
Florida Keys Adventure Vacations
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Flight and Adventure hotel deals in Florida Keys
Price found within the past 48 hours. Click for updated prices.

Tranquility Bay Beachfront Hotel and Resort
CA $1,565
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Miami (MIA)
8.8/10 Excellent! (1,009 reviews)
The room was clean and the pools were excellent! But everything else was just average, and I don't know that I'd say it was worth a $50/day resort fee (what does this cover? Why not just put it in the room rate?)
We stayed 4 nights and by the third night we had to ask to have someone come by and bring fresh towels. I'm used to seeing signs at hotels that state for environmental reasons they may only clean rooms every so often, but there was no such indication.
Our room was off at the edge of the resort, by the fitness room which meant every time someone came in the building, the whole building shook when the door slammed behind them. So much for getting a nice sleep-in on vacation because this started at 5 or 6 am.
I can definitely see the benefit to staying here with a larger group, families and friends staying in one of the villas. But as a couple, I probably wouldn't come back.
Reviewed on Sep 15, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
CA $1,781
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Miami (MIA)
9/10 Wonderful! (258 reviews)
We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting.
One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area.
The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere.
Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!
Reviewed on Sep 15, 2026



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Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
- 10 min walk from Duval Street
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (3,605 reviews)
"The property should have advertised that it was off season and there were amenities closed. The beach was closed the pool was closed. Those were two reasons we chose this resort. We also had a noise issue with the room and the front desk staff tried to give us ear plugs instead of trying to find ..."
Reviewed on Sep 16, 2026

Hawks Cay Resort
61 Hawks Cay Blvd Marathon FL
- 2 hours drive from Duval Street
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.2/10 Very good! (1,011 reviews)
"Beautiful resort"
Reviewed on Sep 15, 2026

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
- 3 hours drive from Duval Street
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
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

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend

Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $77
per adult
88% of travellers recommend

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
CA $109
per adult
94% of travellers recommend
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