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Tradewinds Vacation Packages

Tradewinds Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,275, price is now $887 per person
$887
per person
Mar 22 - Mar 26
found 10 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
Stay at this condo in Punta Gorda. Enjoy free WiFi, free parking, and a marina. 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.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $3,826, price is now $2,612 per person
$2,612
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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.
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Pelican Bay
Save 100% on your flight
Price was $2,826, price is now $1,973 per person
$1,973
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
Book a stay at this luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Naples Zoo at Caribbean Gardens are located nearby.
Home2 Suites by Hilton Fort Myers Colonial Blvd

Home2 Suites by Hilton Fort Myers Colonial Blvd

3 out of 5
Save 100% on your flight
Price was $1,369, price is now $964 per person
$964
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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 helpful staff in our reviews. Popular attractions Edison Mall and Six Mile Cypress Slough Preserve are located nearby.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,273, price is now $906 per person
$906
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $3,116, price is now $2,231 per person
$2,231
per person
Mar 9 - Mar 14
found 8 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
Book a stay at this golf aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
Redevelopment Area
Save 100% on your flight
Price was $2,041, price is now $1,482 per person
$1,482
per person
Mar 10 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Save 100% on your flight
Price was $1,378, price is now $1,006 per person
$1,006
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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.

3-4 Night Vacations in Tradewinds

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $1,014, price is now $690 per person
$690
per person
Feb 27 - Mar 2
found 21 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $3,826, price is now $2,612 per person
$2,612
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,275, price is now $887 per person
$887
per person
Mar 22 - Mar 26
found 10 hours ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Pelican Bay
Save 100% on your flight
Price was $2,826, price is now $1,973 per person
$1,973
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)

5-7 Night Vacations in Tradewinds

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $1,386, price is now $885 per person
$885
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Fort Myers (RSW)
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,782, price is now $1,058 per person
$1,058
per person
Mar 2 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,741, price is now $1,729 per person
$1,729
per person
Mar 7 - Mar 14
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 $1,911, price is now $1,277 per person
$1,277
per person
Mar 8 - Mar 15
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) to Fort Myers (RSW)

Cheap Hotel Deals in Tradewinds

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
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, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent ...
Opens in a new windowLani Kai Beachfront Resort
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
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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
DiamondHead Beach Resort

DiamondHead Beach Resort

3.5 out of 5
2000 Estero Blvd Fort Myers Beach FL
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
Opens in a new windowDiamondHead Beach Resort
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 3 restaurants. Our guests praise the breakfast and the pool ...
Opens in a new windowPink Shell Beach Resort and Marina
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
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
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
Sat, Feb 21 - Thu, Feb 26
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$58 Roundtrip, found 22 hours ago
$58
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Feb 26, priced at $58 found 22 hours ago
Frontier Airlines
Sun, Feb 15 - Thu, Feb 26
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$74 Roundtrip, found 2 days ago
$74
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Feb 15 from Philadelphia Intl. to Southwest Florida Intl., returning Thu, Feb 26, priced at $74 found 2 days ago
Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 5 hours ago
$98
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Logan Intl. to Southwest Florida Intl., returning Wed, Mar 4, priced at $98 found 5 hours ago
Frontier Airlines
Sat, Feb 14 - Fri, Feb 20
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 7 hours ago
$98
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Hopkins Intl. to Southwest Florida Intl., returning Fri, Feb 20, priced at $98 found 7 hours ago