Default HTG hotel image

Search and Rent Fleming Key Condos

  • 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 condo rentals

A tropical garden pathway leading to a building with a yellow facade and green shutters.

1. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (111 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property was just as listed. Very clean, quiet, the pool was very refreshing! Great location, walkable to almost anything. Would highly recommend!"
United States
Chris & Sarah F.
$263 nightly
The price is $292
Sep 7 - Sep 8
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A spacious living room with a large flat-screen TV, a teal sofa, a coffee table, and a view of the ocean through large windows.

2. Waterfront Dock Pool Condo Near Duval St Pet OK

Waterfront Dock Pool Condo Near Duval St Pet OK
Meadows
9.6 out of 10, Exceptional, (46 reviews)
"Hosts are super responsive and helpful. Perfect location. Would absolutely stay here again! "
United States
Amber G.
$321 nightly
The price is $356
Sep 7 - Sep 8
Total with taxes and fees
Waterfront Dock Pool Condo Near Duval St Pet OK
A tropical garden pathway leading to a building with a yellow facade and green shutters.

3. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (136 reviews)
"Great place to stay"
United States
walter l.
$289 nightly
The price is $321
Sep 15 - Sep 16
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A marina with boats docked, a clear sky, and a rainbow.

4. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! Beautiful view. No complaints. Easy check in and great communication with owner. Thanks for a great trip!"
United States
Haley P.
$321 nightly
The price is $356
Sep 8 - Sep 9
Total with taxes and fees
Waterfront Condo Dock Pool Near Duval St
A Victorian-style building with a prominent tower, multiple balconies, and a red-tiled roof.

5. La Casa de Luna - 1 Bd/1B condo just off upper Duval

La Casa de Luna - 1 Bd/1B condo just off upper Duval
Old Town Key West
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful stay! Very communicative and helpful. "
United States
Debbie H.
La Casa de Luna - 1 Bd/1B condo just off upper Duval
A spacious kitchen with a large island, a dining area with a view, and a balcony with a view.

6. Waterfront Dock Pool Key West Near Duval

Waterfront Dock Pool Key West Near Duval
Meadows
10.0 out of 10, Exceptional, (37 reviews)
"We loved our stay! Beautiful room with a wonderful view. We loved how quiet and relaxing it was!"
United States
Jesse B.
$360 nightly
The price is $400
Sep 13 - Sep 14
Total with taxes and fees
Waterfront Dock Pool Key West Near Duval

7. Turtle Nest Condo + Pool / 2nd Floor

Turtle Nest Condo + Pool / 2nd Floor
Key West Historic District
$271 nightly
The price is $301
Sep 8 - Sep 9
Total with taxes and fees
Turtle Nest Condo + Pool / 2nd Floor
A narrow stone pathway flanked by a yellow building with a white fence and a wall-mounted electrical box.

8. Hidden Key West Cottage - Walk to Duval !!!

Hidden Key West Cottage - Walk to Duval !!!
Old Town Key West
10.0 out of 10, Exceptional, (3 reviews)
"Host was great! Fast response and easy to work with. Very, very, very clean! Quiet area A"
United States
Regina E.
$248 nightly
The price is $276
Sep 22 - Sep 23
Total with taxes and fees
Hidden Key West Cottage - Walk to Duval !!!
A two-story house with a white picket fence, a covered porch, and a small garden area with plants and a palm tree.

9. Sea Breeze - One Block from Duval Street

Sea Breeze - One Block from Duval Street
Old Town Key West
9.4 out of 10, Exceptional, (55 reviews)
"Great location. Clean house. Loved my stay here. "
United States
Alan K.
$483 nightly
The price is $538
Sep 20 - Sep 21
Total with taxes and fees
Sea Breeze - One Block from Duval Street
A pool area with a wooden fence, lounge chairs, and a bar.

10. Duval Street Suites on Duval Free Parking and heated Pool

Duval Street Suites on Duval Free Parking and heated Pool
Old Town Key West
10.0 out of 10, Exceptional, (18 reviews)
"Location was perfect!"
United States
David C.
$218 nightly
The price is $243
Sep 16 - Sep 17
Total with taxes and fees
Duval Street Suites on Duval Free Parking and heated Pool
A two-story building with a balcony, storefronts, and a sign for 'Frangipani Gallery'.

11. Escape to the wonderful Cuban Paradise!

Escape to the wonderful Cuban Paradise!
Old Town Key West
9.6 out of 10, Exceptional, (145 reviews)
"clean, great location"
United States
jessica l.
Escape to the wonderful Cuban Paradise!
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

12. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
$434 nightly
The price is $482
Sep 4 - Sep 5
Total with taxes and fees
The Cat Island Suite | Charmingly Renovated w/ Pool
A cozy living room with a sofa, two chairs, a coffee table, a TV, and a ceiling fan.

13. Sky Loft - Steps from Duval Street & Shared Pool

Sky Loft - Steps from Duval Street & Shared Pool
Old Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Nice place with a great location. Ceilings are a little low for taller people."
United States
Andrew C.
$422 nightly
The price is $469
Sep 20 - Sep 21
Total with taxes and fees
Sky Loft - Steps from Duval Street & Shared Pool
A coastal hotel with multiple-story buildings, palm trees, and a well-maintained garden.

