Fleming Key Holiday Rentals
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Our top choices for Fleming Key holiday rentals
1. Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole MarinaStock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
Kagni
The price is HK$1,193
HK$2,698 total
includes taxes & fees
16 Nov - 17 Nov
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, (464 reviews)
"We liked sitting by the pool and visiting with other guests. The air conditioner struggled to keep the room cool; it ran all night long to maintain 72 degrees."
Karen
The price is HK$981
HK$2,142 total
includes taxes & fees
2 Dec - 3 Dec
3. 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."
Brian R.
The price is HK$1,065
HK$2,978 total
includes taxes & fees
14 Dec - 15 Dec
4. Living the Dream Key West Style
Living the Dream Key West StyleStock Island
10.0 out of 10, Exceptional, (64 reviews)
"Great would definitely stay again "
Zach C.
The price is HK$3,452
HK$4,009 total
includes taxes & fees
14 Nov - 15 Nov
5. 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"
walter l.
The price is HK$1,287
HK$2,819 total
includes taxes & fees
24 Nov - 25 Nov
6. Grand Marina Suite by Brightwild Waterfront
Grand Marina Suite by Brightwild WaterfrontStock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
Pawel
The price is HK$3,055
HK$5,343 total
includes taxes & fees
15 Nov - 16 Nov
7. 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"
Jennifer
The price is HK$1,245
HK$3,845 total
includes taxes & fees
18 Nov - 19 Nov
8. 43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to DowntownStock Island
10.0 out of 10, Exceptional, (7 reviews)
"We loved staying on this beautiful boat and all the amenities of the Perry Marina. Will definitely stay again: highly recommend "
Erin S.
The price is HK$2,204
HK$3,385 total
includes taxes & fees
23 Nov - 24 Nov
9. 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. "
Teri K.
The price is HK$1,425
HK$3,848 total
includes taxes & fees
16 Nov - 17 Nov
10. 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 WestOld Town Key West
9.8 out of 10, Exceptional, (27 reviews)
"Awesome location & very helpful host!"
Jay M.
The price is HK$974
HK$2,866 total
includes taxes & fees
16 Nov - 17 Nov
11. Poolside Cottage #412
Poolside Cottage #412Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
shannon b.
The price is HK$1,451
HK$2,467 total
includes taxes & fees
1 Dec - 2 Dec
12. 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."
Brett W.
The price is HK$1,434
HK$3,783 total
includes taxes & fees
15 Nov - 16 Nov
13. The Elizabeth Suite | Shared Pool in Old Town
The Elizabeth Suite | Shared Pool in Old TownKey West Historic District
9.6 out of 10, Exceptional, (12 reviews)
"The stay was amazing. The host was available and great to talk to to resolve any issues! Would highly recommend !"
Sheila M.
The price is HK$3,488
HK$5,374 total
includes taxes & fees
14 Nov - 15 Nov
14. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Salvador's Seclusion | Cozy Studio Retreat w/ Heated PoolOld 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."
Shawn
The price is HK$884
HK$2,650 total
includes taxes & fees
17 Nov - 18 Nov
15. The Salt Cay | Updated! Stunning Sunset View, Pool
The Salt Cay | Updated! Stunning Sunset View, PoolKey West
9.6 out of 10, Exceptional, (60 reviews)
"Good place to stay away from the crowds in Old Town. About a 15-20 minute golf cart ride into Old Town - very convenient! Unit was clean and had everything we needed. Beds and pillows were comfortable!"
Dana P.
The price is HK$1,425
HK$3,816 total
includes taxes & fees
15 Nov - 16 Nov
16. Sea Esta Suite | Located On Iconic Duval w/ Pool
Sea Esta Suite | Located On Iconic Duval w/ PoolOld Town Key West
9.6 out of 10, Exceptional, (59 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
Rick H.
The price is HK$1,525
HK$5,685 total
includes taxes & fees
16 Nov - 17 Nov
17. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!Old Town Key West
10.0 out of 10, Exceptional, (15 reviews)
"Wonderful stay, location was great!"
Taffy M.
The price is HK$1,561
HK$3,063 total
includes taxes & fees
2 Dec - 3 Dec
18. Lighthouse Suites Collection
Lighthouse Suites CollectionOld Town Key West
10.0 out of 10, Exceptional, (2 reviews)
"My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable."
Melissa
The price is HK$4,738
HK$6,664 total
includes taxes & fees
19 Nov - 20 Nov
19. Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
Duval Hideaway | Dog-Friendly w/ Shared Hot TubOld 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."
Jenn O.
The price is HK$1,254
HK$3,856 total
includes taxes & fees
6 Dec - 7 Dec
20. 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, (28 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."
EMIN
The price is HK$1,254
HK$3,480 total
includes taxes & fees
24 Nov - 25 Nov
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
The Southernmost Inn - Adults Only
10/10 Excellent
Find out more about Fleming Key
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