Spend Christmas in Key West on Stock Island
Trade the cold for the marina. The Perry Hotel & Marina sits right on the water on Stock Island, the working-waterfront side of Key West, so your Christmas can start with coffee on the balcony and finish with dinner at Matt’s Stock Island Kitchen & Bar. Two waterfront pools and a shuttle into Old Town are there whenever you want them.
Holiday Events and Dining at The Perry
There’s plenty going on at the marina this December. Here’s where to start.
Key West Christmas Events and Holiday Lights
Key West goes all out for the holidays. Here’s what’s on, by date, all within roughly a 20 minute drive of The Perry. Check times with the organizers before you go.
See Key West all lit up on the Conch Tour Train's holiday night tours, running November 13 to December 9, 2026 (tour dates and times to be confirmed). It's about 3.5 to 4 miles, or 10 to 15 minutes by car, to the departure area.
Stroll the harbor after dark and take in the lights, November 25 to December 31, 2026. It's about 5 to 5.5 miles, or 15 to 20 minutes by car.
Browse the Holiday Village from 5 to 9 PM on Friday, December 4, 2026, then join the BeLighted Bike Ride at 8 PM. About 5.5 to 6 miles, or 15 to 20 minutes by car.
Grab a spot along the route for Key West's Hometown Holiday Parade on Saturday, December 5, 2026 (start time to be confirmed). Leave extra time for road closures. About 4 to 5 miles, or 15 to 20 minutes by car.
Head to the Historic Seaport on Saturday, December 12, 2026 for the Lighted Boat Parade. Festivities start at 6 PM and the parade rolls at 8 PM. About 5 to 5.5 miles, or 15 to 20 minutes by car.
Key West Hotel Rooms and Suites for Christmas
These are the four rooms we’d book for Christmas. Each has a private balcony, so pick the layout that suits your crew, and book direct to get the Insider Offer.
- 1 King Bed + Sleeper Sofa
- Sleeps 4
- 682 sq ft
Grand Suite
- 1 King Bed + Sofa
- Sleeps 4
- Private Balcony
Commodore Suite
- 2 Queen Beds
- Sleeps 4
- Private Balcony
Stock Island Double Queen
- 1 King Bed + Sleeper Sofa
- Sleeps 4
- Private Balcony
Saltwater Studio King
Planning Your Holiday Stay in Key West
Getting around
Our complimentary shuttle runs to Old Town, about 5 miles away, and the airport is about 3 miles from the hotel.
Check in and parking
Check-in is at 4 PM, check-out is at 11 AM, and self-parking is $29 per night plus tax.
Dogs welcome
Up to two dogs per room, at $75 per night for the first and $25 for the second.
Families and pools
Two waterfront pools, cabana rentals, suites with sleeper sofas and in-room massages.
Holiday Stay FAQs
Is The Perry close to downtown Key West and the holiday festivities?
We’re on Stock Island, about 5 miles from downtown Key West, which gives you the marina and a more laid-back base. Our complimentary shuttle runs into Old Town for the holiday events, shopping, dining and attractions.
Does The Perry offer special dining for Christmas Eve and Christmas Day?
Yes. Matt’s Stock Island Kitchen & Bar serves a three-course prix fixe dinner on December 24 and 25, 2026, from 5:30 to 9 PM. It’s $99 per person. Reserve through stayeos.com/mattsopentable or call 786.862.6621.
Are there any holiday events at the hotel?
Yes. We host the Holiday Lighted Boat Parade on Sunday, December 13, 2026, from 3 to 8 PM. It’s free and open to the public.
Are the pools open during the Christmas holiday?
Yes. Both waterfront pools are open, with poolside food and drinks and cabana rentals.
Is The Perry family-friendly?
Yes. We have double queen rooms, suites with room to spread out, two waterfront pools, dining on site and family-friendly excursions through the concierge.
Is The Perry pet-friendly?
Yes, we’re dog-friendly. Our dog-friendly hotel page has the details on fees and limits.
What activities are available in Key West during Christmas?
The concierge can book fishing charters, sunset cruises, sandbar excursions and sightseeing, subject to holiday availability.
Is parking available at The Perry?
Yes. On-site self-parking is $29 per night plus tax, and you’ll need a parking pass.
Book Your Key West Christmas Stay
Call 877.496.8712 or book direct for the Insider Offer.