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.
Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

Venice Island
$845
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this vacation home in Venice. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Venice Beach and Nokomis Beach are located nearby.
Inn at the Beach

Inn at the Beach

Venice Island
Save 100% on your flight
$1,036
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this hotel in Venice. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. Popular attractions Venice Beach and Nokomis Beach are located nearby.
We like the fact that the room is very clean. The staff is very nice. We have been there multiple times. It’s always been wonderful thank you.

Reviewed on Sep 28, 2026

Venice Beach Villas

Venice Beach Villas

Venice Island
$852
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly condo in Venice. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Venice Beach and Nokomis Beach are located nearby.
A very cute boutique hotel, has a lot of great amenities. I will say one issue I had was there was a lot of ants in the bathroom by the sink. Great for a couple of days, but I probably wouldn't say for longer than that.

Reviewed on Sep 25, 2026

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Margaritaville Beach Resort Fort Myers

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

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, 3 restaurants, and a beach locale. Popular attractions Key West Express and Crescent Beach ...
Pink Shell Beach Resort and Marina

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 a full-service spa. Our guests praise the breakfast and the ...
The Lighthouse Resort Inn & Suites

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. ...
DiamondHead Beach Resort

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 ...
Edison Beach House

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 breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Bay Inn at Lani Kai

The Bay Inn at Lani Kai

1401 Estero Blvd Fort Myers Beach FL
4.22 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 ...
Matanzas Inn Bayside Resort and Marina

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 ...
Best Western Plus Beach Resort

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 Estero Boulevard ...
Pointe Estero Beach Resort

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

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 ...
Windward Passage Resort

Windward Passage Resort

418 Estero Blvd Fort Myers Beach FL
5.61 km from city center
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 ...
Casa Playa Beach Resort

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 ...
Flamingo Inn

Flamingo Inn

6090 Estero Blvd Fort Myers Beach FL
1.24 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 ...
Harbour House At The Inn

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 ...
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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.

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