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Fleming Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Fleming Key vacation rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$311 nightly
The price is $349
Nov 15 - Nov 16
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A wooden signpost with city names and distances in miles.

2. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (463 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
$236 nightly
The price is $262
Nov 18 - Nov 19
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
A pathway leading to a covered outdoor seating area with a table and chairs, surrounded by lush greenery and trees.

3. Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (44 reviews)
"Great stay! "
United States
Victoria T.
$364 nightly
The price is $406
Nov 4 - Nov 5
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
A pool area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

4. Leo's Lodge | Newly Updated!

Leo's Lodge | Newly Updated!
Old Town Key West
9.0 out of 10, Wonderful, (40 reviews)
"Very nice place to stay, great pool area and great room. "
United States
Blake
$290 nightly
The price is $325
Nov 8 - Nov 9
Total with taxes and fees
Leo's Lodge | Newly Updated!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

5. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Old Town Key West
9.8 out of 10, Exceptional, (17 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
$296 nightly
The price is $328
Dec 1 - Dec 2
Total with taxes and fees
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
A small, private entrance to a house with a brick pathway leading to a door.

6. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Ricky’s Retreat is in a fantastic location. The room was all you need in Key West. Highly recommend it and will definitely stay there again."
United States
Brian R.
$343 nightly
The price is $382
Nov 16 - Nov 17
Total with taxes and fees
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A narrow brick pathway flanked by white buildings with potted plants and a bench.

7. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Old Town Key West
9.8 out of 10, Exceptional, (27 reviews)
"Awesome location & very helpful host!"
United States
Jay M.
$314 nightly
The price is $352
Nov 8 - Nov 9
Total with taxes and fees
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
A tropical garden pathway leading to a building with a yellow facade and green shutters.

8. 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, (115 reviews)
"Absolutely perfect! Great location, great property and great unit. Beautiful pool area with ice machine and filtered water dispenser was a highlight for the very hot and humid time we visited. Would return immediately and stay in the same spot. Thank you for a very enjoyable time in Key West!"
United States
Justin D.
$327 nightly
The price is $363
Dec 1 - Dec 2
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A covered porch with white wooden railings, wicker furniture, and hanging lanterns.

9. Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (81 reviews)
"Fantastic location"
United States
Jennifer
$421 nightly
The price is $472
Nov 9 - Nov 10
Total with taxes and fees
Duval Delight | Recently Remodeled Condo on Duval!
A spacious kitchen with a large island, a dining area with a view, and a balcony with a view.

10. Waterfront Dock Pool Key West Near Duval

Waterfront Dock Pool Key West Near Duval
Meadows
10.0 out of 10, Exceptional, (41 reviews)
"Clean, comfy and had everything we expected."
United States
Chrystalbelle R.
$375 nightly
The price is $418
Nov 8 - Nov 9
Total with taxes and fees
Waterfront Dock Pool Key West Near Duval
A multi-level wooden house with a blue staircase and white railings.

11. Underwater Cabana at Custom House Inn | On Duval!

Underwater Cabana at Custom House Inn | On Duval!
Key West Historic District
9.8 out of 10, Exceptional, (27 reviews)
"We had a great comunication with the host. They were very responsive to all my questions and concerns. The check in process was very easy. They helped me with my car and shuttled me to the unit. The place was right on Duval Street. Although like that not very noisy as it was at the back. You could be in your room and at the bar for music and drinks in a minute. The room was comfortable and clean. If I go back to Key West again, I will not look for any other place to stay than Custom House."
United States
EMIN
$396 nightly
The price is $442
Nov 10 - Nov 11
Total with taxes and fees
Underwater Cabana at Custom House Inn | On Duval!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

12. 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, (139 reviews)
"Great place to stay"
United States
walter l.
$336 nightly
The price is $373
Nov 10 - Nov 11
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

13. Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (47 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
$290 nightly
The price is $325
Nov 15 - Nov 16
Total with taxes and fees
Chagall's Corner | Newly Remodeled!
A wooden deck with a large tree, outdoor seating, and a marina in the background.

14. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
$251 nightly
The price is $281
Nov 9 - Nov 10
Total with taxes and fees
Poolside Cottage #412
A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

15. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.8 out of 10, Exceptional, (22 reviews)
"Great facility and loved the location! "
United States
Matt R.
$421 nightly
The price is $472
Nov 21 - Nov 22
Total with taxes and fees
The Grand Cayman | Beautifully Remodeled Key West!
An outdoor patio area with wooden furniture, a large tree, and lush greenery.

16. Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!

Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
Key West Historic District
9.6 out of 10, Exceptional, (37 reviews)
"Everything was fantastic, great location to the North end of Duval St."
United States
Brett W.
$416 nightly
The price is $466
Nov 15 - Nov 16
Total with taxes and fees
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
A building with a red door, a covered porch, and a bamboo plant in the foreground.

17. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
United States
BARBARA Y.
$376 nightly
The price is $422
Nov 15 - Nov 16
Total with taxes and fees
Road's End | Prime Old Town Location! Updated Home w/ Pool
A narrow pathway leading to a house with a blue exterior, a number '12' sign, and various potted plants.

18. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
10.0 out of 10, Exceptional, (123 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.
$349 nightly
The price is $387
Nov 18 - Nov 19
Total with taxes and fees
Studio Blu - Historic Key West Studio + Bikes
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

19. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
$280 nightly
The price is $313
Dec 1 - Dec 2
Total with taxes and fees
Poolside Cottage #411
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

20. 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.
$421 nightly
The price is $472
Nov 9 - Nov 10
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
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.
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Top Fleming Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

8/10 Good
"No desk area in room and shower and did not work. And very slow drain."
Kevin 2-night trip
Posted 3 hours ago
Casa Marina Key West, Curio Collection by Hilton

Find out more about Fleming Key

Everything you need to know about Fleming Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fleming Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Fleming Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fleming Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Fleming Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $262 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Fleming Key rentals

At Expedia, we put the best Fleming Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Fleming Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fleming Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fleming Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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