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.
Windward Passage Resort
Save 100% on your flight
Price was $1,042, price is now $739 per person
$739
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 Estero Boulevard Beach are located nearby.
I loved this place it felt like home! Very clean and spacious. Everyone was kind, friendly, beach is within walking distance, pool on site, and overall great!
Reviewed on Aug 6, 2026
Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,169, price is now $759 per person
$759
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Buffalo (BUF) 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 Sanibel Island Lighthouse are located nearby.
Great place to stay. Always check your invoice because they had extra charges on my bill and place a huge hold on CC for deposit and takes time for return. It could be the bank too. They also charged me by error and refunded but still haven’t received after few days.the amenities were great and the beach! Also entrance with wood little bridge really scared us. I believe they fixed while we were there. Lots of bugs !! Maybe property should clean up trees and fumigate because we were bit by noseeums
Reviewed on Aug 5, 2026
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,252, price is now $830 per person
$830
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Buffalo (BUF) 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.
If you are disabled or handicapped DO NOT stay here. The management was rude and hurtful. We have stay there almost 30 years. Something bad is going on there.
Reviewed on Aug 4, 2026
The Perry Hotel Naples
Save 100% on your flight
Price was $1,455, price is now $967 per person
$967
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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 Delnor-Wiggins Pass State Park are located nearby.
Landing Furnished Apartments - Naples, FL
Save 100% on your flight
Price was $1,322, price is now $925 per person
$925
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.
Close by beach and 5th avenue
Reviewed on Jul 10, 2026
Mariners Boathouse by Coolvacay
South Island
Save 100% on your flight
Price was $1,331, price is now $970 per person
$970
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.
Pleasant stay. Staff friendly and attentive. Very relaxing stay. The view of the beach is a plus.
Reviewed on Aug 5, 2026
Top Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
21.39 km from Downtown
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 ...
Baymont by Wyndham Fort Myers Central
4850 S Cleveland Ave Fort Myers FL
29.28 km from Downtown
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 ...
Great Wolf Lodge Naples
3900 City Gate Blvd N. Naples FL
21.78 km from Downtown
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 ...
Hyatt House Naples/5th Avenue
1345 5th Avenue South Naples FL
22.17 km from Downtown
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
21.15 km from Downtown
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
28.46 km from Downtown
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
28.71 km from Downtown
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
7.02 km from Downtown
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 ...
Naples Bay Resort & Marina
1500 Fifth Ave S Naples FL
22.39 km from Downtown
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 ...
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S Naples FL
22.44 km from Downtown
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 ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
29.66 km from Downtown
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 ...
Compass by Margaritaville Hotel Naples
4805 Tamiami Trl N Naples FL
15.19 km from Downtown
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 ...
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
22.83 km from Downtown
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 ...
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.
Mon, Nov 2 - Wed, Nov 11
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Sat, Oct 3 - Tue, Oct 6
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Sun, Sep 27 - Mon, Oct 5
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$223 Roundtrip, found 1 hour ago
$223
Roundtrip
found 1 hour ago
Tue, Dec 8 - Tue, Dec 15
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Sat, Sep 19 - Sat, Sep 26
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago