Find all hotels by Highgate Independent in Fleming Key, FL from $159

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Compare rooms and suites by Highgate Independent in Fleming Key with rates, reviews, and availability. Most hotels are fully refundable.

"We really enjoyed our stay and had everything we needed. The room was clean and the staff was friendly."

$352 total

includes taxes & fees

Jun 4 - Jun 5

3 outdoor pools, pool umbrellas, sun loungers

"Wonderful staff, food and amenities. Location was right near harbor, restaurants and pools were first class. Pleasantly surprised at how perfect this resort was. The rooms are modern and well equipped, even has a fridge."

$373 total

includes taxes & fees

Jun 4 - Jun 5

"Nice resort liked that there was a restaurant on site. All staff was very friendly and helpful. Loved my stay."

$369 total

includes taxes & fees

Jun 19 - Jun 20

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"Employees were great and the property was clean. "

$230 total

includes taxes & fees

May 22 - May 23

Ocean View Double Queen | Premium bedding, individually furnished, desk, laptop workspace

"The best. Love it "

$230 total

includes taxes & fees

May 22 - May 23

Highgate Independent Fleming Key Hotel Guide

Some globe-trotters choose hotels based on location, but others book by name. And thanks to Expedia you don’t have to pick. It is why we offer such an expansive range of Highgate Independent hotels in Fleming Key, Key West. Known for well-appointed rooms and friendly, personalized service, each of the top Highgate Independent Fleming Key hotels guarantees an unparalleled level of comfort and quality.

You’ll find best-in-class amenities like clean rooms and quiet atmospheres, and some Fleming Key Highgate Independent locations may even offer extra little benefits and discounts for frequent travelers.

Recent reviews of Fleming Key hotels
Expedia verified reviews

Winslow's Bungalows - Key West Historic Inns

5/5 Excellent

"Winslow's Bungalows were a much needed respite from the "real world." I love the history of the inns, and this is what originally made me book this location. The location is very walkable, and we walked down the street to a local bike rental to rent bikes. We were then able to bike all over the historic district. The reviews showed me that Winslow's had an amazing continental breakfast, and this was very much the truth. This was absolutely the best breakfast that I have had that was provided at no extra charge. Another great perk is the onsite bar. It was nice to be able to get an afternoon beverage right there where we were staying. The staff were wonderful, and super friendly. The room was super clean, the beds were super comfy, and we were super comfortable during our stay."

A verified traveler stayed at Winslow's Bungalows - Key West Historic Inns

Posted 8 hours ago