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Compare 644 Vacation Homes in Fleming Key with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (1)
"Rick and his staff made our girl’s trip worry free. Always available for questions and recommendations. Condo was large, beds comfortable, kitchen well stocked and of course located right on Duval. . As we sit here waiting to leave, other than the roosters, we have no negative comments "
The price is ￥92,567
￥186,627 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

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

9.0 out of 10, Wonderful, (31)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (171)
"Accommodations were great. Loft bedroom was a little noisy if people got up early. Noise came straight upstairs. Otherwise accommodations were great. Kitchen well stocked and washer and dryer!! "
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

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

9.6 out of 10, Exceptional, (30)
"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!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool

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

9.6 out of 10, Exceptional, (75)
"This was our first time staying in an air b&b. We absolutely loved our stay! We wish we would have booked for longer. We highly recommend this place as it was super clean, spacious, and relaxing! We will be back! "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Conch Cove - 3br/3ba with private heated pool and private parking
A heated pool

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

10.0 out of 10, Exceptional, (1)
"Property had a wonderful heated pool which was lovely since we had a chilly day. It also provides a lot of shade for when it is really hot out. The location was perfect for walking to everything we wanted to see. Rick, the manger was awesome and was there for anything we needed, would recommend this property to anyone seeking to have a holiday in Key West."
The price is ￥153,059
￥290,012 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Conch Cove - 3br/3ba with private heated pool and private parking
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Beach

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

10.0 out of 10, Exceptional, (185)
"Another fabulous stay at the Lost Shaker of Salt. Great location on Key West. Accommodations met our needs. The pool is delightful. Can’t wait to stay here again when we come back to Key West. "
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
A heated pool

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

9.8 out of 10, Exceptional, (87)
"Loved the house it was awesome for our group plenty of space for our large group. The beds were very comfortable and every thing was clean and looked new. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Terrace/patio

~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

9.8 out of 10, Exceptional, (162)
"Loved this light filled little cottage with a huge back porch and yard. It was a great launching pad for our visit to the area. "
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is ￥52,833
￥81,849 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Poolside Cottage #411
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
A heated pool

Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (98)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
A heated pool

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

9.8 out of 10, Exceptional, (110)
"Ok location. 10 minutes to key west. Nice pool"
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Pool & Parking, Near Duval - Poolside Paradise
Pool

Pool & Parking, Near Duval - Poolside Paradise

9.2 out of 10, Wonderful, (11)
"Great location 1/2 block from Duval. Lots of great towels, and pillows! I didn’t know this is two units connected but no connecting door, you access back unit via the pool. We needed both sofa beds but one had broken springs and was unusable. The floors hadn’t been mopped and all of my kids had black feet from walking around barefoot. If you are planning to cook you might want to bring a decent frying pan and a sharp knife. They have plenty of knives but none sharp. The grill didn’t work and...
The price is ￥131,144
￥240,523 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Pool & Parking, Near Duval - Poolside Paradise
Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch
Exterior detail

Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch

9.6 out of 10, Exceptional, (204)
"Cute, older place in good location, with nice front porch. You can walk, but we rented bikes, and glad we did. Because you have to park on street and only in designated areas, it's hard to find a spot. Place did not seem that clean. Floors were really dirty. Walked 10 steps after getting out of shower and our feet were black!"
Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch
Poolside Cottage #412
Outdoor dining

Poolside Cottage #412

9.8 out of 10, Exceptional, (16)
"Quiet area of the key west neighbors quiet, nice bike ride to key west and grocery store was close by. Would recommend renting from the resort"
The price is ￥52,833
￥81,380 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Poolside Cottage #412
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
Outdoor pool, a heated pool

NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

9.6 out of 10, Exceptional, (196)
"Exactly as advertised with an incredible host. We had a great time in Key West! "
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
A heated pool

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

9.8 out of 10, Exceptional, (171)
"Beautiful, well appointed home in a great neighborhood. Great communication and lovely experience!"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
A heated pool

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

9.6 out of 10, Exceptional, (173)
"Captains Quarters is a beautiful house, great location, walking distance to Duval, clean, heated pool and plenty of amenities to make your stay enjoyable. Would def stay there again. "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio

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

9.8 out of 10, Exceptional, (22)
"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!
A heated pool

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

9.8 out of 10, Exceptional, (204)
"The property looks like the pictures . It is very cozy . It is located in a very quiet neighborhood , about 20 min walking from the center. It does not have a designated parking spot but parking around the house is not a problem. Check in and communication with the property manager is very easy . I read I’m another review that the pool was not warm enough but in our case since we arrived the pool was perfectly warm"
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail 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
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (106)
"Nice for affordable price "
The price is ￥30,606
￥56,413 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (358)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is ￥24,853
￥49,414 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Steps from Duval, Pool on Site & Bikes Included!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is ￥52,833
￥81,849 total
includes taxes & fees
Jan 8 - Jan 9, 2025
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.