Historic Hotels & Resorts in Islamorada from NZ$352

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada Historic Hotels

Tonight
21 Feb - 22 Feb
Tomorrow
22 Feb - 23 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar

Our top choices for Islamorada historic hotels

Fridge, microwave, oven, stovetop

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (213 reviews)
"Absolutely wonderful property in every way!"
United States
Christopher K.
The price is NZ$1,026
includes taxes & fees
23 Mar - 24 Mar
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Indoor pool, outdoor pool

Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!
Rock Harbor
10.0 out of 10, Exceptional, (94 reviews)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
United States
Gene Z.
The price is NZ$1,549
includes taxes & fees
28 Feb - 1 Mar
Ohana Cay 2brm/2bth - Book your getaway!
On the beach, sun-loungers, beach towels

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (172 reviews)
"Loved this place and will stay again if we go back to the Keys. Gated community with golf cart to go to the pier with great community resources, grills and sitting areas. Favorite part was the lagoon in the middle of the community not far from the screened in back porch. Full of fish you can swim with and calm beach area that is clean and nice with shade when you need it. We didn’t want to leave this place. Highly recommend!!"
United States
Chandler G.
The price is NZ$2,321
includes taxes & fees
18 Mar - 19 Mar
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
On the beach, sun-loungers, beach towels

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (195 reviews)
"Very relaxing vacation "
United States
Teresa M.
The price is NZ$2,176
includes taxes & fees
16 Mar - 17 Mar
NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Outdoor pool, a heated pool

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Rock Harbor
9.8 out of 10, Exceptional, (106 reviews)
"Loved the location, the decor and the pool area!"
United States
Laureen h.
The price is NZ$2,584
includes taxes & fees
28 Feb - 1 Mar
NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Top Islamorada Hotel Reviews

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Great staff. Coffee machine in room was defective. Curtains dirty and faulty closing. Everything else clean and convenient."
Ronald 5-night trip
Posted 2 days ago
La Siesta Resort & Villas
Islander Resort

Islander Resort

10/10 Excellent
"We had an incredible time at the Islander! We were expecting a regular big hotel on the beach kind of stay, but The Islander offers bungalow-style accommodations with private lanai/patios for every room! It made the place feel so much more chill. The grounds were beautiful with abundant landscaping, palm trees, and tons of seating options to lounge on and off the beach. "
Julia 3-night trip
Posted 4 days ago
Islander Resort

Frequently asked questions

What should a history enthusiast expect from a trip to Islamorada?
You're already probably planning a visit to historically relevant sites while you're staying in Islamorada. And while you're here, you can check out the entertainment choices and scenic seaside. And also relish a stop at the seafood restaurants in this relaxing area.
How many historically relevant hotels are there in Islamorada?
Islamorada is home to 908 hotels bookable on Expedia though not many historic hotels to choose from.
What are the most important historical sites and other places to visit in Islamorada?
Favourite places to visit include Everglades National Park, Bud n' Mary's Dive Center and Islamorada County Park. A couple of additional sights to add to your itinerary are Anne's Beach and Fiesta Key.
What is a historic hotel like in Islamorada?
Guests who book a historic hotel can stay in a place that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often found in the guestrooms or communal spaces of such hotels in Islamorada, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. overall though the terms are similar. The architecture and building of a historic hotel tends to be what's most significant. For a heritage hotel, it's often the cultural value along with how it inspired the community.
Do historic hotels in Islamorada have modern facilities?
Hotel interiors feature the modern conveniences and safety features you might expect, but every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the popular amenities found at a contemporary hotel should be available at a historic hotel. When you choose a historic hotel in Islamorada, don't worry that you'll be staying at a place that's uncomfortable or rundown.

Explore a world of travel with Expedia