Historic Hotels & Resorts in Sugarloaf Key

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Check availability on Sugarloaf Key Historic Hotels

Best Sugarloaf Key Historic Hotels

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
On the beach, beach towels

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (236)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is AU$1,266
includes taxes & fees
14 Aug - 15 Aug
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (119)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
The price is AU$491
includes taxes & fees
18 Aug - 19 Aug
Charming cottages, dockage, pool, just minutes to Key West
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Property grounds

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.8 out of 10, Exceptional, (112)
"Very comfortable house in a great location. "
The price is AU$823
includes taxes & fees
14 Aug - 15 Aug
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Exterior detail

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

10.0 out of 10, Exceptional, (117)
"My husband totally enjoyed our stay. Our accommodations were comfortable and kept us cool in the heat of the day. The kitchen is well appointed and the bicycles were the cherry on top. It is the BEST way to get around town, and the studio is centrally located. The courtyard provides privacy and a tranquil place to have a cup of coffee."
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Spec @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
Terrace/patio

Spec @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio

9.0 out of 10, Wonderful, (170)
"This was a great location and easy place to stay. We were able to walk to many locations in Old Town. The new updates are a nice addition to this location. Fresh paint, refrigerator, A/C and the patio is a great place to relax. "
The price is AU$479
includes taxes & fees
12 Sept - 13 Sept
Spec @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Pool

JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL

10.0 out of 10, Exceptional, (109)
"Great place to stay for our spring trip as a family of 3. "
The price is AU$1,856
includes taxes & fees
20 Aug - 21 Aug
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Beach nearby

CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (154)
"Great place"
The price is AU$380
includes taxes & fees
17 Aug - 18 Aug
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Beach nearby

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (121)
"Excellent location, walkable to Duval Street. We were able to park on-site and walk to everything. We would definitely stay here again."
The price is AU$378
includes taxes & fees
17 Aug - 18 Aug
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
FONTANA ~ Adults Only, Pool Access King Room at Azul Mansion!
Beach nearby

FONTANA ~ Adults Only, Pool Access King Room at Azul Mansion!

9.4 out of 10, Exceptional, (131)
"Over perfect. A couple blocks from good eats and beaches. Couldn’t have been more pleased"
The price is AU$373
includes taxes & fees
20 Aug - 21 Aug
FONTANA ~ Adults Only, Pool Access King Room at Azul Mansion!
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
Beach nearby

ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

9.6 out of 10, Exceptional, (130)
"This was a clean property which had everything including an ice machine and filttered water machine! Friendly professional people who work there and have thought of every extra touch to make your stay worry free! Great pool,and I stayed at the top "treehouse" room which had 2 sets of stairs to get to it. It was a large room and I enjoyed it with my own private deck!"
The price is AU$385
includes taxes & fees
14 Aug - 15 Aug
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
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.

Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Best resort!! My boyfriend just said “ I would say there 100 more times”. The staff was great, upgraded our rooms since it was a big family trip. Walkable distance to everything. Special shoutout the the restaurant chef on the property who cooked us the most unforgettable meal after we brought her a bunch of fresh fish from a fishing trip during the day!! "
ilma 4-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses

Frequently asked questions

What should a history enthusiast expect from a trip to Sugarloaf Key?
You're likely already making plans to see the places with historical relevance while on holiday in Sugarloaf Key. Why not absorb the local colour with a visit to the bars?
What's the best accommodation in Sugarloaf Key to learn about local history?
Based on our travel expertise, Sugar Loaf Lodge is a top hotel for history seekers booking on Expedia, and it features a marina and a restaurant.
How many historical hotels will I find in Sugarloaf Key?
Sugarloaf Key is home to 57 lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the most important historical places and other sights in Sugarloaf Key?
Favourite places to visit include Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Key. Additionally, you'll find Duval Street in the area.
What is a historic hotel like in Sugarloaf Key?
By choosing a historic hotel, you can stay in a building that has an officially recognised national historic designation. A palace, castle, grand home or even an old police station, pub, lodge or skyscraper can be identified as a historic hotel provided that it's a place of special interest. Traditional architecture and period features are often preserved in the public spaces and guestrooms of such hotels in Sugarloaf Key, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, while "historic hotel" is a term often used in the U.S. overall though the terms are similar. The building and architecture of historic hotels are generally what's most important. For a heritage hotel, mainly, it's cultural value along with how it influenced the community.
Do historic hotels in Sugarloaf Key have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, but every effort is made to preserve historic facades and treasured traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the usual amenities found at a contemporary hotel should be available at a historic hotel. Rest assured that when you choose a historic hotel in Sugarloaf Key, you won't find yourself staying at a place that's uncomfortable or rundown.