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 $520, price is now $380 per person
$380
per person
Sep 3 - Sep 8
found 8 hours ago
Roundtrip 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 Edison and Ford Winter Estates and The Ranch Concert Hall & Saloon are located nearby.
A Wave From it All
Siesta Isle
Price was $2,735, price is now $1,895 per person
$1,895
per person
Sep 6 - Sep 12
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this vacation home in Fort Myers Beach. Enjoy free WiFi, free parking, and 6 beach bars. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Landing Fort Myers - Eastwood Village
Eastwood Village
Price was $846, price is now $642 per person
$642
per person
Sep 6 - Sep 12
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury aparthotel in Fort Myers. Enjoy free WiFi, free parking, and 2 outdoor pickleball courts. Popular attractions Edison and Ford Winter Estates and Calusa Nature Center and Planetarium are located nearby.
Casa Tiki
Hancock
Price was $680, price is now $523 per person
$523
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this vacation home in Cape Coral. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Edison and Ford Winter Estates and Four Mile Cove Ecological Preserve are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,912, price is now $994 per person
$994
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this 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 Delnor-Wiggins Pass State Park are located nearby.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Save 100% on your flight
Price was $1,066, price is now $758 per person
$758
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this aparthotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
Gulfcoast Inn Naples
Moorings
Price was $670, price is now $502 per person
$502
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and 3 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Marco Beach Ocean Suites
South End
Save 100% on your flight
Price was $2,340, price is now $1,761 per person
$1,761
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Fort Myers (RSW)
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions South Marco Beach and Marco 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
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 ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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. ...
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 ...
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. ...
The Perry Hotel Naples
12155 Tamiami Trail N Naples FL
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass ...
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.
Wed, Sep 30 - Wed, Oct 7
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$88 Roundtrip, found 6 hours ago
$88
Roundtrip
found 6 hours ago
Wed, Jan 13 - Sat, Jan 16
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Sun, Aug 30 - Fri, Sep 18
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$178 Roundtrip, found 3 days ago
$178
Roundtrip
found 3 days ago
Tue, Sep 15 - Tue, Oct 6
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$182 Roundtrip, found 3 hours ago
$182
Roundtrip
found 3 hours ago
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