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Fleming Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Fleming Key vacation rentals

A wooden signpost with city names and distances in miles.

1. 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, (451 reviews)
"Clean comfortable and close too many attractions."
United States
Mark A.
$205 nightly
The price is $228
Sep 7 - Sep 8
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

2. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$235 nightly
The price is $264
Aug 31 - Sep 1
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
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.
$255 nightly
The price is $283
Aug 31 - Sep 1
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A pool area with a wooden deck, a two-story building with balconies, and palm trees.

4. 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, (56 reviews)
"The room was exactly what we expected, clean, cozy and a good place to chill after a day of adventuring in Key West. The pool/hot tub was wonderful and I wish I had one at home we didn’t want to leave and can’t wait to be back!"
United States
Cody S.
$319 nightly
The price is $354
Aug 31 - Sep 1
Total with taxes and fees
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

5. VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (56 reviews)
"Nice clean apartment and good walking distance to Old Town restaurants and neighborhood."
United States
Justin R.
$310 nightly
The price is $344
Aug 31 - Sep 1
Total with taxes and fees
VanGogh Studio | Updated, Old Town, Heated Pool
A tropical garden pathway leading to a building with a yellow facade and green shutters.

6. 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, (110 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.
$255 nightly
The price is $283
Aug 31 - Sep 1
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A kitchen with a refrigerator, stove, and two bar stools.

7. Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
$259 nightly
The price is $288
Aug 31 - Sep 1
Total with taxes and fees
Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
A small, private entrance to a house with a brick pathway leading to a door.

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (39 reviews)
"Fantastic and cozy… and surprisingly right in the middle of Key West fun"
United States
Jay R.
$353 nightly
The price is $392
Aug 31 - Sep 1
Total with taxes and fees
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A marina with boats docked, a clear sky, and a rainbow.

9. 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.
$352 nightly
The price is $391
Sep 2 - Sep 3
Total with taxes and fees
Waterfront Condo Dock Pool Near Duval St
A hotel room with two beds, a ceiling fan, a TV, and a window with blinds.

10. Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (46 reviews)
"Great location"
United States
Glen V.
$364 nightly
The price is $403
Sep 1 - Sep 2
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
A narrow alleyway with white buildings, a stone pathway, and various plants.

11. Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Old Town Key West
9.6 out of 10, Exceptional, (38 reviews)
"Very clean and comfortable. Great location. I would definitely stay here again. "
United States
Dawn R.
$352 nightly
The price is $390
Sep 14 - Sep 15
Total with taxes and fees
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
A modern living room with a grey sofa, wooden flooring, a ceiling fan, and framed artwork on the walls.

12. Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!
Old Town Key West
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay!"
United States
Andrew M.
$434 nightly
The price is $482
Aug 31 - Sep 1
Total with taxes and fees
Kingfish Keep | Lively Escape on Duval! Balcony!
A pathway leading to a house with a number '121' on the wall, surrounded by potted plants.

13. Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (122 reviews)
$303 nightly
The price is $336
Aug 31 - Sep 1
Total with taxes and fees
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

14. Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (45 reviews)
"Great pool. Wonderful location."
United States
Anonymous traveler
$317 nightly
The price is $352
Aug 31 - Sep 1
Total with taxes and fees
Chagall's Corner | Newly Remodeled!
A pool area with a pool, lounge chairs, and a building with a porch.

15. Hollinsed House Studio - Great Location!!

Hollinsed House Studio - Great Location!!
Old Town Key West
9.6 out of 10, Exceptional, (162 reviews)
"Perfect location, nice spot for a long weekend getaway. "
United States
Charlene B.
$428 nightly
The price is $475
Sep 20 - Sep 21
Total with taxes and fees
Hollinsed House Studio - Great Location!!
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

16. Claude Monet Suite | Cozy Studio with Pool & Patio

Claude Monet Suite | Cozy Studio with Pool & Patio
Old Town Key West
9.4 out of 10, Exceptional, (38 reviews)
"We had a great stay- The property is exactly as described. Location was convenient and easy to get around by foot or scooter. The neighborhood was quiet and parking was not a problem. We will definitely stay here again!"
United States
Sara F.
$340 nightly
The price is $377
Sep 19 - Sep 20
Total with taxes and fees
Claude Monet Suite | Cozy Studio with Pool & Patio
A modern kitchen with white cabinetry, black countertops, a stainless steel sink, and a view of the outdoors.

17. Waterfront Condo Dock Pool Downtown Near Duval

Waterfront Condo Dock Pool Downtown Near Duval
Meadows
9.6 out of 10, Exceptional, (29 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.
$363 nightly
The price is $403
Aug 31 - Sep 1
Total with taxes and fees
Waterfront Condo Dock Pool Downtown Near Duval
A tropical garden pathway leading to a building with a yellow facade and green shutters.

18. SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community Pool!

SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community Pool!
Old Town Key West
9.8 out of 10, Exceptional, (113 reviews)
"Wonderful experience"
United States
Bernado
$312 nightly
The price is $346
Aug 31 - Sep 1
Total with taxes and fees
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community Pool!
A covered porch with white wooden railings, wicker furniture, and hanging lanterns.

19. Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (73 reviews)
"Great stay"
United States
Lisa H.
$454 nightly
The price is $504
Aug 31 - Sep 1
Total with taxes and fees
Duval Delight | Recently Remodeled Condo on Duval!
A two-story house with a white picket fence, a covered porch, and a small garden area with plants and a palm tree.

20. 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.
$522 nightly
The price is $579
Sep 15 - Sep 16
Total with taxes and fees
Sea Breeze - One Block from Duval Street
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

Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Todo Super bien; el personal que trabaja en la instalación te hacen sentir como en casa muy acogedor; tranquilo y un servicio increíble"
Lenier 1-night trip
Posted 4 hours ago
Ibis Bay Beach Resort

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 $228 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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