Key West Holiday Historic Inn Tours 2026

The Key West Holiday Historic Inn Tours run on two Friday nights in 2026: Dec. 11 and Dec. 18, 6 to 8 PM, with check-in at 5:30 PM. The dates come from the Holiday Fest calendar kept by Key West Inns and the Lodging Association of the Florida Keys and Key West, which posted them in September. Tickets go on sale Nov. 15. When we checked on Oct. 21, 2026, the organiser had not published which inns take part or what a ticket costs. Christmas in Key West is an independent planner published by LPE Realty LLC. We are not the City of Key West, Schooner Wharf, the Historic Seaport, the Lodging Association or any venue, and we sell no tickets.

• The Holiday Fest calendar lists "Holiday Historic Inn Tours" Night 1 on Dec. 11, 2026 and Night 2 on Dec. 18, 2026, 6:00 to 8:00 pm, each with "5:30pm check-in. Visit and tour beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings. Tickets available beginning Nov. 15." Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar

Who runs the inn tours

The tours belong to the Key West Holiday Fest, run by Key West Inns and the Lodging Association. keywestholidayfest.com carries the line “Purchase Your Holiday Historic Inn Tours Tickets Here!”, lists Key West Historic Inns as presenting sponsor, and gives a contact block for the Florida Keys Lodging Association, 818 White Street, Suite #8, (305) 296-4959. One caution: on Oct. 21, 2026 that site’s main heading still read “Key West Holiday Fest 2025”, while its calendar records were dated 2026.

• keywestholidayfest.com says "Purchase Your Holiday Historic Inn Tours Tickets Here!" and lists "Key West Historic Inns" as presenting sponsor. Its contact block reads "Florida Keys Lodging Association", "818 White Street, Suite #8", "(305) 296-4959". On 2026-10-21 its main heading still read "Key West Holiday Fest 2025". Key West Holiday Fest (Key West Inns)
• Holiday Fest calendar: "Key West Holiday Fest, the southernmost city's annual joyous celebration of the season, kicked off on Thanksgiving Eve and continues through December." It quotes Jodi Weinhofer, President of the Lodging Association of the Florida Keys and Key West. Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar

• The brief called it the "Old Island Restoration Foundation Holiday Historic Inn Tour". OIRF's own site lists only its Key West Home Tours (private homes plus the Oldest House, Dec. 29-30, 2026). The Holiday Historic Inn Tours are listed by Key West Inns / the Lodging Association (keywestholidayfest.com). They are two different events. Old Island Restoration Foundation; Key West Holiday Fest (Key West Inns)

What the evening is

The organiser’s description: “Visit and tour beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings.” Each night is two hours, from 6 to 8 PM, after a 5:30 PM check-in. The calendar listing does not say where check-in happens.

Not posted yet (Oct. 21, 2026)

• The list of participating inns for 2026.
• The ticket price for 2026.
• A 2026 ticket page. Tickets are listed as “available beginning Nov. 15”.

We will not guess any of these from earlier years. Our date checker carries both nights now and will carry the details when the Lodging Association posts them.

The other tour: OIRF Key West Home Tours, Dec. 29 and 30

The Old Island Restoration Foundation says its 67th Key West Home Tours are a four-month series giving access to privately owned historic homes. The December dates are Tuesday, Dec. 29 and Wednesday, Dec. 30, 2026, with homes open 1 to 4 PM each day. Later dates are Jan. 22-23, Feb. 12-13 and March 12-13, 2027. Every ticket covers that month’s four featured private homes plus the Oldest House.

• Old Island Restoration Foundation: "Our 67th Annual Key West Home Tours is a four-month series offering access to privately owned historic Key West homes." Dates: "December 29-30, 2026 (Tuesday & Wednesday)", then Jan. 22-23, Feb. 12-13 and March 12-13, 2027. "Homes are open from 1:00pm until 4:00pm each day". "Every ticket includes access to that month's four featured private homes and the Oldest House." Old Island Restoration Foundation: Key West Home Tours Info & FAQ

Prices and rules (OIRF)

• $55 per person, or $45 for museum members; $180 for a package of all four months.
• All ticket sales are final and non-refundable.
• House addresses go on the OIRF website one week before your tour.
• No transportation is provided, and there is no designated parking for personal vehicles.
• Children may come but must stay with an adult at all times.
• Homes are not always ADA compliant.