14. Heated Rooftop Pool, Gated Parking - Casa Caribe

Heated Rooftop Pool, Gated Parking - Casa Caribe
Old Town Key West
8.8 out of 10, Excellent, (28 reviews)
"We loved our stay! Perfect location to Duval Street."
United States
Theresa N.
$621 nightly
The price is $690
Sep 8 - Sep 9
Total with taxes and fees
Heated Rooftop Pool, Gated Parking - Casa Caribe
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

15. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
$433 nightly
The price is $481
Sep 12 - Sep 13
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A swimming pool surrounded by lush greenery, with lounge chairs and a covered seating area.

16. COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.4 out of 10, Exceptional, (119 reviews)
"Excellent stay, great location! "
United States
Dr. Christopher S.
$289 nightly
The price is $321
Sep 10 - Sep 11
Total with taxes and fees
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

17. Pool View Suite | Beachside Resort

Pool View Suite | Beachside Resort
Key West
8.0 out of 10, Very Good, (3 reviews)
"It was a holiday weekend. Key West in general all lodging was expensive. The room was very comfortable and clean. More than enough room. I was on the water which was amazing. The pool area was very awesome. Love that they have a bar and restaurant available. All the available excursions. I took advantage of the Sunset Tour. Property manager was available for any questions. Beachside staff was also very helpful. Would definitely visit again. Great Experience!! Thank you."
United States
Christie Y.
$270 nightly
The price is $300
Sep 7 - Sep 8
Total with taxes and fees
Pool View Suite | Beachside Resort
A swimming pool area with multiple pools, palm trees, lounge chairs, and a clear blue sky.

18. Atlantic Parrot | Oceanfront Condo w/ Pool

Atlantic Parrot | Oceanfront Condo w/ Pool
Beachside
9.8 out of 10, Exceptional, (8 reviews)
"Absolutely beautiful property as well as room I loved it everything about it was beautiful "
United States
Misty C.
$670 nightly
The price is $744
Sep 9 - Sep 10
Total with taxes and fees
Atlantic Parrot | Oceanfront Condo w/ Pool
A pool surrounded by palm trees and a building with a green roof.

19. The Barbados | Private Balcony, Pool View!

The Barbados | Private Balcony, Pool View!
Key West
9.8 out of 10, Exceptional, (11 reviews)
"Great trip"
United States
Doug P.
$420 nightly
The price is $467
Sep 4 - Sep 5
Total with taxes and fees
The Barbados | Private Balcony, Pool View!
A wooden deck with a thatched roof structure, a pool, lounge chairs, and a bar area.

20. Waterfront Condo | Pool, Dock, Parking, Sleeps 8

Waterfront Condo | Pool, Dock, Parking, Sleeps 8
Meadows
9.8 out of 10, Exceptional, (39 reviews)
"We always love staying at Pelicans Landing. This is the first time in this specific condo. It was very nice. We love being able to see the pool and water. We would highly suggest staying here. We have always had good communications with the property managers/host. "
United States
Lorie C.
$351 nightly
The price is $391
Sep 7 - Sep 8
Total with taxes and fees
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
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

Southwinds Motel

Southwinds Motel

10/10 Excellent
"Southwinds Motel has to be the absolute best spot I’ve stayed at when it comes to conveniences on site along with an awesome location and proximity to sites and activities. Perfectly located around the Southernmost part of Key West, Southwinds gives you fully stocked bar WITH a built-in liquor store. Super convenient off rip. Bar has live music in the afternoon and evening, a pretty nice pool and deck area and, what I really found most convenient, access to rentals for any means of transportation you need for Key West from bicycles to scooters to full sized golf carts. Rentals are provided by Bone Island rentals who also deliver your mode of moving around to the property and picks it up from the property. A totally ‘Key West’ luxury in my mind. So you’re not staying in the fanciest of shindigs, but you rented a motel because you probably plan to be out and about in beautiful Key West and not cooped up, so you most definitely shouldn’t have grand expectations, but you definitely won’t be disappointed with the digs either. Another thing I really appreciated was after check-in, we were also gifted 2 vouchers for free specialty cocktails from their bar. It was small drinks and only their specialty drinks but still complimentary, so we say thank you and enjoy. They let us combine both tickets for one full sized rum runner my wife enjoyed. Overall 10/10 for comfort, convenience, location and it’s vibe. Will absolutely be going back and 100 percent recommend to all staying in KW"
Juan 4-night trip
Posted 1 hour ago
Southwinds Motel

Find out more about Fleming Key

Fleming Key Condo Rentals information

Number of reviews
594
Accommodation
428 Condo Rentals
Lowest Price
$243
Highest Price
$744

Frequently asked questions

Why book your condo in Fleming Key with Expedia?
Expedia will help you find your ideal condo in Fleming Key. On the lookout for an upmarket stay? Make use of our filters to search for properties that have a 5-star rating. If you have a fixed budget, select how much you want to spend and then check out our incredible deals. We'll help you find a suitable stay whatever your plans or bank balance.
How can I find cheap condos in Fleming Key?
A wonderful way to uncover cheap condos in Fleming Key is with Expedia's filter tool. Narrow down your search results by amenities, star rating and budget to secure excellent rates in a couple of clicks.

Explore a world of travel with Expedia