A sunset over a coastal landscape with a small island surrounded by water.

Find Historic Hotels in Stock Island, FL

  • 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 Stock Island Historic Hotels

Our top choices for Stock Island historic hotels

Marina

Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!

Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!
Stock Island
9.4 out of 10, Exceptional, (43 reviews)
"Great Stay"
United States
Denton S.
The price is AED 826
AED 1,398 total
includes taxes & fees
30 Jul - 31 Jul
Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!
Property grounds

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is AED 992
AED 2,174 total
includes taxes & fees
23 Jul - 24 Jul
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Exterior detail

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

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (122 reviews)
"Very communicative, property was as pictured and bikes were perfect for getting around. We didn’t need a car but had no trouble parking right next to the front door. Sandy’s had the best coffee and food was delicious! Will definitely come again!"
United States
Emily F.
The price is AED 650
AED 1,385 total
includes taxes & fees
5 Aug - 6 Aug
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Beach

Summer special@ 129 July, Aug. Sun thru Wed.ngts lodging only 129 + extras

Summer special@ 129 July, Aug. Sun thru Wed.ngts lodging only 129 + extras
Old Town Key West
9.6 out of 10, Exceptional, (253 reviews)
"Loved our stay here!"
United States
Kristin E.
The price is AED 511
AED 1,230 total
includes taxes & fees
8 Aug - 9 Aug
Summer special@ 129 July, Aug. Sun thru Wed.ngts lodging only 129 + extras
Outdoor pool

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (126 reviews)
"Great little house for a family "
United States
Edward M.
The price is AED 2,204
AED 5,209 total
includes taxes & fees
20 Aug - 21 Aug
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Terrace/patio

CLARO ~ Adults Only, Pool View King Room in Azul Mansion!

CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
Old Town Key West
9.8 out of 10, Exceptional, (161 reviews)
"Very convenient and extremely comfortable!"
United States
Bill B.
The price is AED 386
AED 998 total
includes taxes & fees
18 Aug - 19 Aug
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
Beach towels

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
9.8 out of 10, Exceptional, (46 reviews)
"Great location, one block from Duval Street but still quiet, clean and comfortable. "
United States
Jackie H.
The price is AED 704
AED 1,793 total
includes taxes & fees
2 Aug - 3 Aug
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Pool

Poolside Paradise - Heated Pool & Steps to Duval St

Poolside Paradise - Heated Pool & Steps to Duval St
Old Town Key West
8.8 out of 10, Excellent, (24 reviews)
"Great location"
United States
Peter S.
Poolside Paradise - Heated Pool & Steps to Duval St
Pool

Two Bedroom Two Bath Balcony Villa Steps from Duval!

Two Bedroom Two Bath Balcony Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (46 reviews)
"Location was great. Facility and rooms were clean. Great amenities - we will book again"
United States
William P.
The price is AED 1,649
AED 2,090 total
includes taxes & fees
9 Aug - 10 Aug
Two Bedroom Two Bath Balcony Villa Steps from Duval!
A heated pool

Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (60 reviews)
"The property was more than expected. The hosts were wonderful people, and they thought of everything to make it an enjoyable stay."
United States
Glenn E.
The price is AED 1,466
AED 1,858 total
includes taxes & fees
27 Jul - 28 Jul
Two Bedroom Two Bath Poolside Villa Steps from Duval!
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

Top Stock Island Hotel Reviews

Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Perfectly clean, very helpful staff, nice place, great drinks and food, and the pool is very good to stay and chill. Also, pretty close to important places to visit at Key West."
Jimmy 1-night trip
Posted less than an hour ago
Ibis Bay Beach Resort

Explore a world of travel with Expedia