Search Deals onDowntown Vacation Packages
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites
Save 100% on your flight
Price was $600, price is now $410 per person
$410
per person
Dec 6 - Dec 12
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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,065, price is now $681 per person
$681
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 4-star 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.
Hyatt Place Fort Myers/at The Forum
The Forum
Price was $696, price is now $472 per person
$472
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip 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.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,191, price is now $829 per person
$829
per person
Dec 18 - Dec 22
found 10 hours 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.
Edison Beach House
Price was $1,193, price is now $830 per person
$830
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip 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
Save 100% on your flight
Price was $1,072, price is now $753 per person
$753
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Inn on Fifth
Old Naples
Save 100% on your flight
Price was $1,215, price is now $856 per person
$856
per person
Dec 18 - Dec 22
found 10 hours ago
Roundtrip flight included
Hartford (BDL) 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
Old Naples
Save 100% on your flight
Price was $1,451, price is now $1,025 per person
$1,025
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip 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.
3-4 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Downtown
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S, Naples, FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
Stay at this 4.5-star luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
Stay at this 4-star 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 ...
Save an average of 15% on thousands of hotels when you're signed in
Baymont by Wyndham Fort Myers Central
4850 S Cleveland Ave, Fort Myers, FL
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 and the clean ...
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent ...
Hyatt Vacation Club at Coconut Cove, Bonita Springs
11800 Coconut Cove Drive, Bonita Springs, FL
Stay at this 4-star golf aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita ...
Hilton Naples
5111 Tamiami Trl N, Naples, FL
Stay at this 4-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hilton Garden Inn Ft Myers
12600 University Dr, Fort Myers, FL
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 ...
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.
Sat, Jan 10 - Wed, Jan 21
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$100 Roundtrip, found 22 hours ago
$100
Roundtrip
found 22 hours ago
Wed, Jan 14 - Wed, Jan 21
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Mon, Dec 15 - Mon, Dec 22
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Mon, Dec 15 - Wed, Dec 24
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$116 Roundtrip, found 9 hours ago
$116
Roundtrip
found 9 hours ago
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- Barefoot Beach Vacations
- Vanderbilt Beach Vacations
- Coconut Point Mall Vacations