Cudjoe Key Trip

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Top Cudjoe Key Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₹156,678, price is now ₹109,195 per person
₹109,195
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.4/10 Exceptional! (1,491 reviews)
The area was very colourful and convenient to be around.

Reviewed on 17 Nov 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was ₹309,690, price is now ₹177,925 per person
₹177,925
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Staff super friendly and welcoming and helpful, room ready

Reviewed on 16 Nov 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹157,017, price is now ₹109,354 per person
₹109,354
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.8/10 Exceptional! (1,775 reviews)
Staff were all wonderful, especially Henry he was extremely helpful and had a great personality!

Reviewed on 18 Nov 2025

72 Park - Miami Beach by Nomada

72 Park - Miami Beach by Nomada

4.5 out of 5
North Beach
Price was ₹195,346, price is now ₹140,350 per person
₹140,350
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
8.8/10 Excellent! (64 reviews)
Room was so well prepared VIEW WAS AMAZING, STAFF was COURTEOUS and ATTENTIVE

Reviewed on 16 Nov 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was ₹169,890, price is now ₹127,614 per person
₹127,614
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
17.2/10 Exceptional! (385 reviews)
Wonderful Stay every time I come to Miami I will be there just to stay at this hotel.

Reviewed on 18 Nov 2025

Top hotels in Cudjoe Key

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is ₹11,328 per night from 19 Nov to 20 Nov
₹11,328
₹17,231 total
19 Nov - 20 Nov
includes taxes & fees
8.6/10 Excellent! (1,680 reviews)
Staff was horrible on directions to room. We had to give directions to 4 different sets of new guests as well as getting lost ourselves. Place was great. Nice location.

Reviewed on 13 Nov 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is ₹6,861 per night from 10 Dec to 11 Dec
₹6,861
₹12,704 total
10 Dec - 11 Dec
includes taxes & fees
7.8/10 Good! (1,693 reviews)
What a fun little resort. The amenities are fabulous! They have live music. We heard Ike Kanakanaui. He was REALLY good!

Reviewed on 14 Nov 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is ₹12,579 per night from 8 Dec to 9 Dec
₹12,579
₹19,485 total
8 Dec - 9 Dec
includes taxes & fees
8.8/10 Excellent! (1,734 reviews)
Very clean and private. Make sure you are aware of resort fees and parking fees. In my opinion, there is no need to rent a car. The property provides a shuttle service that takes you to Key West. We will definitely stay here again and not rent a car. The marina is lovely. It is not “beach side” but ...

Reviewed on 10 Nov 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,778 properties in Cudjoe Key
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.