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Compare 640 Vacation Homes in Fleming Key with updated reviews, rates, and availability.

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, (28)
"Location was good. No major complaints. Backyard was really nice. We would stay here again."
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
A heated pool
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
9.8 out of 10, Exceptional, (58)
"Great stay minus the 5am rooster wake up calls! :) Overall a great place in an amazing location. "
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
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, (74)
"I would try this again "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Interior
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!
Terrace/patio
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
9.0 out of 10, Wonderful, (29)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Fridge, microwave, oven, stovetop
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 ￥91,362
￥220,964 total
includes taxes & fees
Nov 17 - Nov 18
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Fridge, microwave, oven, stovetop
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 ￥50,952
￥111,429 total
includes taxes & fees
Nov 24 - Nov 25
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (27)
"Nice STAY"
The price is ￥26,800
￥48,328 total
includes taxes & fees
Nov 18 - Nov 19
Poolside Cottage #411
Poolside Cottage #412
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (13)
"Nice place right by the pool."
The price is ￥26,800
￥48,328 total
includes taxes & fees
Nov 18 - Nov 19
Poolside Cottage #412
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
9.6 out of 10, Exceptional, (19)
"Absolutely stunning view. You can watch so many fish and other sea creatures just swimming by. Anything from Nurse Sharks to Parrot Fish. Even little Horse Shoe Crabs and blue crabs wonder by. The house is adorable and very cozy. It was perfect for coming home after a long day of fishing and exploring. And the hot tub was so wonderful. If you're looking for a little home by the water, I highly recommend this place. We will definitely come back again."
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, (200)
"Enjoyed out stay at this beautiful property. I would definitely recommend to others. "
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
Fridge, microwave, coffee/tea maker, toaster
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 ￥38,220
￥91,836 total
includes taxes & fees
Nov 18 - Nov 19
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
Terrace/patio
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
9.0 out of 10, Wonderful, (150)
"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!
Fridge, microwave, oven, stovetop
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
9.8 out of 10, Exceptional, (168)
"Lively house accommodating the 6 of us very well, with a cozy pool in the backyard. Speedy response for any questions. Clean, comfortable and within a short walk of the Duval St. attractions."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
Exterior detail
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
9.6 out of 10, Exceptional, (198)
"We always love our stay at this location. Marilyn is a wonderful host and treats her return visitors very well. The place is located just a few blocks from anything you want to do in Key West, very cute and comfortable place, and meets our needs perfectly. We love the friendliness of the neighbors and the home is very well maintained. "
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Property grounds
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
Outdoor pool
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
9.8 out of 10, Exceptional, (58)
"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 ￥182,724
￥328,066 total
includes taxes & fees
Nov 10 - Nov 11
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!!
A heated pool
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
9.6 out of 10, Exceptional, (168)
"I absolutely loved this property. It was beautiful and impeccably decorated in true Key West fashion. The house is full of beautiful antiques and nautical art. The management team was very communicative and accommodating. The pool was amazing for a midday break because it was so deep and the perfect temperature. This house was definitely a splurge for us but we made up for it by cooking at home. The kitchen and the house had everything we needed and a working grill so we were able to have...
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Duval Street Suite in Key West
Outdoor dining
Duval Street Suite in Key West
10.0 out of 10, Exceptional, (30)
"Unit was clean and had everything we needed for a comfortable stay! Location was fantastic and an easy walk to everything on Duval. The porch was so nice! Overall really enjoyed this place and would stay again. "
Duval Street Suite in Key West
Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
Beach nearby, beach towels
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.
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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, (104)
"Nice for affordable price "
The price is ￥19,049
￥42,844 total
includes taxes & fees
Nov 11 - Nov 12
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, (352)
"Great communication with host (Ken). I was worried about parking but it was never an issue. We used Uber in the evenings. The studio was very cute and well stocked. I liked all the extras (pool, bikes, beach gear, free laundry machines) Comfortable bed and quiet during the weekend. I would definitely stay again!"
The price is ￥16,597
￥38,049 total
includes taxes & fees
Dec 2 - Dec 3
Steps from Duval, Pool on Site & Bikes Included!
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (27)
"Nice STAY"
The price is ￥26,800
￥48,328 total
includes taxes & fees
Nov 18 - Nov 19
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.