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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.
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
Save 100% on your flight
Price was $563, price is now $362 per person
$362
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Save 100% on your flight
Price was $1,101, price is now $552 per person
$552
per person
Dec 17 - Dec 20
found 1 hour ago
Roundtrip flight included
Hartford (BDL) 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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Save 100% on your flight
Price was $757, price is now $389 per person
$389
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $5,080, price is now $3,085 per person
$3,085
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $1,458, price is now $887 per person
$887
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3.5-star beach resort in Captiva. Enjoy 3 outdoor pools, 6 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $708, price is now $440 per person
$440
per person
Nov 7 - Nov 10
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, 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.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $933, price is now $588 per person
$588
per person
Dec 14 - Dec 20
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.
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
Price was $823, price is now $540 per person
$540
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3.5-star business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall 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
Price was $502, price is now $314 per person
$314
per person
Nov 7 - Nov 10
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,101, price is now $552 per person
$552
per person
Dec 17 - Dec 20
found 1 hour ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $708, price is now $440 per person
$440
per person
Nov 7 - Nov 10
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,261, price is now $809 per person
$809
per person
Dec 17 - Dec 20
found 1 hour ago
Roundtrip 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 $757, price is now $389 per person
$389
per person
Dec 14 - Dec 20
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 $1,840, price is now $854 per person
$854
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop 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 $822, price is now $426 per person
$426
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,053, price is now $629 per person
$629
per person
Nov 15 - Nov 20
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.

Breeze Airways
Wed, Jan 21 - Wed, Jan 28
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Jan 21 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Jan 28, priced at $107 found 3 days ago
Spirit Airlines
Mon, Nov 3 - Fri, Nov 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$111 Roundtrip, found 2 hours ago
$111
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, Nov 3 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Nov 14, priced at $111 found 2 hours ago
United
Tue, Nov 11 - Tue, Nov 18
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 2 hours ago
$127
Roundtrip
found 2 hours 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 2 hours ago
Frontier Airlines
Sun, Nov 9 - Thu, Nov 13
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$128 Roundtrip, found 4 days ago
$128
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Nov 9 from Philadelphia Intl. to Southwest Florida Intl., returning Thu, Nov 13, priced at $128 found 4 days ago