Estero Island Vacation Packages
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Top Estero Island vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Matanzas Inn Bayside Resort and Marina
9.4/10 Exceptional! (1,004 reviews)
Oct 20 - Oct 24
4 night stay
Boston (BOS) to Fort Myers (RSW)
American Airlines • Roundtrip • Coach
Price was $642, price is now $503 per person
$503
per person
found 1 day ago
Very clean property and room. The sliding door on the bathroom was annoying because it was installed incorrectly and left a 4” gap for no privacy. The owner/manager was wonderful. She went above and beyond kind and accommodating. We would go back.
Reviewed on Sep 5, 2026
3.5-star property
GullWing Beach Resort
South Island
9.6/10 Exceptional! (968 reviews)
Nov 7 - Nov 14
7 night stay
Boston (BOS) to Fort Myers (RSW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,414, price is now $928 per person
$928
per person
found 1 day ago
Highly recommended, coastal by the sea, good for family outings.
Reviewed on Sep 5, 2026
3.0-star property
Flamingo Inn
Mid Island
8/10 Very Good! (1,022 reviews)
Nov 7 - Nov 14
7 night stay
Boston (BOS) to Fort Myers (RSW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $943, price is now $729 per person
$729
per person
found 1 day ago
Everything was great, quiet and perfect for the night, communication with the host was spot on. I will absolutely stay again
Reviewed on Aug 31, 2026
3.0-star property
The Wren
Mid Island
10/10 Exceptional! (2 reviews)
Nov 7 - Nov 14
7 night stay
Boston (BOS) to Fort Myers (RSW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,090, price is now $845 per person
$845
per person
found 1 day ago
Todo muy limpio muy espacioso perfecto para 8 personas muy cerca de la playa
Reviewed on Aug 11, 2026
Top rated hotels for your Estero Island vacation package
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Free Cancellation
Reserve now, pay when you stay
2.74 mi from city center
$192 nightly
The price is $214 total per night
$214 total
Sep 9 - Sep 10
Total with taxes and fees
At Margaritaville Beach Resort Fort Myers , guests enjoy a full-service spa, an outdoor pool, and a 24-hour gym. Valet parking is available for USD 35 per day. The front desk is staffed 24 hours a day to help with concierge services and dry cleaning/laundry. Other amenities at this beach hotel include free WiFi in public areas, a business center, and a terrace.
Pool
Spa
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Free Cancellation
Reserve now, pay when you stay
2.59 mi from city center
$151 nightly
The price is $169 total per night
$169 total
Sep 7 - Sep 8
Total with taxes and fees
Guests staying at Lani Kai Beachfront Resort enjoy an outdoor pool, a rooftop terrace, and free WiFi in public areas. Self parking is offered for USD 20.00 per night. The front desk is staffed 24 hours a day to help with securing valuables and luggage storage. Other amenities at this beach hotel include laundry facilities, a water dispenser, and a communal living room.
Pool
Free WiFi
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
3.63 mi from city center
$268 nightly
The price is $299 total per night
$299 total
Sep 29 - Sep 30
Total with taxes and fees
Pink Shell Beach Resort and Marina features a marina, a full-service spa, and 3 outdoor pools. You'll find limited parking. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Other amenities at this beach resort include a gym, a hot tub, and meeting rooms.
Pool
Hot Tub
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.
Things to do
Sunset Dolphin Cruise with Sanibel Lighthouse Views
$62
per adult
94% of travellers recommend
2.5-Hour Guided Group Kayak Tour on Big Hickory Pass
$55
per adult
Fort Myers Beach Sunset and Dolphin Watching Cruise
$70
per adult
100% of travellers recommend
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