Public standard · claims are the managers' own

The Keys, By Mile Marker

Homes along the Overseas Highway whose own listing states the mile marker they sit at, Key Largo to Key West.

StayClubs, for now

Owner of last resort

The standard is the Keys' own address system: US 1 mile markers, MM 110 at Key Largo down to MM 0 at Key West. The test is only whether the manager's listing states the number. StayClubs holds the club until a Keys body takes it.

Nobody in the Florida Keys gives directions by street. The Overseas Highway runs 110 miles from Key Largo to Key West and every address is a green mile marker post, so managers write the MM number straight into their listings: Bay Therapy at MM 103, Sea Ranch at mile marker 83, Paradise at MM50. This club collects homes whose listing says where on the road they are, ordered north to south, so you can pick a stretch of the Keys before you pick a house.

Twelve homes from six managers, in five stretches of the highway from Key Largo to Key West. Each links to the manager; you book with them.

Browse here12 homes, 6 management companies, one reason to be on the same page.

Book with the managerEvery link goes to the company's own booking site. Prices, photos, and availability live there.

Or send your dates"Check dates" forwards your dates and party size to the manager and opens their page.

The homes

What qualifies, exactlyThe manager's own listing page states the home's Overseas Highway mile marker (for example MILE MARKER: 103, located at mile marker 83, Approx. MM51, above the Mile 0 location). The number is quoted in each claim. Listings that only say Islamorada or Marathon with no MM do not qualify. There is no outside authority; the mile marker system itself is maintained by the Florida Department of Transportation on US 1. Key West proper is thin because its managers give street addresses, not markers.

Key Largo (MM 110 to 90)

Event site

The top of the Keys, John Pennekamp Coral Reef State Park country.

Keys Holiday Rentals

Preview from Keys Holiday Rentals's listing

Bay Therapy

Key Largo, FL · Keys Holiday Rentals

Sleeps 83 BR

Listing: bayside canal home almost directly across the Overseas Highway from John Pennekamp; 28-day minimum, whole months only.

Listing states: “Listing header reads MILE MARKER: 103 (bayside canal home, Key Largo).” Source, as displayed on the listing, September 2026.

See the home

Found on Keys Holiday Rentals's site. Facts per the listing, September 2026.

Freewheeler Vacations

Preview from Freewheeler Vacations's listing

51 Jewfish Avenue

Key Largo, FL · Freewheeler Vacations

Sleeps 63 BR

Listing: ground-level three-bedroom home, new to the rental market.

Listing states: “Located in the highly desirable Jewfish neighborhood at Mile Marker 103.5” Source, as displayed on the listing, September 2026.

See the home

Found on Freewheeler Vacations's site. Facts per the listing, September 2026.

Islamorada (MM 90 to 72)

Event site

Plantation Key through Lower Matecumbe; the Village of Islands.

Florida Keys Vacation Rentals (Schmitt)

Preview from Florida Keys Vacation Rentals (Schmitt)'s listing

Lobster Shores

Islamorada, FL · Florida Keys Vacation Rentals (Schmitt)

Sleeps 63 BR

Listing: two bedrooms up with a screened balcony over the canal, a third bedroom down; boating access to Bay or Atlantic.

Listing states: “located in sought-out neighborhood Venetian Shores located at mile marker 86 Bayside” Source, as displayed on the listing, September 2026.

See the home

Found on Florida Keys Vacation Rentals (Schmitt)'s site. Facts per the listing, September 2026.

Freewheeler Vacations

Preview from Freewheeler Vacations's listing

Sea Ranch

Islamorada, FL · Freewheeler Vacations

Sleeps 84 BR

Listing: two private cottages on the Atlantic with a private sandy beach, pier and beachside pool.

Listing states: “Located in the heart of Islamorada at mile marker 83” Source, as displayed on the listing, September 2026.

See the home

Found on Freewheeler Vacations's site. Facts per the listing, September 2026.

Keys Holiday Rentals

Preview from Keys Holiday Rentals's listing

Villa Riolo

Islamorada, FL · Keys Holiday Rentals

Sleeps 62 BR

Listing: an updated stilt home offered by its owners for the first time; 28-day minimum.

Listing states: “Listing header reads MILE MARKER: 76.5 (gated oceanside house on a canal).” Source, as displayed on the listing, September 2026.

See the home

Found on Keys Holiday Rentals's site. Facts per the listing, September 2026.

Marathon and the Middle Keys (MM 65 to 47)

Event site

Grassy Key, Key Colony Beach and Marathon, down to the Seven Mile Bridge.

Florida Keys Vacation Rentals (Schmitt)

Preview from Florida Keys Vacation Rentals (Schmitt)'s listing

SeaSpell Pool Home

Grassy Key, FL · Florida Keys Vacation Rentals (Schmitt)

Sleeps 104 BR

Listing: a gated Gulf-front estate with over 200 feet of seawall and the pool set for the sunsets; license VACA-22-308 shown.

Listing states: “Location: Middle Keys, Grassy Key, Approx. MM58, 4 Bedroom, 4 Bath Single Family Pool Home with Hot tub, Gulf Front” Source, as displayed on the listing, September 2026.

See the home

Found on Florida Keys Vacation Rentals (Schmitt)'s site. Facts per the listing, September 2026.

