top of page

Take a Romantic Retreat at These Historic Hotels in Florida

Updated: 1 day ago

From the turn of the century gilded age to the art deco jazz age, these opulent and stunning historic hotels in Florida are still in operation today. Whether for an over the top wedding (can I come?), a walk-through or a meal on a Sunday drive, or for a romantic overnight stay, this wonderful array of accommodations all offer stories to tell. Many of these can be found on the register of Historic Hotels of America, a National Trust for Historic Preservation.


Note: Always Pack Tissues represents many tried and tested travel sites as what is called an 'affiliate' partner. That means if you click on my ads I may get a commission from a resulting sale.


Historic Hotels in North Florida


The Lodge at Wakulla Springs

550 Wakulla Park Dr., Crawfordville, Florida 32327


This understated hotel in Florida's Panhandle near Tallahassee showcases a time when investors saw beyond mud and swamp lands, creating attractions and opulent lodging for visitors. The Florida "land boom" was responsible for many of the historic parks and hotels in Florida today.

alligator swims in a spring

Opened: 1937

Visit For: the affordable dining room serving up Southern dishes, take the jungle cruise river boat tour along Wakulla Springs, visit the soda fountain for an ice cream, or enjoy serene nature which inspired several Hollywood films onsite

More information and booking: The Lodge at Wakulla Springs



Casa Monica Resort & Spa

95 Cordova Street, St. Augustine, FL 32084


This ornate historic hotel in St. Augustine is full of charm reminiscent of nights in Casablanca, or perhaps Spanish Granada. The blend of Moroccan moods and Mediterranean luxuries serves up a classic dish of extravagance in this centralized hotel to all the Old Town sites.


Opened: 1888

Visit For: regal interiors and convenience to all of St. Augustine's offerings

More information and booking: Casa Monica Resort



Casa Marina

691 1st St N, Jacksonville Beach, FL 32250


This affordable beachfront hotel plays host to countless weddings and events, and once hosted infamous names in history like Rockefeller, Chaplin, Al Capone, FDR and Truman, to name just a few. It even acted as military housing in WWII.


Opened: 1925

Visit For: ocean views from the rooftop bar and specialty brunches

More information and booking: Casa Marina Hotel




Historic Hotels in Central Florida


Historic Lakeside Inn

100 North Alexander St., Mount Dora, FL


Boasting the title of the oldest continuously operating hotel in all of Florida, the historic Lakeside Inn is a quaint and charming option for traveler's looking for a bit of peace and quiet in adorable Mt. Dora. Less than 45 minutes from Orlando, Mt. Dora has lovely lanes full of boutiques and restaurants worthy of their annual events like their impressive Christmas lights or their colorful art festival.


Opened: 1883

Visit For: Sunday lunch in the restaurant, walks to the lake (where you can catch a boat tour) or take in happy hour at their nostalgic lounge

More information and booking: Lakeside Inn at Lake Dora



Don Cesar

3400 Gulf Boulevard,St. Pete Beach, Florida 33706


The timeless grandeur of this bubble gum colored hotel dominates the skyline of St. Pete Beach. Its majestic towers and ornate interiors once offered rest for greats like F. Scott Fitzgerald and more.


skyline of st pete beach with a pink hotel in the background

Opened: 1928

Visit For: quiet beach retreats and swimming pools

More information and booking: Don Cesar Hotel



The Vinoy

501 5th Ave NE, St. Petersburg, FL 33701


The Vinoy's whimsical pink facade is adorned with modern interior trappings in the bedrooms, while the lobby, foyer and outdoor cocktail bar ooze with golden age charms. Grab a sunset drink on their terrace, spilling out into a breezy lounge area overlooking the St. Petersburg waterfront.


Opened: 1925

Visit For: strolls along the St. Petersburg waterfront and parks, or along the marina to see boats and pelicans, use their swimming pool before walking to town for a meal or visit the Dali Museum or Chihuly Collection nearby.

