Fleming Key, FL

Travel Guide

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$587 nightly
The price is $660 total per night from Mar 4 to Mar 5
$660 total
Mar 4 - Mar 5
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (3,071 reviews)
Clean room everything was very nice

Reviewed on Feb 15, 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$410 nightly
The price is $461 total per night from Mar 5 to Mar 6
$461 total
Mar 5 - Mar 6
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
8/10 Very Good! (2,075 reviews)
Were given a free upgrade, room was very nice, staff was responsive, place was in good shape

Reviewed on Feb 15, 2026

Ibis Bay Beach Resort
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$418 nightly
The price is $471 total per night from Mar 11 to Mar 12
$471 total
Mar 11 - Mar 12
Total with taxes and fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,809 reviews)
Oceans Edge was amazing! Super friendly staff, impeccably clean property, rooms, on site restaurant with delicious food and drinks, etc.. I would book again the next time we come back to Key West! Thanks for the hospitality and great time!

Reviewed on Feb 16, 2026

Oceans Edge Key West Resort, Hotel & Marina
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.
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy Key West FL
Stay at this houseboat in Key West. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Duval ...
8.8/10 Excellent! (178 reviews)
Extremely clean

Reviewed on Feb 11, 2026

Aqua Lodges at Hurricane Hole Marina
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3 out of 5
1445 S Roosevelt Blvd Key West FL
Stay at this condo in Key West. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Duval ...
8.2/10 Very Good! (824 reviews)
Clean, friendly and convenient

Reviewed on Feb 9, 2026

Coconut Mallory Resort And Marina By Kees Vacations
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

Key West FL
Stay at this cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (150 reviews)
The host, the home and the location - win, win, win!!!

Reviewed on Feb 10, 2026

Heart of Downtown Key West Cottage With Off-Street Parking
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.

Cities near Fleming Key

Explore a world of travel with Expedia