PHOTO: Seafarer Resort and Beach

The Best Old School Florida Keys Hideaways

Jill Martin | January 30, 2018

Ah, the good ol’ days. Taking road trips with your parents to the Keys, staying in mom-and-pop motels along the shore, playing outdoors all day, and wishing on shooting stars each night. That is Old Florida and those mom-and-pop motels are about as Old School as you can get.

Sure, you can stay in big brand hotels with shiny new everything, but where’s the adventure in that? Instead, relive your childhood memories at one of these older, beloved resorts. Just remember, with age comes wear, so there’s no need to complain about the fabrics or noisy wall AC units. Instead, go outside and soak in those million dollar views. You’ll be wealthier for the experience. These are the best hideaways in the Florida Keys.

#10

Key West Marriott Beachside Hotel

Why it made the list

Just pulling into the parking lot will make you giddy, especially if you're a fan of retro, mid-century architecture. From the outside, this vintage motel is Old Florida all the way, and they just happen to have a prime location on the Atlantic. It was built in the late 1950s, survived Hurricane Donna in '61 (sort of), and its 18 rooms are still outdated by modern standards, although WiFi and an Ethernet port are now available in every room.

A whopping seven acres on the Gulf of Mexico, this is the pl Read More

#9

Little Conch Key

Why it made the list

Old school meets private island at Little Conch Key. Turn off the main highway and follow the path across the bridge to a secluded hideaway complete with conch cottages, some still boasting Dade County Pine walls and original tongue and groove floors. Gather with other guests at breakfast and their private beach.

Dare to venture off the main road and be rewarded with a sta Read More

#8

Seashell Beach Resort

Why it made the list

Old Florida charm is what you’ll find at this small 10-room motel on the Atlantic. Nothing fancy, nothing outstanding (except the view), just a simple room on the water where everyone gets to know each other as they vie for the oceanfront hammock, or squeeze past each other at the undersized pool.

It’s got the word "resort" in the name, but really, this is Read More

#7

Gulf View Waterfront Resort

Why it made the list

Bring your family and your pet to this true mom-and-pop property on the bayside of Grassy Key. Originally built in 1966, it’s got great bones, comfortable rooms, and a menagerie of creatures like Ziggy the tortoise and Mango the macaw. If you love simpler times, you’ll love spending time at the Gulf View.

This family run resort caters to its guests and their pets. Read More

#6

Sea Dell Motel

Why it made the list

Built in 1953, this roadside motel has a prime spot on Overseas Highway in the center of Marathon, and is only a few minutes from the best beach in the Keys--Bahia Honda. While its thick concrete exterior hasn’t changed, the interiors have been spruced up with paint and humble furnishings, but it definitely still qualifies for Old School status. Look for the burnt orange buildings.

It’s not on the water and it doesn’t offer a view, but the l Read More

#5

Ragged Edge Resort

Why it made the list

Without the big billboard on Overseas Highway that reads “RAGGED EDGE” and a handy arrow pointing the way, you might not ever find this rustic, oceanfront getaway tucked in a residential neighborhood. Bring your boat or fish from their dock, and enjoy bug-free Atlantic views from your screened patio. Make yourself at home in these simple, lived-in units.

It’s BYOB (bring your own boat) at this peaceful resort perc Read More

#4

Seafarer Resort and Beach

Why it made the list

An old fisherman in his bright yellow rain gear marks the spot of these cottages on the bay in Key Largo. And he’s not the only thing that’s old-timey around here: the paneling, bathroom tiles, bed spreads, jalousie windows… but somehow it all comes together in an almost charming sort of way. It’s all about the beach here, relaxing, and grilling out.

It may not be fancy, but all your basic needs will be met an Read More

#3

Popp's Motel

Why it made the list

Their last name has been on the sign since 1951, and now, four generations later, the Popp family is still creating magic for their guests, who are lucky enough to get one of their nine units on the bay. Surround yourself with coconut palms, original Dade County Pine paneling, tile from the 1950s, and good old-fashioned hospitality.

Popp’s is a quiet little place perfect for escaping the mode Read More

#2

Rainbow Bend

Why it made the list

The first thing you’ll notice is the classic sign (circa 1960), then the pastel pink exterior. And although the rooms are dated, and the WiFi is basically non-existent, there are a few pretty spectacular perks, like their freakishly good, white-linen restaurant that earns nearly five stars from every review site. You also get a free half-day boat rental for each day of your stay.

With complimentary use of a motorized skiff, a hot sit-down Read More

#1

Sugarloaf Lodge

Why it made the list

If the Brady Bunch had taken a family vacation to the Keys, this would have been the setting. The décor is fabulously vintage and just outside your door, you can enjoy all that the Keys has to offer with an onsite marina (think all kinds of watersport rentals) and a groovy Tiki Bar. So, put on your mood ring and pack your pet rock--this place is a trip, in the best way possible.

Family owned and operated since 1973, this is just the kind Read More

  • 10. Key West Marriott Beachside Hotel
    3841 N. Roosevelt Blvd., Key West,Florida,USA,33040
  • 9. Little Conch Key
    MM 62.3 OS, 62250 Overseas Hwy.,Conch Key,Florida,USA,33050
  • 8. Seashell Beach Resort
    57612 Overseas Highway,Marathon,Fl,33050
  • 7. Gulf View Waterfront Resort
    MM 58.7 BS, 58743 Overseas Hwy.,Grassy Key,Florida,USA,33050
  • 6. Sea Dell Motel
    5000 Overseas Highway,Marathon,Fl,USA,33050
  • 5. Ragged Edge Resort
    MM 86.5 OS, 243 Treasure Harbor Rd.,Islamorada, Florida,USA,33036
  • 4. Seafarer Resort and Beach
    MM 97.6 BS, 97684 Overseas Hwy.,Key Largo,Florida,USA,33037
  • 3. Popp's Motel
    95500 Overseas Hwy.,Key Largo,Florida,USA,FL 33037
  • 2. Rainbow Bend
    57784 Overseas Highway,Marathon,Florida,USA,33050
  • 1. Sugarloaf Lodge
    17001 Overseas Hwy.,Sugarloaf Key,Florida,USA,33042

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