
Cudjoe Key Holidays
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Top Flight + Hotel Deals in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.


Hyatt Vacation Club at Windward Pointe, Key West
per person
7 Oct - 10 Oct
found 23 hours ago
Return direct flight included
New York (JFK) to Key West (EYW)
9.6/10 Exceptional! (1,024 reviews)
We enjoyed our stay very much and will be staying here again in the near future. Everything about it was very nice with beautiful views of the property.
Reviewed on 4 Aug 2025

Orchid Key Inn - Adults Only
Old Town Key West
per person
7 Oct - 10 Oct
found 23 hours ago
Return direct flight included
New York (JFK) to Key West (EYW)
9.8/10 Exceptional! (1,011 reviews)
This hotel is small and intimate. Everything was super clean and comfortable. Staff was nice. Very relaxing atmosphere. I would stay here again.
Reviewed on 6 Aug 2025

Almond Tree Inn Hotel - Adults Only
Old Town Key West
per person
7 Oct - 10 Oct
found 23 hours ago
Return direct flight included
New York (JFK) to Key West (EYW)
10/10 Exceptional! (1,009 reviews)
Really close to Duvall but still quiet. Great Cuban restaurant and dessert bar just down the street.
Reviewed on 6 Aug 2025

Southernmost Beach Resort and Guesthouses
Old Town Key West
per person
7 Oct - 10 Oct
found 23 hours ago
Return direct flight included
New York (JFK) to Key West (EYW)
8.6/10 Excellent! (2,668 reviews)
Great spot for my teenager. Easy parking. Very clean grounds . Would book here again
Reviewed on 6 Aug 2025
Top hotels in Cudjoe Key

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
The price is €224 per night from 27 Aug to 28 Aug
€224
27 Aug - 28 Aug
includes taxes & fees
8.4/10 Very Good! (144 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
Reviewed on 20 Jul 2025

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is €173 per night from 18 Aug to 19 Aug
€173
18 Aug - 19 Aug
includes taxes & fees
8.4/10 Very Good! (1,425 reviews)
"Great property. Clean. Great pool."
Reviewed on 4 Aug 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is €158 per night from 7 Sept to 8 Sept
€158
7 Sept - 8 Sept
includes taxes & fees
7.6/10 Good! (1,525 reviews)
"Just five minutes from the airport and the shuttle will take you into the Mallory Square area every hour. 10:30 is last shuttle back. Hopefully in the near future all the restaurants will be open and lobby bar but I didn’t have use any and didn’t know they weren’t done with renovations. Should have ..."
Reviewed on 5 Aug 2025
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.
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