Default HTG hotel image

Search Fleming Key Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Fleming Key cottages

A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

1. OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.4 out of 10, Exceptional, (63 reviews)
"We had such a great time on our visit. The place was exactly like the only photos and we enjoyed the pool, the area and the other visiters. Beautiful Old Town feel!"
United States
Debra S.
OSPREY STUDIO @ The Colony-Sleeps up to 4
A patio with a grill, yellow chairs, and a table under a blue umbrella, surrounded by a wooden deck and a lattice fence.

2. HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (102 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
$553 nightly
The price is $605
Sep 30 - Oct 1
Total with taxes and fees
HIDDEN OASIS 3 blocks from Duval
A two-story building with balconies, surrounded by lush greenery and palm trees.

3. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (34 reviews)
"Jolly Rooster cottage was a prefect and great location. Cottage was very clean. We had a great girls trip!We will definitely be back."
United States
Phyllis B.
$521 nightly
The price is $580
Sep 23 - Sep 24
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

4. Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Great location, clean and well equipped."
United States
Richard M.
$577 nightly
The price is $631
Sep 14 - Sep 15
Total with taxes and fees
Find your zen at HIDDEN TREASURE
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fleming Key Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"Na"
David 7-night trip
Posted less than an hour ago
Blue Flamingo Resort Key West

Find out more about Fleming Key

Fleming Key Cottages information

Number of reviews
136
Accommodation
53 Cottages
Lowest Price
$580
Highest Price
$631

Frequently asked questions

Why book your cottage in Fleming Key with Expedia?
Expedia has some superb cottages in Fleming Key, so start packing for a memorable stay on nature's doorstep. If you have a budget, choose how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Fleming Key?
With Expedia's convenient filter tool, getting your hands on cheap cottages in Fleming Key couldn't be simpler. To find properties that'll make your bank balance smile, narrow down your search by star rating, budget and amenities.

Explore a world of travel with Expedia