Villas Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Villas Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Fort Myers Central
Save 100% on your flight
Price was $389, price is now $232 per person
$232
per person
Jan 24 - Jan 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
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 rooms in our reviews. Popular attractions Edison Mall and Vietnam War Memorial are located nearby.
Matanzas Inn Bayside Resort and Marina
Price was $904, price is now $432 per person
$432
per person
Jan 24 - Jan 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star 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 Times Square are located nearby.
Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
Price was $589, price is now $330 per person
$330
per person
Jan 24 - Jan 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Home2 Suites by Hilton Fort Myers Airport
Save 100% on your flight
Price was $634, price is now $373 per person
$373
per person
Jan 24 - Jan 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions JetBlue Park at Fenway South and Hertz Arena are located nearby.
South Seas Resort
Save 100% on your flight
Price was $1,304, price is now $809 per person
$809
per person
Dec 15 - Dec 20
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Fort Myers (RSW)
Stay at this 3.5-star beach resort in Captiva. Enjoy 3 outdoor pools, 6 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.
Hampton Inn & Suites Fort Myers-Estero/FGCU
Save 100% on your flight
Price was $583, price is now $375 per person
$375
per person
Jan 24 - Jan 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hertz Arena and Coconut Point Mall are located nearby.
Top Hotel Deals
Hilton Garden Inn Ft Myers
12600 University Dr, Fort Myers, FL
1.79 km from Villas
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 ...
Doubletree by Hilton Fort Myers at Bell Tower Shops
13051 Bell Tower Drive, Fort Myers, FL
0.11 km from Villas
Stay at this 4-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral
7090 Cypress Terrace, Fort Myers, FL
1 km from Villas
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Homewood Suites by Hilton - Fort Myers
5255 Big Pine Way, Fort Myers, FL
0.2 km from Villas
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 in our reviews. ...
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
13.84 km from Villas
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 ...
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
13.79 km from Villas
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
16.18 km from Villas
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 ...
Pink Shell Beach Resort and Marina
275 Estero Blvd, Fort Myers Beach, FL
13.77 km from Villas
Stay at this 4-star beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
Sanibel Island Beach Resort
1231 Middle Gulf Dr, Sanibel, FL
21.83 km from Villas
Stay at this 3-star beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
Baymont by Wyndham Fort Myers Central
4850 S Cleveland Ave, Fort Myers, FL
4.46 km from Villas
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 ...
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr, Fort Myers, FL
15.72 km from Villas
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 ...
The Perry Hotel Naples
12155 Tamiami Trail N, Naples, FL
30.64 km from Villas
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 ...
LaPlaya Beach & Golf Resort - A Noble House Resort
9891 Gulf Shore Dr, Naples, FL
32.46 km from Villas
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. ...
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.
Fri, Jan 30 - Mon, Feb 2
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Sat, Jan 3 - Sat, Jan 24
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$92 Roundtrip, found 3 days ago
$92
Roundtrip
found 3 days ago
Sat, Jan 10 - Sat, Jan 17
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Wed, Dec 31 - Thu, Jan 8
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Fri, Dec 5 - Wed, Dec 10
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 7 hours ago
$127
Roundtrip
found 7 hours ago