Stock Island Hotel Guide - Hotels with Pool in Stock Island, Key West
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Our top choices for Stock Island hotels with a pool
8.8 out of 10, Excellent, (1753)
"The place is great!"
Anna
The price is €286
includes taxes & fees
4 Jan - 5 Jan 2026
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location.
The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating.
I hope it’s available for our next trip."
Julie
The price is €447
includes taxes & fees
4 Jan - 5 Jan 2026
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to DowntownStock Island
10.0 out of 10, Exceptional, (1)
"The owners are very attentive and interested in making sure that our stay was great on every level. Top notch communication and they went above and beyond with the hospitality. Thanks so much. "
Marc B.
The price is €347
includes taxes & fees
5 Jan - 6 Jan 2026
Wake up aboard your private yacht by Luxury Sea Charters in Key West - One Heart
Wake up aboard your private yacht by Luxury Sea Charters in Key West - One HeartStock Island
10.0 out of 10, Exceptional, (2)
"Absolutely amazing place to stay… better than we imagined! The host, Tom was fantastic and made us feel right at home. We loved the views and the amenities, Truely an awesome place to stay!"
John C.
The price is €311
includes taxes & fees
4 Jan - 5 Jan 2026
Wake up Aboard your private yacht by Luxury Sea Charters in Key West - FREE TIME
Wake up Aboard your private yacht by Luxury Sea Charters in Key West - FREE TIMEStock Island
10.0 out of 10, Exceptional, (1)
"Tom & Jen were great hosts! Prompt with communication before and during our stay. They shopped for and delivered our groceries, along with welcoming us with a tour of the marina & boat. Very personable. The boat was very clean with all necessities on board. Highly recommend staying aboard Free Time!"
Melissa G.
The price is €715
includes taxes & fees
4 Jan - 5 Jan 2026
The price is €496
includes taxes & fees
24 Jan - 25 Jan 2026
Grand Marina Suite - Poolside & Waterfront Condo
Grand Marina Suite - Poolside & Waterfront CondoStock Island
9.6 out of 10, Exceptional, (29)
"2nd time staying here. Love the location and the facilities. Perfect for boating and fishing. The marina is next door so its very convenient. Good times"
robert s.
The price is €476
includes taxes & fees
5 Jan - 6 Jan 2026
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!Stock Island
10.0 out of 10, Exceptional, (37)
"Checkin couldn't be easier. The place looks new and the furniture is comfortable. It had everything we needed. Located on stock island, it's a short drive to key west. There are plenty of good restaurants close by and cvs is a mile away."
Timothy K.
The price is €881
includes taxes & fees
19 Jan - 20 Jan 2026
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 Stock Island Hotel Reviews
The Reach Key West, Curio Collection by Hilton
10/10 Excellent
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