Find Historic Hotels in Tradewinds, FL

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Our top choices for Tradewinds historic hotels

Outdoor dining
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Matlacha
9.4 out of 10, Exceptional, (49)
"The atmosphere and art very local"
United States
Cindy
$170 nightly
The price is $187
Dec 12 - Dec 13
Total with taxes and fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
On the beach
Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7

Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7

Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7
3.0 star property
Captiva
8.0 out of 10, Very Good, (10)
"We loved being able to walk out to the beach without having to drive and the availability of beach chairs and umbrellas to carry with us. We also loved being able to walk to restaurants and the local grocery store nearby. Our room was pretty, comfortable and clean. It was a wonderful vacation! Thank you! "
United States
Barbara
$547 nightly
The price is $575
Dec 12 - Dec 13
Total with taxes and fees
Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7
Property grounds
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
East End
9.6 out of 10, Exceptional, (46)
"Great place "
United States
Christine
$312 nightly
The price is $331
Dec 15 - Dec 16
Total with taxes and fees
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
On the beach
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1

Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1

Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
Captiva
7.8 out of 10, Good, (12)
"Loved being right on the beach! Such a great little place!"
United States
Bryant
$484 nightly
The price is $508
Dec 12 - Dec 13
Total with taxes and fees
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
Beach nearby, sun loungers, beach towels
Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach.

Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach.

Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach.
Mid Island
10.0 out of 10, Exceptional, (101)
"Was a great family vacation! Short walk to the beach and had all the chairs and cart available to use, pool was awesome for the kids!!"
United States
Chase H.
$492 nightly
The price is $543
Dec 12 - Dec 13
Total with taxes and fees
Gorgeous Blue Lagoon. An oasis just 2 min walk from the beach.
Terrace/patio
720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6.

720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6.

720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6.
4.0 star property
Fort Myers Beach
9.6 out of 10, Exceptional, (29)
"It was a great place. Wish we had had more time there!"
United States
Fred M.
$510 nightly
The price is $563
Dec 14 - Dec 15
Total with taxes and fees
720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6.
Pool
NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (41)
"My wife and I loved our stay at Waterside. The property was clean and well appointed. The area was nice and we loved walking up to the local watering hole for sunset views. I would recommend it highly. "
United States
Ron R.
$337 nightly
The price is $371
Dec 15 - Dec 16
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage
On the beach
Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6

Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6

Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6
Captiva
9.6 out of 10, Exceptional, (8)
"Very nice stay. Loved the easy access to the beach and our unit was great."
United States
Juan
$628 nightly
The price is $664
Dec 12 - Dec 13
Total with taxes and fees
Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6
Terrace/patio
Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ

Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ

Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
Fort Myers Beach
10.0 out of 10, Exceptional, (20)
"What a lovely place we rented, soo close to the Beach and everything else we needed. The apt/home has been remodeled and it was Very cute. We enjoyed our stay and would love to rent this place again. Thank you again to Sandy for all of the help in answering questions and making our stay perfect. 😎"
United States
Robin B.
$426 nightly
The price is $470
Dec 14 - Dec 15
Total with taxes and fees
Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
On the beach
Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4

Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4

Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4
Captiva
8.6 out of 10, Excellent, (9)
"Great spot. Amazing location"
United States
Brandon C.
$599 nightly
The price is $635
Dec 12 - Dec 13
Total with taxes and fees
Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4
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 Tradewinds Hotel Reviews

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

10/10 Excellent
"Wonderful place to stay, great location and very clean! Penny at the front desk is super helpful and welcoming! :)"
Rebecca L. 3-night trip
Posted 1 day ago
Matanzas Inn Bayside Resort and Marina

Frequently asked questions

What can I expect on my historical trip to Tradewinds?
You'll probably want to seek out the historically relevant sites while you're staying in Tradewinds. You'll probably want to also explore the many sights while you're visiting the area.
How many historically relevant hotels are located in Tradewinds?
In Tradewinds, there are 23 hotels and other accommodations bookable on Expedia though you won't find many designated historic hotels.
What are the most important historical sites and other places in Tradewinds?
A favorite place to visit is J. N. Ding Darling National Wildlife Refuge. Additionally, you'll find Key West Express in the area.
What is a historic hotel like in Tradewinds?
Historic hotels give guests the chance to stay in a place officially recognized with a national historic designation. Historic hotels throughout the world can be castles, palaces or even pubs or old police stations. These types of hotels in Tradewinds typically retain original qualities like traditional architecture and period features in their public spaces or guestrooms.
What is the difference between a historic hotel and a heritage hotel?
They are quite similar. "Historic hotel" is more commonly used in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to put more importance on the building and architecture itself. Heritage hotels draw their meaning mainly from the place's cultural value and how it shaped the community.
Do historic hotels in Tradewinds have modern facilities?
Yes, efforts are made to preserve historic facades and treasured traditions, but interiors include modern conveniences and safety features. Tourists who book a stay can expect the usual amenities you'd find in a hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. Booking a historic hotel in Tradewinds doesn't mean you're picking a place that's uncomfortable for guests or simply rundown.

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