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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.
Olde Marco Island Inn and Suites

Olde Marco Island Inn and Suites

3 out of 5
Save 100% on your flight
Price was $830, price is now $540 per person
$540
per person
Dec 3 - Dec 8
found 4 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this hotel in Marco Island. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Marco Beach and Pelican Pier Marina are located nearby.

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,695, price is now $959 per person
$959
per person
Dec 11 - Dec 15
found 12 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.

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,363, price is now $915 per person
$915
per person
Dec 17 - Dec 22
found 16 hours ago
Roundtrip flight included
Hartford (BDL) 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.

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $1,029, price is now $691 per person
$691
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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 Bowman's Beach are located nearby.
50 yard walk to sand and Gulf of America

Reviewed on Sep 28, 2026

Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Save 100% on your flight
Price was $1,373, price is now $924 per person
$924
per person
Dec 21 - Dec 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.
Very Clean

Reviewed on Sep 9, 2026

Spinnaker Inn of Naples

Spinnaker Inn of Naples

2 out of 5
Price was $825, price is now $592 per person
$592
per person
Dec 9 - Dec 13
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and cable TV channels. Our guests praise the clean rooms in our reviews. Popular attractions Tiburon Golf Club and Fifth Avenue South are located nearby.

Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
Price was $860, price is now $616 per person
$616
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $995, price is now $714 per person
$714
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Best resort/vacation I’ve ever had in Florida. Four pools a lazy river two hot tubs two bars and a restaurant. And the private island! We will definitely be back. The staff was beyond nice and courteous. Do not hesitate to book a stay here.

Reviewed on Sep 28, 2026

Truckland Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Olde Marco Island Inn and Suites

Olde Marco Island Inn and Suites

3 out of 5
Olde Marco
Save 100% on your flight
Price was $891, price is now $569 per person
$569
per person
Dec 9 - Dec 13
found 14 hours 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 $1,695, price is now $959 per person
$959
per person
Dec 11 - Dec 15
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,029, price is now $691 per person
$691
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Spinnaker Inn of Naples

Spinnaker Inn of Naples

2 out of 5
Price was $825, price is now $592 per person
$592
per person
Dec 9 - Dec 13
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Truckland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,073, price is now $681 per person
$681
per person
Nov 14 - Nov 19
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 $2,053, price is now $1,187 per person
$1,187
per person
Dec 1 - Dec 8
found 13 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,534, price is now $918 per person
$918
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,378, price is now $879 per person
$879
per person
Dec 17 - Dec 22
found 16 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)

Top Flight Deals

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

Frontier Airlines
Sat, Jan 23 - Sun, Jan 24
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 Sat, Jan 23 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Sun, Jan 24, priced at $134 found 3 hours ago
Frontier Airlines
Tue, Nov 24 - Sun, Dec 6
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$140 Roundtrip, found 1 hour ago
$140
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Nov 24 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Dec 6, priced at $140 found 1 hour ago
Breeze Airways
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$173 Roundtrip, found 1 hour ago
$173
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Feb 6, priced at $173 found 1 hour ago
Frontier Airlines
Sun, Nov 15 - Sat, Dec 5
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$183 Roundtrip, found 4 hours ago
$183
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Nov 15 from Hopkins Intl. to Southwest Florida Intl., returning Sat, Dec 5, priced at $183 found 4 hours ago