Keewaydin Island Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Keewaydin Island
Price found within the past 48 hours. Click for updated prices.
Wyvern Hotel, an Ascend Collection Hotel
Downtown Punta Gorda
Price was CA $1,790, price is now CA $1,203 per person
CA $1,203
per person
Mar 24 - Mar 30
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Friendly Service, Beautiful room, within walking distance to restaurants and Punta Gorda Convention Center.
Reviewed on Feb 3, 2026
Landing Apartments Fort Myers near Olympia Pointe
Price was CA $1,294, price is now CA $887 per person
CA $887
per person
Apr 25 - May 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
10/10 Exceptional! (2 reviews)
This property is beautiful! We were thoroughly impressed with how nice our room was and how amazing the facilities were. The pool is incredible and made our stay that much better! We would definitely come back again and recommend to others.
Reviewed on Oct 7, 2025
Landing Apartments near North Fort Myers
Hancock
Price was CA $1,434, price is now CA $1,016 per person
CA $1,016
per person
Apr 17 - Apr 24
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (44 reviews)
There were a few issues with apartment but host stepped up and had them remedied immediately which was awesome. The place was perfect for our stay. Location is beautiful.
Reviewed on Jan 6, 2026
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View all trips5* Pet-friendly holidays in Keewaydin Island
Price found within the past 48 hours. Click for updated prices.
Sundial Beach Resort & Spa
Mid Island
Price was CA $2,065, price is now CA $1,757 per person
CA $1,757
per person
Mar 26 - Mar 29
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (2,581 reviews)
Very clean room, staff was very nice. All of the pools were clean and everything was very nice and well taken care of.
Reviewed on Jan 30, 2026
The Ritz-Carlton, Naples
Pelican Bay
Price was CA $7,370, price is now CA $6,839 per person
CA $6,839
per person
Apr 17 - Apr 24
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.2/10 Wonderful! (451 reviews)
Loved everything about this hotel, the people, the room, the amenities, all of it was top notch. No complaints whatsoever.
Reviewed on Jan 23, 2026
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Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was CA $1,736, price is now CA $1,250 per person
CA $1,250
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
The 2 room condo was huge& had everything you could ask for. The surroundings were beautiful.
Reviewed on Jan 30, 2026
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View all trips4 Night Pet-friendly holidays in Keewaydin Island
Price found within the past 48 hours. Click for updated prices.
South Seas Resort
Price was CA $2,587, price is now CA $1,679 per person
CA $1,679
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.4/10 Very Good! (1,001 reviews)
I'll preface this by saying that i had an incredible week and rhat Captiva is literal Paradise. My lodging however could use some work. The main office, gym facility, and retail establishments are excellent. Unfortunately my actual suite could use some work. While the facility was clean and had a spectacular view- the lodging was old and tired. Dirty elevators cheaply updated should have been a sign of things to come. Once inside the lodging I found cheap plastic flooring that flexed as you walked over uneven surface underneath. The walls were "updated" with textured wall covering the in areas was peeling. Baseboard looked as if a child did.the job. Poorly finished, improperly cut, and nailholes unfinished. Most things painted revraled many layers of old paint. Nights 1 and 2 were spent listening to the toilet by the bedroom run. Despite requesting it be remedied- it took speaking to the property manager on day 3 to get this accomplished. Ironically, the second toilet also broke and needed repair. Additionally- the water was only "warm" in the shower. Dining at the "resort" facilities is ridiculously expensive, so I ate better elsewhere for the same price. Lastly, there's no hospitality all week. You make your own bed, hang your towels, and if you want more- you drive to get them yourself.
Reviewed on Jan 18, 2026
Matanzas Inn Bayside Resort and Marina
Price was CA $1,419, price is now CA $1,027 per person
CA $1,027
per person
Apr 26 - Apr 30
found 8 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Very clean room with great view of estuary. Friendly staff. The only downside was that we were charged a $25 per day resort fee we were not expecting
Reviewed on Feb 7, 2026
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