Estero Island Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Estero Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Edison Beach House
Save 100% on your flight
Price was $700, price is now $428 per person
$428
per person
Nov 16 - Nov 20
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, 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.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was $1,975, price is now $919 per person
$919
per person
Nov 16 - Nov 20
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
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. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $926, price is now $538 per person
$538
per person
Nov 16 - Nov 20
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
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 located nearby.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $1,022, price is now $615 per person
$615
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Fort Myers (RSW)
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 reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
Hyatt Place Fort Myers/at The Forum
The Forum
Price was $1,053, price is now $666 per person
$666
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,363, price is now $902 per person
$902
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Fort Myers (RSW)
Stay at this 4-star eco-certified aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
Don't see what you're looking for?
See all available trips from Columbus to Estero Island
View all tripsTop Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
4.42 km from city center
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
4.17 km from city center
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 ...
Pink Shell Beach Resort and Marina
275 Estero Blvd, Fort Myers Beach, FL
5.85 km from city center
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 ...
Edison Beach House
830 Estero Blvd., Fort Myers Beach, FL
4.89 km from city center
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and ...
The Lighthouse Resort Inn & Suites
1051 5th St, Fort Myers Beach, FL
4.56 km from city center
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular ...
DiamondHead Beach Resort
2000 Estero Blvd, Fort Myers Beach, FL
3.7 km from city center
Stay at this 3.5-star beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
Casa Playa Beach Resort
510 Estero Blvd, Fort Myers Beach, FL
5.45 km from city center
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial ...
Best Western Plus Beach Resort
684 Estero Boulevard, Fort Myers Beach, FL
5.16 km from city center
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Key West Express and Lynn Hall Memorial ...
GullWing Beach Resort
6620 Estero Blvd, Fort Myers Beach, FL
1.81 km from city center
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita ...
Pointe Estero Beach Resort
6640 Estero Blvd, Fort Myers Beach, FL
1.85 km from city center
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free parking, a beach locale, and a garden. Popular attractions Key West Express and Bonita Springs ...
Matanzas Inn Bayside Resort and Marina
414 Crescent Street, Fort Myers Beach, FL
4.63 km from city center
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 ...
Harbour House At The Inn
450 Old San Carlos Blvd, Fort Myers Beach, FL
4.73 km from city center
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, a marina, and a business center. Our guests praise the clean rooms in our reviews. Popular attractions ...
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, Dec 8 - Thu, Dec 11
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Thu, Oct 30 - Fri, Oct 31
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Tue, Oct 7 - Sat, Oct 11
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Sun, Oct 12 - Thu, Oct 16
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Thu, Oct 2 - Sun, Oct 12
YYZ
Pearson Intl.
RSW
Southwest Florida Intl.
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago