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Truckland Vacation Packages

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Truckland Flight + Hotel Packages

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
Save 100% on your flight
Price was $543, price is now $297 per person
$297
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Price was $1,443, price is now $686 per person
$686
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this 4.5-star 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.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
Save 100% on your flight
Price was $566, price is now $310 per person
$310
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Calusa Nature Center and Planetarium and Topgolf are located nearby.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,280, price is now $723 per person
$723
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $937, price is now $531 per person
$531
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this 4.5-star luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $676, price is now $389 per person
$389
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
Price was $1,050, price is now $606 per person
$606
per person
Nov 13 - Nov 16
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $1,189, price is now $717 per person
$717
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly condo 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 Pier are located nearby.

Truckland Vacation Packages 3-4 Night Stays

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 $543, price is now $297 per person
$297
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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
Price was $1,443, price is now $686 per person
$686
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Price was $884, price is now $455 per person
$455
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Save 100% on your flight
Price was $566, price is now $310 per person
$310
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)

Truckland Vacation Packages 5-7 Night Stays

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 $697, price is now $340 per person
$340
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
Price was $3,004, price is now $1,295 per person
$1,295
per person
Nov 15 - Nov 21
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
Price was $1,397, price is now $628 per person
$628
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,913, price is now $990 per person
$990
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Jan 13 - Wed, Jan 21
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jan 13 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Jan 21, priced at $110 found 2 days ago
Breeze Airways
Wed, Jan 21 - Wed, Jan 28
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Jan 21 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Jan 28, priced at $112 just found
United
Tue, Nov 11 - Tue, Nov 18
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select United flight, departing Tue, Nov 11 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Tue, Nov 18, priced at $127 found 1 day ago
JetBlue Airways
Mon, Nov 10 - Thu, Nov 13
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 6 hours ago
$127
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Mon, Nov 10 from Logan Intl. to Southwest Florida Intl., returning Thu, Nov 13, priced at $127 found 6 hours ago