Estero Island Vacation Packages
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Top Estero Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
Price was CA $1,030, price is now CA $712 per person
CA $712
per person
Aug 14 - Aug 18
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (838 reviews)
The staff were very friendly, and the hotel is very clean.
Reviewed on Jun 10, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was CA $1,818, price is now CA $1,085 per person
CA $1,085
per person
Aug 14 - Aug 18
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,012 reviews)
We absolutely loved the little resort and already planning a trip back! 10/10!
Reviewed on Jun 14, 2026
Casa Ybel Resort
Mid Island
Price was CA $2,513, price is now CA $1,794 per person
CA $1,794
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
8.8/10 Excellent! (357 reviews)
Excellent place, great location, the ocen is just steps from the condo, nice pool for swim laps! will definitely return, thank you for having us.
Reviewed on Jun 11, 2026
Matanzas Inn Bayside Resort and Marina
Price was CA $1,566, price is now CA $1,118 per person
CA $1,118
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,012 reviews)
Very close to the beach, but far enough away to be quiet. Spacious room, great kitchenette.
Reviewed on Jun 8, 2026
Bellasera Resort
Old Naples
Price was CA $1,394, price is now CA $1,016 per person
CA $1,016
per person
Aug 14 - Aug 18
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (2,275 reviews)
Wow. Second year coming to this resort and even better second time round.
Great staff. Great pool area.
Bar and food/drinks were fantastic. Already looking forward to next year
Reviewed on Jun 12, 2026
Estero Island Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
The price is CA $279 per night from Jun 28 to Jun 29
CA $279
CA $381 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (2,205 reviews)
"I was very disappointed with the check-out experience. There was no porter service available to assist guests with their luggage when leaving it at the concierge desk. Furthermore, access to the room was disabled before 11:00 a.m., creating unnecessary inconvenience. The concierge desk is located ..."
Reviewed on Jun 14, 2026
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Jun 16 to Jun 17
CA $172
CA $223 total
Jun 16 - Jun 17
includes taxes & fees
9/10 Wonderful! (1,604 reviews)
"A great place on the Beach. Staff excellent, professional, courtesy, friendly and informative. Restaurants were fantastic, great food. Highly recommend."
Reviewed on Jun 13, 2026
The Lighthouse Resort Inn & Suites
1051 5th St Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Jun 17 to Jun 18
CA $182
CA $230 total
Jun 17 - Jun 18
includes taxes & fees
8.6/10 Excellent! (1,692 reviews)
"Worse place I ever stayed. I got a message the day before, the elevator wasn’t working. Ok.. I got there after driving under a heavy rain and they told me where to park. Finished my check in, went to my car get my luggage and realized I was at 3rd at the opposite side where I parked and had to carry ..."
Reviewed on Jun 12, 2026
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.
Stay near popular Estero Island attractions
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- Pet-Friendly Hotels in Mid Island
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- Barefoot Beach
- Bonita Springs Vacations
- Bowditch Point Park
- Bunche Beach
- Cape Coral Vacations
- Coconut Point Mall
- Delnor-Wiggins Pass State Park
- Eagle Ridge Golf Club
- Estero Vacations
- Florida Gulf Coast University
- Visit Mid Island
- Fort Myers Beach Vacations
- Visit Fort Myers Beach
- Golfview Golf and Racquet Club
- Hertz Arena
- Key West Express
- Legends Golf and Country Club
- Little Hickory Island Beach Park
- Lovers Key State Park Vacations
- Visit Lovers Key State Park
- Lynn Hall Memorial Park
- Mercato
- Naples Marina and Excursions
- Ostego Bay Marine Science Center
- Raptor Bay Golf Club
- San Carlos Golf Club
- San Carlos Island Vacations
- Sanibel Island Golf Club
- Sanibel Sea School
- Sanibel Vacations
- Six Mile Cypress Slough Preserve
- Southwest Florida Vacations
- Vanderbilt Beach
- Beach Vacation Packages Fort Myers Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