More information and booking: The Vinoy



Fenway Hotel

453 Edgewater Dr., Dunedin, FL 34698


Walking distance to the waterfront village of Dunedin, explore shops and restaurants in quiet surrounds. The Fenway Hotel offers creatively decorated rooms with music in mind, as the Dunedin hotel was in fact once the county's first radio station. Throughout the hotel find nods to the speakeasy era and plenty of spaces to enjoy a relaxing drink.


exterior of a century old hotel named fenway on the front

Opened: 1927

Visit For: music themed rooms, a quiet pool, and a lovely rooftop bar

More information and booking: The Fenway Hotel



The Hacienda

5621 Main St, New Port Richey, FL 34652


An affordable hotel situated along the riverwalk in New Port Richey, this attractive Spanish-inspired building became a hot spot for film stars and writers in the roaring '20s, earning the area the name "Hollywood East". Simply furnished and friendly, this is a very approachable hotel on the west coast of Central Florida.


Opened: 1927

Visit For: relaxed lodgings and an enjoyable dining room

More information and booking: The Hacienda



Historic Hotels in South Florida


The Savoy

425 Ocean Dr, 33139, Miami Beach, Florida


Tropical art deco vibes glitz and glitter in every corner of this beautifully decorated resort and beach club in Miami Beach. Visitors won't want to leave the paradise setting, but if they do, the arts and culture epicenter of Ocean Drive is steps away, along with the SoFi district's no frills dining scene. Feel comfortable and pampered in a setting fit for the Gatsby era.


miami beach with sand and palm trees, tall hotels

Opened: 1935

Visit For: the private beachfront and pool areas, lounges and bars

More information and booking: The Savoy



Casa Faena

3500 Collins Ave, Miami Beach, FL 33140


At Casa Faena, expect a beautiful and colorful boutique hotel steps from the action of Miami Beach. Blending Spanish and Mediterranean charms, this very affordable hotel is known for its festivities. Luxuriate in artful spaces and exceptional lounges at this great pick in Miami.


orange cushions on a bamboo outdoor couch set with palm trees in the background

Opened: 1928

Visit For: check out their lineup of entertainment and music at the Living Room lounge, Saxony Bar or Faena Theater, all on site.

More information and booking: Casa Faena



Colony Hotel & Cabana Club

525 E Atlantic Ave, Delray Beach, FL 33483


Classic and tropical trimmings adorn the Colony Hotel's interiors in historic downtown Delray Beach. Their Cabana Club, two miles away, offers hotel guests private beach access, cabanas, a pool and more. The hotel features the original staff elevator and switchboard in the lobby, among other antique artifacts.


Opened: 1926

Visit For: cool Florida nights outside at their bar, or strolling for a meal through the historic Atlantic Avenue. Spend the day at the beach club before retreating back to your comfortable historic room.

More information and booking: Colony Hotel & Cabana Club



The Breakers Palm Beach

One South County Road, Palm Beach, FL33480


Having met several fires in its young life along the sand of Palm Beach, the opulent Breakers hotel emerged more and more grand upon each rebuild. By 1926, its third iteration of architectural changes was carried out by the same teams who were busy founding the Waldorf Astoria in New York, among others. With Italian influences and droves of infamous historical figures coming to visit, the Astor's, the Carnegie's, the Vanderbilt's and the Rockefeller's were all patrons of this truly splendid hotel.


palm trees surround a colorful stone fountain with patio lighting

Opened: 1896

Visit For: grand salons, oceanfront pools, luxurious trappings and exquisite dining

More information and booking: The Breakers Hotel



The Biltmore Hotel Miami Coral Gables

1200 Anastasia Ave, Coral Gables, FL 33134


Like most on this list, the list of the rich and famous who stayed here is simply unmatched. In its opening years of the Jazz Age, the Biltmore held aquatic galas like synchronized swimming to draw crowds and entice visitors to see more than just their golf course, polo fields, tennis courts and country club. Resplendent with luxury, the graceful Biltmore hotel in its name alone is synonymous with opulence.


Opened: 1926

Visit For: many golf offerings, its spa, their wine dinner or perhaps an afternoon tea

More information and booking: The Biltmore Hotel Miami

21 views0 comments

Hi, I'm Maria!

Globetrotting since 1995, I'm not a blogging nomad or a social influencer.

I'm a traveler. I'm a storyteller.

And I'm here to inspire you to

Travel More.

 

Learn More About Me

 

Make Your Travel Dreams A Reality

Stop waiting for someday, and start traveling more TODAY. You're not too old, too poor, or too busy. You CAN travel more. Let me show you how.

Subscribe and Get a Free Itinerary Template

Thanks for submitting!

bottom of page