A beach with white lounge chairs, a covered pavilion, and palm trees.

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Check availability on Islamorada Historic Hotels

Our top choices for Islamorada historic hotels

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

1. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is ￥102,689
￥127,080 total
includes taxes & fees
Nov 18 - Nov 19
The Islands of Islamorada
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,811 reviews)
"Location is amazing make sure to book a balcony with a view"
United States
Olga Vasiliy
The price is ￥24,405
￥36,370 total
includes taxes & fees
Nov 19 - Nov 20
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,162 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is ￥28,400
￥43,538 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

4. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is ￥21,078
￥28,170 total
includes taxes & fees
Nov 18 - Nov 19
La Jolla Resort
A boat docked near a waterfront with a hammock and a chair, surrounded by greenery and palm trees.

5. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (467 reviews)
"Very helpful staff and great location"
United States
David
The price is ￥29,011
￥34,415 total
includes taxes & fees
Dec 7 - Dec 8
Casa Morada
A bathroom with a large bathtub, a view of the sea, and a pier with boats.

6. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,514 reviews)
"Clean room, friendly staff and food was good."
United States
Nicholas
The price is ￥28,648
￥43,784 total
includes taxes & fees
Nov 17 - Nov 18
Cheeca Lodge & Spa
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

7. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is ￥43,000
￥59,963 total
includes taxes & fees
Nov 15 - Nov 16
Bayside Villas by Islander Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

8. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (311 reviews)
"Great place to stay!"
United States
Liosbel
The price is ￥32,740
￥48,387 total
includes taxes & fees
Nov 29 - Nov 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, a lamp, and a large window with a view.

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,003 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
The price is ￥21,252
￥29,081 total
includes taxes & fees
Nov 29 - Nov 30
Hadley Resort and Marina
A beachside resort with a covered seating area, a wooden deck, and a view of the ocean.

10. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (279 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
The price is ￥21,984
￥24,732 total
includes taxes & fees
Nov 12 - Nov 13
Ragged Edge Resort & Marina
A wooden deck with white railings, outdoor seating, and a view of the sea with palm trees.

11. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.6 out of 10, Exceptional, (561 reviews)
"Beautiful place hidden in Tavenier Great staff and the best sunset in the keys"
United States
ED
The price is ￥43,942
￥55,657 total
includes taxes & fees
Nov 18 - Nov 19
Coconut Palm Inn
Terrace/patio

12. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,587 reviews)
"We stayed for 4 nights, place was great. Clean and relaxing."
United States
John
The price is ￥19,629
￥29,214 total
includes taxes & fees
Nov 18 - Nov 19
Lime Tree Bay Resort
A beach with lounge chairs, palm trees, and a view of the water.

13. Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (836 reviews)
"Excellent Stay!"
United States
Annette
The price is ￥23,621
￥30,139 total
includes taxes & fees
Dec 9 - Dec 10
Atlantic Bay Resort
A covered outdoor area with a view of a beach and palm trees.

14. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,207 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is ￥14,311
￥16,100 total
includes taxes & fees
Nov 17 - Nov 18
Rock Reef Resort
A wooden bridge leading to a beach area with palm trees and a yellow kayak.

15. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (268 reviews)
"This may be my favorite place I've stayed in the Keys! So quaint and the location and breakfast were amazing. We kayaked to the mangroves, ate at the wonderful restaurant across the street (Ballyhoos), and thoroughly enjoyed the beach area"
United States
Brittany
The price is ￥15,596
￥19,767 total
includes taxes & fees
Nov 17 - Nov 18
Seafarer Key Largo
A balcony with a view of the sea, a beach, and a thatched hut.

16. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,003 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is ￥19,198
￥21,598 total
includes taxes & fees
Nov 11 - Nov 12
Sunset Cove Beach Resort
A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

17. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (34 reviews)
"Very friendly staff"
United States
Maria
The price is ￥29,437
￥33,117 total
includes taxes & fees
Nov 16 - Nov 17
The Ocean View Inn & Pub
A beach with a thatched-roof hut, lounge chairs, and a swimming area.

18. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,009 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
The price is ￥14,557
￥16,377 total
includes taxes & fees
Nov 29 - Nov 30
The Pelican Key Largo Cottages
A bedroom with a wooden bed, a nightstand, a lamp, and a view of the outdoors through large windows.

19. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,005 reviews)
"Excellent location"
United States
kelly
The price is ￥17,657
￥21,642 total
includes taxes & fees
Nov 11 - Nov 12
Drift Hotel
An aerial view of a resort with a large pool, palm trees, and a beach.

20. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,004 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is ￥41,680
￥55,627 total
includes taxes & fees
Nov 29 - Nov 30
Playa Largo Resort & Spa, Autograph Collection
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.
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Top Islamorada Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"We absolutely loved our stay at Islander! It was such a peaceful, relaxing resort, and we’re so glad we chose it for our honeymoon. The staff was incredibly helpful and welcoming, and the shuttle service was a wonderful perk for getting to and from nearby restaurants. We also really enjoyed the resort’s amenities, especially kayaking, fishing, and bike riding. Everything from check-in to check-out was easy and seamless, making our stay that much more enjoyable. We would definitely stay at Islander again and highly recommend it to anyone looking for a relaxing getaway!"
Trevor 4-night trip
Posted 4 days ago
Islander Resort

Frequently asked questions

What should a history enthusiast expect from a trip to Islamorada?
You're likely already making plans to see the sights of historical relevance during your vacation 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 will I find in Islamorada?
In Islamorada, you'll find 850 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.
What are the must-see historical sites and other places to visit in Islamorada?
Favorite places to visit include Bud n' Mary's Dive Center, Robbie's of Islamorada, and Anne's Beach. A couple of additional sights to add to your agenda are Fiesta Key and Everglades National Park.
What is a historic hotel like in Islamorada?
Guests who book a historic hotel can enjoy a vacation in a place that has an official historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically preserved within the guestrooms or public spaces of historic hotels in Islamorada, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of a historic hotel tends to be the most significant aspect. For a heritage hotel, it's often the cultural value as well as how it influenced the community.
Do historic hotels in Islamorada have modern facilities?
Hotels have the safety features and modern conveniences you expect to find, while every effort is made to preserve treasured traditions and historic facades. WiFi, heating and air conditioning, updated bathroom facilities, and the usual amenities found in most hotels will be available in a historic hotel. Rest assured that when you choose a historic hotel in Islamorada, you won't find yourself staying at a place that is rundown or uncomfortable.

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