• OIRF: "$45 per individual for museum member", "$55 per individual for non-museum member", "$180 package for all four months". "All ticket sales are final and non-refundable." Old Island Restoration Foundation: Key West Home Tours Info & FAQ
• OIRF: "House addresses will be on our website one week prior to your tour." "There is no formal transportation provided." "There will be no designated parking for personal vehicles". "Children are allowed on the tour but must be accompanied by an adult at all times." "Note: homes are not always ADA compliant". Old Island Restoration Foundation: Key West Home Tours Info & FAQ

Side by side

	Holiday Historic Inn Tours	OIRF Key West Home Tours
Run by	Key West Inns / Lodging Association	Old Island Restoration Foundation
2026 dates	Fri. Dec. 11 and Fri. Dec. 18	Tue. Dec. 29 and Wed. Dec. 30
Hours	6 to 8 PM, check-in 5:30 PM	1 to 4 PM
What you see	Decorated historic inns, with treats and samplings	Four private historic homes plus the Oldest House
Price	Not posted for 2026	$55; $45 members; $180 all four months
Tickets	From Nov. 15 (keywestholidayfest.com)	OIRF, non-refundable

The Oldest House Museum, free

OIRF’s Plan Your Visit page lists the Oldest House Museum at 322 Duval Street as open daily with free general admission. It dates the house to circa 1829. You do not need a home-tour ticket to see it on other days.

• OIRF Plan Your Visit: "Open Daily", "322 Duval St.", "General Admission" "Free". "Built circa 1829, The Oldest House Museum offers a glimpse into the people, architecture, and stories that shaped early Key West." Old Island Restoration Foundation: Plan Your Visit

More historic interiors in December

• Truman Little White House: holiday evening house tours with a presidential holiday card presentation, Dec. 22 and 23, 2026. Details and prices are on our holiday lights tours page.
• Custom House: the Holiday Concert and Bazaar is on Friday, Dec. 11, 5 to 8 PM, the same night as inn tour Night 1. The bazaar opens at 5 PM and inn check-in is at 5:30 PM, so plan which one comes before the other.
• Hemingway Home and Museum: open daily, 9 AM to 5 PM for walk-ins, $19 adult general admission, according to the museum.
• Audubon House and Tropical Gardens, 205 Whitehead Street: 9:30 AM to 4:15 PM daily.

• The City of Key West calendar lists "2026 Custom House Holiday Concert & Bazaar – City Property Event Notice" on "Friday, December 11, 2026", "5:00 PM – 8:00 PM": "The event takes place at the Custom House and Clinton Place. Front Street will be closed in front of the Custom House from Greene Street to Whitehead Street." KWAHS says students' trees will be displayed "in the week leading up to our Annual Holiday Concert & Bazaar on December 11th." City of Key West: Calendar event notice; Key West Art & Historical Society: Holiday Concert & Bazaar
• Hemingway Home and Museum: "Museum is open daily, 365 days a year", "9:00am-5:00pm for walk-in visits", "Tours start every 15 minutes with the first tour starting at 9:15am". Adult "General Admission – $19"; "Children 5 and younger are FREE". Ernest Hemingway Home and Museum: Rates & Info
• Audubon House & Tropical Gardens lists "Admissions & Hours" Monday through Sunday "9:30am" to "4:15pm", "Gallery & Gift Shop" to "5:00pm", at "205 Whitehead Street". No Christmas Day hours are posted. Audubon House & Tropical Gardens

Getting between houses

Neither tour provides transport, and OIRF says there is no designated parking. Plan on walking in Old Town. The City’s Key West Rides on-demand buses run 6 AM to 8 PM, which covers the home tours but not the end of an inn-tour night. Lots and the Old Town garage are on our parking page. If the old houses are the reason you keep coming back, our living in Key West page has City and Census facts about the island.

• City of Key West: "Key West Rides On-Demand is an innovative form of transportation that will replace the North and South Lines". "This is a bus stop-to-bus stop service". Hours "Monday" to "Sunday 6 AM" to "8 PM", "(No service on Thanksgiving Day, Christmas Day, and New Year's Day)." Booking help: "305-809-3910". City of Key West: Key West Rides On-Demand Bus Service

The rest of December, from the Harbor Walk of Lights to the boat parade the night after Night 1, is on our holiday events page.

Questions people ask

Dates, rules and hours can change. The organisers have the final word: City of Key West: Visitors