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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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!
Exterior detail

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!
A heated pool

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
Terrace/patio

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
Exterior detail

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!
Terrace/patio

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

8.8 out of 10, Excellent, (47)
"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
A heated pool

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!
A heated pool

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

9.6 out of 10, Exceptional, (77)
"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!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (181)
"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
A heated pool

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 1,587
AED 3,823 total
includes taxes & fees
16 May - 17 May
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
A heated pool

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!
A heated pool

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!
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!

9.8 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!
Outdoor pool, a heated pool

Perfect Location, Private Heated Pool & Pristine Luxury Home!

10.0 out of 10, Exceptional, (172)
"Location was great and we had an amazing weekend!"
The price is AED 3,673
AED 7,163 total
includes taxes & fees
11 May - 12 May
Perfect Location, Private Heated Pool & Pristine Luxury Home!
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
A heated pool

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

9.8 out of 10, Exceptional, (84)
"Beautiful property. Short walk to Duval"
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
Outdoor dining

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…
Beach

**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
Beach towels

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 1,084
AED 2,623 total
includes taxes & fees
9 Jun - 10 Jun
Luxury two floor apartment in prime location of famous Duval Street
Poolside Cottage #412
Outdoor dining

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
A heated pool

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 2,390
AED 5,442 total
includes taxes & fees
16 May - 17 May
Conch Cove - 3br/3ba with private heated pool and private parking
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
A heated pool

Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool

8.8 out of 10, Excellent, (38)
"A great location and very charming"
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w 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
9.0 out of 10, Wonderful, (137)
"Would definitely stay here again! "
The price is AED 505
AED 1,184 total
includes taxes & fees
21 May - 22 May
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool

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!
Beach towels

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.