Florida Keys Vacation Rentals (Schmitt)

Preview from Florida Keys Vacation Rentals (Schmitt)'s listing

Sombrero Pool Home

Marathon, FL · Florida Keys Vacation Rentals (Schmitt)

Sleeps 83 BR

Listing: pool, spa, dockage and a half mile from Sombrero Beach; license VACA-20-1371 shown.

Listing states: “Location: Middle keys, Approx. MM51, Sombrero Beach area” Source, as displayed on the listing, September 2026.

See the home

Found on Florida Keys Vacation Rentals (Schmitt)'s site. Facts per the listing, September 2026.

Florida Keys Vacation Rentals (Schmitt)

Preview from Florida Keys Vacation Rentals (Schmitt)'s listing

Paradise at MM50

Marathon, FL · Florida Keys Vacation Rentals (Schmitt)

Sleeps 83 BR

Listing: across from the golf course in Sombrero, 50 feet of dockage with a fish cleaning table and bait freezer.

Listing states: “The listing's own name states the marker: Paradise at MM50.” Source, as displayed on the listing, September 2026.

See the home

Found on Florida Keys Vacation Rentals (Schmitt)'s site. Facts per the listing, September 2026.

The Lower Keys (MM 40 to 5)

Event site

Big Pine, the Torch Keys, Summerland, Cudjoe and Sugarloaf.

Action Keys Realty

Preview from Action Keys Realty's listing

Blue Marlin

Little Torch Key, FL · Action Keys Realty

Sleeps 63 BR

Listing: a three-bedroom home down a private lane overlooking Pine Channel, gulf side.

Listing states: “Large boat basin accommodates most all boats with direct access to Pine Channel at mile marker 30” Source, as displayed on the listing, September 2026.

See the home

Found on Action Keys Realty's site. Facts per the listing, September 2026.

Action Keys Realty

Preview from Action Keys Realty's listing

Casa Caribe

Summerland Key, FL · Action Keys Realty

Sleeps 42 BR

Listing: across from Summerland Marina with a 60-foot dock, quick boating to Looe Key.

Listing states: “Listing's features list includes Mile Marker 25.” Source, as displayed on the listing, September 2026.

See the home

Found on Action Keys Realty's site. Facts per the listing, September 2026.

Last Key Realty

Carefree on Cudjoe

Cudjoe Key, FL · Last Key Realty

Sleeps 93 BR

Listing: private pool, over 100 feet of dockage and a 14,000-pound boat lift; 29-night minimum.

Listing states: “CAREFREE ON CUDJOE is located at Mile Marker 23 on Cudjoe Key” Source, as displayed on the listing, September 2026.

See the home

Found on Last Key Realty's site. Facts per the listing, September 2026.

Key West (MM 4 to 0)

Event site

The end of the road.

Vacation Homes of Key West

Preview from Vacation Homes of Key West's listing

Key West Mile Zero Suite

Key West, FL · Vacation Homes of Key West

Sleeps 42 BR

Listing: a second-floor suite in a Victorian building with a view of the Mile 0 sign below.

Listing states: “now you can luxuriously live right next to this landmark, perched above the Mile 0 location (505 A Whitehead St.)” Source, as displayed on the listing, September 2026.

See the home

Found on Vacation Homes of Key West's site. Facts per the listing, September 2026.

Found and not used

Managers that state mile markers only on hub pages, managers whose listing pages would not render, Keys managers with no mile marker in any listing, and the license numbers that point to a possible second club.

Keys Caribbean Vacation Rentals. Its hub page states MM per community (Mariner's Club MM 97.5, Angler's Reef MM 84, Hawks Cay MM 61, Coral Lagoon MM 53), but the unit pages are a booking engine that renders nothing without a browser., Key Largo to Marathon: source, September 2026
Seven Keys Vacations (213 listing pages read, none states a marker). Rent Key West Vacations (228 pages, none). Last Key Realty's Old Town homes (155 pages, none; its Lower Keys homes do: Baypoint Oasis MM 15, Blue Horizon MM 17, Infinite Horizons MM 10, two homes at Mile Marker 5 in Key Haven)., Key West: source, September 2026
Further qualifying homes held for count: Keys Holiday Rentals (Twice the Charm MM 98.5, Moon Bay MM 104.3, Sandglass MM 74.9, Sunshine Place MM 84.3, Casa de Sunshine MM 69); Freewheeler (LeSerra Lane MM 76.5, Paradise Point MM 76, Bay Harbour MM 74.5, Futura Yacht Club MM 88.5); Schmitt (Views of 7-Mile Bridge MM48, Gulf Breeze MM52.5, La Casa Habana MM 58, Ohana House MM17, Sea Escape MM 23)., Key Largo to Sugarloaf: source, September 2026
A possible second club: Schmitt listings print permit numbers (PLR2017-0048022, PLR2018-00587, which appear to be Monroe County vacation rental permits; VACA numbers from the City of Marathon; STR numbers from Key Colony Beach)., Marathon area: source, September 2026
Coco Plum (a 20-villa resort, no per-home page). Florida Keys Rental Store (Guesty pages render only with JavaScript). keysvacationrentals.com (parked), americancaribbean.com (real estate sales), historickeywest.com (404)., various: source, September 2026