Estero Island Vacation Packages for 2026
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.
The Perry Hotel Naples
Save 100% on your flight
Price was $955, price is now $545 per person
$545
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) 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 Barefoot Beach are located nearby.
Innovation Hotel
Save 100% on your flight
Price was $2,124, price is now $1,236 per person
$1,236
per person
Feb 19 - Feb 24
found 6 hours ago
Roundtrip non-stop flight included
Eau Claire (EAU) to Fort Myers (RSW)
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 in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,980, price is now $1,778 per person
$1,778
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Providence (PVD) 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 Barefoot Beach are located nearby.
Comfort Inn & Suites
Save 100% on your flight
Price was $952, price is now $610 per person
$610
per person
Feb 19 - Feb 24
found 6 hours ago
Roundtrip non-stop flight included
Eau Claire (EAU) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
Home2 Suites Naples I-75 Pine Ridge Road, FL
Save 100% on your flight
Price was $1,472, price is now $991 per person
$991
per person
Feb 19 - Feb 24
found 6 hours ago
Roundtrip non-stop flight included
Eau Claire (EAU) to Fort Myers (RSW)
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 in our reviews. Popular attractions Naples Zoo at Caribbean Gardens and Vanderbilt Beach are located nearby.
Edison Beach House
Save 100% on your flight
Price was $2,066, price is now $1,446 per person
$1,446
per person
Feb 19 - Feb 24
found 6 hours ago
Roundtrip non-stop flight included
Eau Claire (EAU) to Fort Myers (RSW)
Book a stay at this 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.
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
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
4.17 km from city center
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent ...
DiamondHead Beach Resort
2000 Estero Blvd Fort Myers Beach FL
3.7 km from city center
Book a stay at this 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 ...
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
5.85 km from city center
Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
Matanzas Inn Bayside Resort and Marina
414 Crescent Street Fort Myers Beach FL
4.63 km from city center
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 ...
The Lighthouse Resort Inn & Suites
1051 5th St Fort Myers Beach FL
4.56 km from city center
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Edison Beach House
830 Estero Blvd. Fort Myers Beach FL
4.89 km from city center
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and ...
GullWing Beach Resort
6620 Estero Blvd Fort Myers Beach FL
1.81 km from city center
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita ...
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 ...
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 ...
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 ...
Harbour House At The Inn
450 Old San Carlos Blvd Fort Myers Beach FL
4.73 km from city center
Stay at this 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.
Sat, Jan 10 - Sat, Jan 17
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Sun, Jan 11 - Tue, Jan 13
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Fri, Jan 23 - Fri, Feb 6
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$137 Roundtrip, found 20 hours ago
$137
Roundtrip
found 20 hours ago
Thu, Jan 22 - Tue, Feb 10
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$157 Roundtrip, found 20 hours ago
$157
Roundtrip
found 20 hours ago
Sun, Mar 22 - Sat, Mar 28
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago