Search Vacation Homes in Fleming Key

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.6 out of 10, Exceptional, (29)
"Beautiful property, amazing outdoor space on the water, clean and comfortable Given the cleaning fees are 50% of the cost I was little annoyed at how much check out chores are required of the guests. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

9.8 out of 10, Exceptional, (59)
"Excellent location, clean, roomy, wonderful!"
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.6 out of 10, Exceptional, (74)
"My brother and I hadn’t seen each other for quite a while. This place offered us so much comfort and convenience. GREAT place to stay. We will be back. Thank you. "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

9.8 out of 10, Exceptional, (114)
"The cottage was perfect for two couples. Both bedrooms had attached bathrooms. Just a few houses down from Duval Street and a few blocks from the beach."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (30)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL

9.8 out of 10, Exceptional, (10)
"Property was clean with everything we needed, including linens and beach towels. Kitchen was fully equipped. The upstairs was a little too warm at night, but it was in the 90's every day during our stay, so we could understand this. One of the twin beds has a mattress that was very uncomfortable, and needs replaced. We have a vacation rental of our own and we were well pleased with this property. We would recommend! Thank you for the little longer checkout time, as the hurricane changed...
The price is HK$4,670
HK$11,294 total
includes taxes & fees
23 Nov - 24 Nov
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

9.0 out of 10, Wonderful, (183)
"Had a great time. Great location. Doesn’t provide more than one trash bag which was an issue we ran into. "
The price is HK$2,436
HK$5,454 total
includes taxes & fees
24 Nov - 25 Nov
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Poolside Cottage #411

10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is HK$1,751
HK$2,962 total
includes taxes & fees
3 Dec - 4 Dec
Poolside Cottage #411

Poolside Cottage #412

10.0 out of 10, Exceptional, (13)
"Nice place right by the pool."
The price is HK$1,751
HK$2,962 total
includes taxes & fees
3 Dec - 4 Dec
Poolside Cottage #412

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.8 out of 10, Exceptional, (21)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

9.8 out of 10, Exceptional, (201)
"The house was clean and conveniently located. We walked to everything!"
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location

9.0 out of 10, Wonderful, (169)
"My sister and I rented the place for ourselves and our 4 young adult kids (ranging from 18-21), and we had a very nice time. The AC is not really "central", has free-standing units in 2 of the bedrooms that vent outside, but they are well installed and do the trick, if a bit tricky to regulate the temperature correctly initially. The place is a typical Key West bungalow that feels like some shoeboxes were nailed together, and the back yard is even smaller than expected. Location is great, we did...
The price is HK$2,249
HK$5,119 total
includes taxes & fees
24 Nov - 25 Nov
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location

Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach

9.0 out of 10, Wonderful, (152)
"A lovely, typical property located in Old Town area of Key West. Very comfortable stay, quiet ensuring good sleep. Great location and I did everything either by walking or on the bicycle I hired. Excellent communication with host who replied within a couple of hours if not sooner!!"
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (168)
"We enjoyed our stay. The house was very clean and in a convenient location. We would stay again."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (200)
"Very walkable. Cozy comfortable place. Cute and safe neighborhood. Setup well for cooking. AC pumps some good cold air. "
Feb 3-10 $245 off the rates close beach full kitchen & patio

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

9.0 out of 10, Wonderful, (222)
"Nice place ,great ammenties very close to duval street, cuban place right on the corner by it is great "
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

9.8 out of 10, Exceptional, (59)
"Elizabeth’s Secret was a perfect cozy home to celebrate our daughter’s 21st birthday and spend fun/quality time with she and her brother/ his girlfriend. We always rent bikes which gets us around town easily to all of our Key West favorites and continue to explore new spots. The pool was enjoyable morning, noon and night. As well as cooking and grilling the fresh fish we caught Monday on the fishing charter we had booked. Off street parking, coolers to use while kayaking at Lazy Dog, blender...
The price is HK$9,340
HK$16,769 total
includes taxes & fees
7 Dec - 8 Dec
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (169)
"Dead growth in yard created a mess constantly on the pool. Out door furniture shows wear and some are broken. Need throw blankets. Blackout curtains would be appreciated in the bedrooms. Some doors do not latch and/or lock. "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Duval Street Suite in Key West

10.0 out of 10, Exceptional, (32)
"The apartment complex was a great choice! The wrap around porch was the best of all to be able to sit out morning, noon and night and get sun on one side or be in the shade on the other!! The people watching was the best part of all and of course make sure to experience Duval Street. Great food music beaches and music to enjoy!! All with in walking distance! This is one not to miss!! If you choose this home make sure and go by the Asian bistro and tell the manager bartender hi!! She’s one not...
Duval Street Suite in Key West

Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach

10.0 out of 10, Exceptional, (193)
"Great to deal with. Clean and very comfortable! We would definitely stay again! Thank you. "
Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
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.
Don't see what you're looking for?
See all available properties in Fleming Key
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Fleming Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is HK$1,044
HK$2,269 total
includes taxes & fees
5 Dec - 6 Dec
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (356)
"We walked most everywhere and loved the Southernmost Beach Bar! Eating at Moon Dog Cafe was so spectacular that we ate there 3 times in 2 days! This place is all it says it is. Simply perfect. "
The price is HK$1,004
HK$2,143 total
includes taxes & fees
22 Dec - 23 Dec
Steps from Duval, Pool on Site & Bikes Included!

Poolside Cottage #411

10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is HK$1,751
HK$2,962 total
includes taxes & fees
3 Dec - 4 Dec
Poolside Cottage #411
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.