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Our top choices for Fleming Key holiday rentals

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
The price is £216
includes taxes & fees
10 Nov - 11 Nov
Aqua Lodges at Hurricane Hole Marina

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.
The price is £203
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!

3. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (58 reviews)
"The room was functional. We loved the location and ease of getting everywhere. The pool was really nice. The only complaint is that the entire bathroom floods when you take a shower. We ended up using our flip flops to squeegee the water to the drain, because the drain is higher than the rest of the floor. Highly recommend providing a squeegee to help with flooding."
United States
Shawn
The price is £255
includes taxes & fees
11 Nov - 12 Nov
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

4. 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.
The price is £304
includes taxes & fees
20 Nov - 21 Nov
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

5. Waterfront Condo Dock Pool Downtown Near Duval

Waterfront Condo Dock Pool Downtown Near Duval
Meadows
9.6 out of 10, Exceptional, (30 reviews)
"Wow, this was one of the best short term rentals we've done. Well appointed, extremely clean, convenient location, and everything pretty much top of the line."
United States
John L.
The price is £329
includes taxes & fees
29 Nov - 30 Nov
Waterfront Condo Dock Pool Downtown Near Duval

6. 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
9.6 out of 10, Exceptional, (18 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
The price is £235
includes taxes & fees
1 Dec - 2 Dec
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
10.0 out of 10, Exceptional, (41 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.
The price is £278
includes taxes & fees
16 Nov - 17 Nov
Ricky's Retreat - Truman @ Duval | Ideal Getaway!

8. Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool
Old Town Key West
9.0 out of 10, Wonderful, (25 reviews)
"Super cute place. "
United States
Amanda M.
The price is £249
includes taxes & fees
23 Nov - 24 Nov
Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

9. 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.
The price is £259
includes taxes & fees
10 Nov - 11 Nov
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

10. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is £235
includes taxes & fees
3 Dec - 4 Dec
Poolside Cottage #412

11. 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
The price is £363
includes taxes & fees
11 Nov - 12 Nov
Duval Delight | Recently Remodeled Condo on Duval!

12. 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.
The price is £272
includes taxes & fees
16 Nov - 17 Nov
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

13. 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.
The price is £275
includes taxes & fees
1 Dec - 2 Dec
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

14. 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
The price is £332
includes taxes & fees
10 Nov - 11 Nov
Underwater Cabana at Custom House Inn | On Duval!

15. 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.
The price is £255
includes taxes & fees
15 Nov - 16 Nov
Chagall's Corner | Newly Remodeled!

16. 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)
"Excellent property and the communication with the hosts was excellent. Love that they offered complimentary pickup from the airport to the property too."
United States
Mike C.
The price is £330
includes taxes & fees
15 Nov - 16 Nov
Road's End | Prime Old Town Location! Updated Home w/ Pool

17. 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.
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!

18. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is £235
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #411

19. Duval Hideaway | Dog-Friendly w/ Shared Hot Tub

Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
Old Town Key West
9.6 out of 10, Exceptional, (30 reviews)
"Close to everything ! It was a perfect location and we loved the hot tub. Amazing that it came with a parking spot. Would stay again."
United States
Jenn O.
The price is £363
includes taxes & fees
6 Dec - 7 Dec
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub

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.
The price is £361
includes taxes & fees
10 Nov - 11 Nov
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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Find out more about Fleming Key

Everything you need to know about Fleming Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Fleming Key holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fleming Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fleming Key holiday rentals we have selected for you start as low as £202 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Fleming Key rentals

At Expedia, we put the best Fleming Key holiday 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 holiday.

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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