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.
Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
Price was $613, price is now $351 per person
$351
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $642, price is now $371 per person
$371
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
South Seas Resort
Save 100% on your flight
Price was $1,417, price is now $838 per person
$838
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,110, price is now $661 per person
$661
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,618, price is now $984 per person
$984
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $661, price is now $409 per person
$409
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
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 Springs Public 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
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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, Feb 7 - Sat, Feb 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
Sat, Feb 7 - Sat, Feb 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Sat, Feb 7 - Sat, Feb 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$115 Roundtrip, found 4 days ago
$115
Roundtrip
found 4 days ago
Sat, Feb 28 - Fri, Mar 6
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Mon, Dec 8 - Wed, Dec 24
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago