Estero Island Vacation Packages for 2026

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Top Hotel Deals

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
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

3.5 out of 5
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 Estero Boulevard ...
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

4 out of 5
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

3 out of 5
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

3.5 out of 5
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 ...
Best Western Plus Beach Resort

Best Western Plus Beach Resort

2.5 out of 5
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 ...
Edison Beach House

Edison Beach House

3.5 out of 5
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

3 out of 5
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 Estero Boulevard ...
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
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 Estero ...
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
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 ...
Pointe Estero Beach Resort

Pointe Estero Beach Resort

2 out of 5
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 Estero Boulevard ...
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
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 Estero Boulevard ...
Flamingo Inn

Flamingo Inn

3 out of 5
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

3 out of 5
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.

Frontier Airlines
Mon, Aug 17 - Thu, Aug 20
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 2 hours ago
$127
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Aug 17 from Hopkins Intl. to Southwest Florida Intl., returning Thu, Aug 20, priced at $127 found 2 hours ago
JetBlue Airways
Tue, Sep 22 - Sat, Sep 26
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 22 from Logan Intl. to Southwest Florida Intl., returning Sat, Sep 26, priced at $177 found 3 days ago
Delta
Sat, Sep 19 - Tue, Sep 22
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Sep 19 from Logan Intl. to Southwest Florida Intl., returning Tue, Sep 22, priced at $177 found 5 days ago
American Airlines
Tue, Sep 22 - Sat, Sep 26
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 22 from Logan Intl. to Southwest Florida Intl., returning Sat, Sep 26, priced at $197 found 3 days ago
Sun Country Airlines
Tue, Sep 29 - Tue, Oct 6
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Tue, Sep 29 from Minneapolis - St. Paul Intl. to Southwest Florida Intl., returning Tue, Oct 6, priced at $207 found 5 days ago