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.
Courtyard by Marriott Fort Myers Cape Coral
Save 100% on your flight
Price was $490, price is now $302 per person
$302
per person
May 2 - May 8
found 13 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Edison Mall and Fort Myers Country Club are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $4,625, price is now $2,683 per person
$2,683
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $1,128, price is now $669 per person
$669
per person
May 2 - May 8
found 13 hours ago
Roundtrip non-stop 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 Times Square are located nearby.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $1,066, price is now $655 per person
$655
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this 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 Edison Mall and Barbara B Mann Hall are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $938, price is now $579 per person
$579
per person
May 2 - May 8
found 13 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this golf 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.
The Perry Hotel Naples
Save 100% on your flight
Price was $2,683, price is now $1,710 per person
$1,710
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
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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 ...
The Lighthouse Resort Inn & Suites
1051 5th St Fort Myers Beach FL
4.57 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. ...
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 ...
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 ...
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 ...
Matanzas Inn Bayside Resort and Marina
414 Crescent Street Fort Myers Beach FL
4.64 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 ...
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 ...
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 ...
Carribean Beach Club
7600 Estero Blvd Fort Myers Beach FL
3.07 km from city center
Stay at this condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita Springs Public Beach ...
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, May 2 - Sat, May 16
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
Sun, Mar 1 - Wed, Mar 4
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$101 Roundtrip, found 4 days ago
$101
Roundtrip
found 4 days ago
Mon, Apr 27 - Wed, May 13
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Mon, Apr 27 - Wed, May 13
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Sat, May 2 - Sat, May 9
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago