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Compare 736 Vacation Homes in Fleming Key with updated reviews, rates, and availability.

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (193)
"We had a great time staying here. Would recommend to anyone looking to stay near Duval St. Plenty of space for four people for a long weekend. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

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

9.8 out of 10, Exceptional, (98)
"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!

May Spec 159.+ 5-19-23 & 5-26-29 NEWLY Redone. Not shown in current pics I

9.0 out of 10, Wonderful, (164)
"This unit was perfect! Nice updates and a comfortable space close to everything"
May Spec 159.+ 5-19-23 & 5-26-29 NEWLY Redone. Not shown in current pics I

Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen

9.6 out of 10, Exceptional, (216)
"Great location. The room met our needs. It was clean and comfortable. The owner did a great job of communicating everything we needed to know. Everything was walkable, which we appreciated. "
Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen

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

8.8 out of 10, Excellent, (46)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (127)
"Our stay was absolutely incredible. The condo was bigger than we were expecting so we had plenty of room to spread out and relax. The property management website was super helpful and the customer service was amazing as well! Nothing but good reviews from everyone who stayed there!"
Captain's Daughter: Oversized home for the whole family w/private pool & dock

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

9.6 out of 10, Exceptional, (76)
"Excellent location, clean, roomy, wonderful!"
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

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

9.8 out of 10, Exceptional, (180)
"We had 3 couples and the location was great. The house was very nice. "
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

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

10.0 out of 10, Exceptional, (21)
"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 1,283
AED 3,152 total
includes taxes & fees
21 May - 22 May
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

9.8 out of 10, Exceptional, (217)
"We had so much fun! Location was perfect!"
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

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

9.8 out of 10, Exceptional, (183)
"The house was amazing and Shana took very good care of us during our stay, will definitely plan a return trip! "
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

10.0 out of 10, Exceptional, (16)
"Place was perfect and property management was great. Will definitely try to stay here again."
The price is AED 2,450
AED 4,639 total
includes taxes & fees
26 May - 27 May
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

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

9.8 out of 10, Exceptional, (83)
"We very much enjoyed our stay. Very nice condo and beautiful pool close to Key West and Botanical Gardens which we enjoyed!"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Perfect Location, Private Heated Pool & Pristine Luxury Home!

10.0 out of 10, Exceptional, (172)
"Great place. Great location and everything was perfect "
The price is AED 3,673
AED 7,163 total
includes taxes & fees
9 May - 10 May
Perfect Location, Private Heated Pool & Pristine Luxury Home!

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

9.8 out of 10, Exceptional, (83)
"Beautiful property. Short walk to Duval"
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

9.8 out of 10, Exceptional, (147)
"Had a great time in key west. House was close to everything and comfortable "
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

9.8 out of 10, Exceptional, (88)
"Great House, but tight for 5 adults, not sure how 6 adults would fit"
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (80)
"I recently stayed at this amazing property in Key West, and I can confidently say it exceeded all of our expectations. The location was perfect, and we especially loved spending time on the patio."
The price is AED 1,451
AED 3,084 total
includes taxes & fees
12 May - 13 May
Luxury two floor apartment in prime location of famous Duval Street

Poolside Cottage #412

9.6 out of 10, Exceptional, (22)
"The property and our place was really nice. Would definitely stay again. "
The price is AED 793
AED 1,320 total
includes taxes & fees
2 Jun - 3 Jun
Poolside Cottage #412

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

9.6 out of 10, Exceptional, (14)
"perfect for 3 couples! Pool great bonus with a location in the center of it all. "
The price is AED 2,527
AED 5,382 total
includes taxes & fees
28 May - 29 May
Conch Cove - 3br/3ba with private heated pool and private parking
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
9.0 out of 10, Wonderful, (137)
"Would definitely stay here again! "
The price is AED 526
AED 1,207 total
includes taxes & fees
21 May - 22 May
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, (295)
"We had a nice stay. The property was in a great location."
The price is AED 1,090
AED 1,329 total
includes taxes & fees
7 Jun - 8 Jun
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (383)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is AED 400
AED 907 total
includes taxes & fees
11 May - 12 May
Steps from Duval, Pool on Site & Bikes Included!
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.