Cudjoe Key Mountain Vacations
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Flight and Mountain hotel deals in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive
Old Town Key West
CA $2,714
per person
Oct 10 - Oct 17
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!
Reviewed on Aug 16, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,544
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
1 Hotel South Beach
South Beach
CA $3,424
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
Everything about this hotel is AMAZING especially the staff! I definitely recommend this hotel, I can’t wait to come back with my kiddos!
Reviewed on Aug 16, 2026
5* Mountain holidays in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
Andaz Miami Beach Resort & Spa
Mid Beach
CA $1,326
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9/10 Wonderful! (354 reviews)
We had such a wonderful stay! The resort was beautiful, clean, cozy, and very comfortable. What really stood out was how welcoming everyone made us feel. The staff truly went above and beyond to make sure we were comfortable and had everything we needed throughout our stay. You could tell they genuinely cared about making our experience special. We really enjoyed our time here and would definitely recommend it!
Reviewed on Aug 16, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,544
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
1 Hotel South Beach
South Beach
CA $3,424
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
Everything about this hotel is AMAZING especially the staff! I definitely recommend this hotel, I can’t wait to come back with my kiddos!
Reviewed on Aug 16, 2026
3 Night Mountain holidays in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $9,510
per person
Oct 29 - Nov 1
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Bentley Hotel South Beach
South Beach
CA $1,542
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Miami (MIA)
9.4/10 Exceptional! (1,036 reviews)
Everything was great or better. Room was very nice and what we hoped for. Excellent location. Perfect value. Staff and customer service were stellar, especially Reynold and Axel, exemplary hospitality professionals.
Reviewed on Aug 16, 2026
4 Night Mountain holidays in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive
Old Town Key West
CA $2,381
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!
Reviewed on Aug 16, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $10,113
per person
Oct 18 - Oct 22
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
The Key West Hotel
Key West Historic District
CA $4,711
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!
Reviewed on Jul 27, 2026
Things to do
Discover US East Coast Self Guided Audio Tour
CA $204
per traveller
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
CA $238
per adult
Private Sandbar Adventure in Key West Backcountry
CA $772
per traveller
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
