Estero Island Vacation Packages for 2026
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Estero Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral
Price was $962, price is now $646 per person
$646
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) 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 clean rooms in our reviews. Popular attractions Edison Mall and Broadway Palm Dinner Theatre are located nearby.
Windward Passage Resort
Price was $2,407, price is now $1,694 per person
$1,694
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park are located nearby.
The Bay Inn at Lani Kai
Price was $1,525, price is now $1,084 per person
$1,084
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and 6 bars/lounges. Popular attractions Key West Express and Crescent Beach Family Park are located nearby.
They charged me to park at a place where I was staying didn’t like that. They charged me each a day for towels and water, their pool is small and can’t have drinks in it, not allowed your own alcohol or coolers on the beach. I will not stay here again nor will I recommend it to anyone . Too many hidden fees.
Reviewed on Nov 14, 2026
Landing Apartments Fort Myers near Eastwood Village
Price was $1,735, price is now $1,244 per person
$1,244
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Stay at this apartment in Fort Myers. Enjoy in-room washers/dryers, an in-room coffeemaker, and air conditioning. Popular attractions JetBlue Park at Fenway South and Calusa Nature Center and Planetarium are located nearby.
I've stayed at the property twice, and both experiences were good. The apartments are newer and are clean and well maintained. The pool and fitness center are nice amenities. Communication with the host was excellent.
Reviewed on Nov 12, 2026
Lani Kai Beachfront Resort
Price was $1,763, price is now $1,304 per person
$1,304
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Crescent Beach Family Park are located nearby.
Landing Apartments Fort Myers near Olympia Pointe
Price was $1,542, price is now $1,154 per person
$1,154
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Book a stay at this business-friendly aparthotel in Fort Myers. Enjoy free WiFi, free parking, and a fitness center. Popular attractions JetBlue Park at Fenway South and Topgolf are located nearby.
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Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
3.76 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
3.51 km from city center
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Crescent Beach ...
The Lighthouse Resort Inn & Suites
1051 5th St Fort Myers Beach FL
3.89 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. ...
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
5.17 km from city center
Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the ...
DiamondHead Beach Resort
2000 Estero Blvd Fort Myers Beach FL
3.02 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 Bay Inn at Lani Kai
1401 Estero Blvd Fort Myers Beach FL
3.55 km from city center
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and 6 bars/lounges. Popular attractions Key West Express and Crescent Beach ...
Edison Beach House
830 Estero Blvd. Fort Myers Beach FL
4.22 km from city center
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Matanzas Inn Bayside Resort and Marina
414 Crescent Street Fort Myers Beach FL
3.94 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 ...
Pointe Estero Beach Resort
6640 Estero Blvd Fort Myers Beach FL
2.6 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 ...
Best Western Plus Beach Resort
684 Estero Boulevard Fort Myers Beach FL
4.49 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
2.56 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 ...
Casa Playa Beach Resort
510 Estero Blvd Fort Myers Beach FL
4.78 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 ...
Flamingo Inn
6090 Estero Blvd Fort Myers Beach FL
1.95 km from city center
Stay at this apartment in Fort Myers Beach. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the property condition in our reviews. Popular ...
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.
Thu, Jan 21 - Tue, Jan 26
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Mon, Jan 11 - Fri, Jan 22
TTN
Mercer
RSW
Southwest Florida Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Thu, Jan 21 - Tue, Jan 26
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Sun, Jan 17 - Sun, Jan 24
MKE
General Mitchell Intl.
RSW
Southwest Florida Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Sat, Feb 20 - Sat, Feb 27
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago