 found 3 hours ago