Downtown Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Landing Fort Myers Near Highland Pines
Daniels Corridor
$582
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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
Mariners Boathouse by Coolvacay
South Island
$722
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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
Matanzas Inn Bayside Resort and Marina
$765
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
THE Palmview AND Sandpiper Inns
Mid Island
$695
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this motel in Sanibel. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.
Landing Furnished Apartments minutes from Downtown Fort Myers
Hancock
$730
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this apartment in North Fort Myers. Enjoy an outdoor pool, a fitness center, and an in-room coffeemaker. Popular attractions Art of the Olympians Museum and Caloosa Sound Amphitheater are located nearby.
Windward Passage Resort
$620
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park are located nearby.
Wonderful view of the ocean
Reviewed on Sep 15, 2026
Top Hotel Deals
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 ...
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 ...
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 ...
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 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 ...
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 Delnor-Wiggins Pass State Park and Vanderbilt ...
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. ...
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 ...
Compass by Margaritaville Hotel Naples
4805 Tamiami Trl N Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise 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 ...
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the ...
Fairways Inn of Naples
103 Palm River Blvd Naples FL
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
Book a stay at this business-friendly hotel in Cape Coral. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Naples Bay Resort & Marina
1500 Fifth Ave S Naples FL
Book a stay at this spa hotel in Naples. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 7 - Wed, Oct 14
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$189
Roundtrip
found 4 days ago
Thu, Oct 1 - Thu, Oct 8
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$201
Roundtrip
found 6 days ago
Tue, Oct 6 - Tue, Oct 20
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$219
Roundtrip
found 2 days ago
Sun, Mar 14 - Fri, Mar 19
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$227
Roundtrip
found 2 days ago
Mon, Nov 9 - Tue, Nov 17
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$269
Roundtrip
found 9 hours ago
Best points of interest in Bonita Springs
- Riverside Park Vacations
- Sugarshack Downtown Vacations
- Bonita Springs Historical Society Vacations
- Key West Express Vacations
- Naples Beach Vacations
- Vanderbilt Beach Vacations
- Fifth Avenue South Vacations
- Florida Gulf Coast University Vacations
- JetBlue Park at Fenway South Vacations
- Hertz Arena Vacations
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