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Compare 632 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, (34)
"Great place in a very convenient location! Pull out couch isn’t the most comfortable thing in the world, but it sleeps. Super clean, super easy check in (was even able to get in early) and a great price! "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Spec. Jan 26-31 --219. lodg + 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. Jan 26-31 --219. lodg + w. 3 night stay close beach

Poolside Cottage #411

10.0 out of 10, Exceptional, (37)
"From the moment we stepped on the property it was a great experience. We were pleasantly surprised to have a small water view from the front deck of the condo. Walking/biking trail was accessible right outside the property and we could easily walk to a public beach from the property. The condo was well stocked and we had everything we needed to cook our own meals. The resort was quiet and extremely clean. Only disappointment was that “Gumbos” the small bar on property has been closed. Will...
The price is AED 1,241
AED 1,923 total
includes taxes & fees
12 Feb - 13 Feb
Poolside Cottage #411

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

9.6 out of 10, Exceptional, (31)
"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, (208)
"We always stay at this location when available. There’s another one at the rear of the property and it was a good spot but we’re spoiled by this one. We’ve stayed here so much it is almost like a second home. It’s well appointed, the shower is huge and the place is cozy and has the lived in feel to it. There’s plenty of basics in the kitchen, full size fridge and stove, the bed is outstanding and adjustable, and there’s even beach chairs to use while staying. Marilyn is a great host and super...
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, (175)
"My family enjoyed our stay at Captain’s Quarters. The children especially enjoyed the heated pool and there was adequate room for the seven of us. The bedding was comfortable and it was handy that all of the bedrooms had TVs. There is normally places to park out front if one happens to have a golf cart. There are some issues that need to be addressed and we had many electrical plugs that were very old and wouldn’t work so charging phones became an issue. … It could use a freshen up as window...
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, (54)
"Amazing time and experience! "
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, (3)
"Had a wonderful short trip to the keys - this place was in the perfect location to walk all of Key West from shopping Duval street shopping and sight seeing ate lighthouse and even the coast guard station - would highly recommend. "
The price is AED 1,613
AED 3,614 total
includes taxes & fees
4 Feb - 5 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, (88)
"Beautiful property. Great communication. Very clean. Literally right next to duval street. Highly recommend "
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, (25)
"Great property! Easy to get back and forth to Key West! Loved the water view!"
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 4,489
AED 8,038 total
includes taxes & fees
13 Feb - 14 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"
The price is AED 2,810
AED 3,912 total
includes taxes & fees
16 Feb - 17 Feb
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, (63)
"Except for the very uncomfortable couch we had a nice stay."
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!

Gone Coastal

9.8 out of 10, Exceptional, (9)
"Love the stay everything was amazing "
Gone Coastal

Poolside Cottage #412

9.8 out of 10, Exceptional, (16)
"We really enjoyed this property as a mid vacation stop. We did 2 nights in Key Largo, 4 nights here, and 3 nights in Miami. We were thrilled to have the full kitchen, included parking space, and the laundry was free (I was almost expecting it to be coin operated). This unit is one I would 100% stay at again. My only complaints were we found the bed in bedroom to be warm (mattress cover was thick so we actually utilized Murphy bed in living room more). The ceiling fan in bedroom is also very...
The price is AED 1,241
AED 1,923 total
includes taxes & fees
2 Feb - 3 Feb
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

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2250)
"The staff were lovely and the service was excellent. Looking forward to a return visit this spring "
The price is AED 1,650
AED 2,104 total
includes taxes & fees
3 Feb - 4 Feb
Southernmost Beach Resort

Margaritaville Beach House Key West

4.0 star property
8.6 out of 10, Excellent, (1746)
"Excellent resort with easy access to beach across the road definitely a place for all to stay "
The price is AED 1,392
AED 1,805 total
includes taxes & fees
2 Feb - 3 Feb
Margaritaville Beach House Key West

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1008)
"Very nice."
The price is AED 933
AED 1,267 total
includes taxes & fees
2 Feb - 3 Feb
The Perry Hotel & Marina Key West
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.