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Compare 596 Vacation Homes in Fleming Key with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (35)
"Stay was fun and place was clean. Could use a little improvement. Couch was u comfortable and coffeetable broken. The bikes def need some attending to. The table outside is very nice but a little too high; needs adjusting. Hot tub was wonderful and it was quiet for sleeping. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

9.0 out of 10, Wonderful, (157)
"The good: convenient location, quiet, bed was comfortable, the little patio in the back is nice. The bad: there is no “on site’ parking but we always found parking on the street about a block away, The communication with property manager was a bit strange, she accused us of still being inside the unit a full day after we had check out on time, despite texting her to tell her we had left (an hour before check out)"
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is AED 1,242
AED 1,916 total
includes taxes & fees
3 Mar - 4 Mar
Poolside Cottage #411

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

9.4 out of 10, Exceptional, (33)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

9.6 out of 10, Exceptional, (209)
"Had enjoyable three day visit in Key West. Stayed in comfortable little VRBO house apartment in southern part of Old Town. "
Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

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

9.6 out of 10, Exceptional, (176)
"The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We spent 4 days and 3 nights. Captains Quarters was wonderful. Great location with avg transportation cost of 8. Loved the front porch and the neighborhood. Keep in mind there is an early noise ordinances at 8pm so you need to be mindful at the pool if night...
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Villa Déjà vu Key West - Steps Off Duval w Private Pool

9.4 out of 10, Exceptional, (55)
"This house was exactly what our group was looking for. Loved the location and proximity to Duval Street. Also loved the outdoor pool area for hanging out. Would def recommend. "
Villa Déjà vu Key West - Steps Off Duval w Private Pool

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (63)
"This property was awsome! The area is quiet and close to grocery stores. And a.short drive to down townlpve it, love it, love it. Definitely coming back!!"
Coastal Comfort; Waterfront Luxury Home with private pool!

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (4)
"We enjoyed our stay here. The location was great. We even walked the mile to the dock to board the Yankee Freedom III for a trip to the Dry Tortugas.The apartment was comfortable and had plenty of room for the 5 of us adults. We didn’t use the kitchen much, only to make coffee, so we can’t speak to anything in regards to that."
The price is AED 1,283
AED 3,161 total
includes taxes & fees
26 Feb - 27 Feb
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (90)
"Clean, roomy, comfortable. Adequate seating and dishes for 6 adults. Great mattresses and pillows. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

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

9.6 out of 10, Exceptional, (26)
"Very comfortable unit to stay near Key West.Beautiful water view.Just 15-20 min from downtown .Will stay again . "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (25)
"We truly enjoyed our stay at the Flower Power House! The house was awesome, in a great neighborhood and had everything we needed! The property manager was very pleasant, responsive and accommodating! We will definitely return the next time we are in Key West! Thank you! "
The Flower Power House - Boho Beautiful

Conch Cove - 3br/3ba with private heated pool and private parking

10.0 out of 10, Exceptional, (4)
"Rick and team were awesome and exceptional throughout the whole stay! Nice house!! "
The price is AED 3,266
AED 6,362 total
includes taxes & fees
23 Feb - 24 Feb
Conch Cove - 3br/3ba with private heated pool and private parking

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

2.0 star property
6.0 out of 10, (2)
"Plenty of room indoors and outdoors to live in. Comfortable beds. Clean and tidy"
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (200)
"Delighted with the location & size. Quiet but close to activities. Enjoyed the outdoor space- well appointed."
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

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

9.6 out of 10, Exceptional, (65)
"Overall the best things about the home was location to Duval St and historic sites. The pool was relaxing and the large covered porch with big table was an ideal place to eat and hang outdoors."
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!

9.8 out of 10, Exceptional, (64)
"Key West is very walkable and the Blue Bungalow is a great place to start - Truman Waterfront Park and Zachary Taylor State Park in one direction, The Green Parrot and Duval Street in the other. Whitney was a great host - very responsive. Well furnished property. Cleanliness was outstanding. Just a wonderful place to experience paradise!"
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!

Gone Coastal

9.8 out of 10, Exceptional, (10)
"Love the stay everything was amazing "
Gone Coastal

Poolside Cottage #412

9.6 out of 10, Exceptional, (18)
"I recommend this cute little place. Reasonable price,quite and great location. Stayed for 2 weeks, it was like home. Loved it. Thank you"
The price is AED 1,242
AED 1,894 total
includes taxes & fees
11 Mar - 12 Mar
Poolside Cottage #412

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

9.8 out of 10, Exceptional, (77)
"Would return"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated 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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Other property types in Fleming Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (116)
"Great houseboat to stay at. Nice accomidations , something different then your normal hotel room."
The price is AED 1,016
AED 1,660 total
includes taxes & fees
23 Feb - 24 Feb
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (289)
"I had a great experience with my family!"
The price is AED 1,469
AED 1,756 total
includes taxes & fees
26 Feb - 27 Feb
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (803)
"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."
Coconut Mallory Resort And Marina By Kees Vacations
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.