Search Deals onDowntown Vacation Packages
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Stay Inn & Suites
Winkler
Price was $616, price is now $450 per person
$450
per person
Oct 1 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Fort Myers. Enjoy free WiFi, free parking, and room service. Popular attractions The Ranch Concert Hall & Saloon and Edison Mall are located nearby.
Landing Furnished Apartments - Naples, FL
Price was $1,441, price is now $1,075 per person
$1,075
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Myers (RSW)
Book a stay at this business-friendly apartment in Naples. Enjoy free WiFi, a rooftop terrace, and a fitness center. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,776, price is now $1,155 per person
$1,155
per person
Oct 2 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The Bay Inn at Lani Kai
Save 100% on your flight
Price was $1,152, price is now $753 per person
$753
per person
Oct 2 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and 6 bars/lounges. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,706, price is now $1,148 per person
$1,148
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Save 100% on your flight
Price was $809, price is now $562 per person
$562
per person
Oct 15 - Oct 19
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this spa hotel in Punta Gorda. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Price was $690, price is now $494 per person
$494
per person
Oct 15 - Oct 19
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $1,252, price is now $928 per person
$928
per person
Oct 2 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 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 Estero Boulevard Beach 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
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Estero Boulevard ...
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 ...
Margaritaville Beach Resort Fort Myers
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Great Wolf Lodge Naples
3900 City Gate Blvd N. Naples FL
Book a stay at this family-friendly hotel in Naples. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Popular attractions Paradise Coast Sports Compex and ...
Marriott Sanibel Harbour Resort & Spa
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 ...
Sanibel Island Beach Resort
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. ...
Hyatt House Naples/5th Avenue
1345 5th Avenue South Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
Hyatt Vacation Club at Coconut Cove, Bonita Springs
11800 Coconut Cove Drive Bonita Springs FL
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 ...
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.
Fri, Sep 25 - Fri, Oct 9
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Mon, Nov 23 - Thu, Dec 3
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Fri, Sep 11 - Sun, Sep 13
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$187 Roundtrip, found 3 hours ago
$187
Roundtrip
found 3 hours ago
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