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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, (189)
"Great place. Quiet and relaxing yet close to everything Key West!"
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, (91)
"Excellent property and location! Really enjoyed the property!"
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

3-22 to 3-24 195 lodg.+ close beach

9.0 out of 10, Wonderful, (159)
"The place was cute; we had everything we needed and it was convenient to all the fun w/o being too close to all the noise and busyness of Duval St. Loved it!"
3-22 to 3-24 195 lodg.+ close beach

Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

9.6 out of 10, Exceptional, (212)
"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. "
Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

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

9.0 out of 10, Wonderful, (38)
"Close to up and coming restaurants on Stock Islabd. Clean manufactored home among trailers."
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, (122)
"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, (72)
"I could not suggest anything that could have made this place any better (someone to peel grapes and feed them to me?) really ideal on every front location accommodations cleanliness communication all 10!"
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, (176)
"We had a great time - the home is spacious with 2 large beds and a nice loft upstairs. Very comfortable for 2 families. The location can't be beat - close to walk but not on top of Duval so nice and quiet. We had an enormous rental car that parked comfortably right in front! Very happy, thanks!"
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, (10)
"Property was located perfect for seeing old Key west area. Property was clean and well maintained. We would definitely stay there again!"
The price is AED 1,746
AED 3,750 total
includes taxes & fees
7 Apr - 8 Apr
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

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

9.6 out of 10, Exceptional, (210)
"Great location. Can walk to everything. Great that there is a parking space for one medium sized car. Loved Hemingway’s Home tour. "
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, (176)
"Absolutely a gorgeous property and fantastic location. Key West is our favorite place to visit. This house, along with the property manager, made this year's visit the best yet! Thanks for a great birthday and we look forward to booking this property again next year"
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, (12)
"Classy, high quality and upscale place to stay with the whole Key West vibe. Our husbands were high fiving us and telling us we hit it out of the park with our selection. The kitchen had all the right amenities and was easy to cook in. We never used the pool because the front porch is the sitting zone and place you want to hang out at. The tenants above were always gracious and never a bother and we left with new friends. Each bedroom had a huge, built in closet with plenty of hanging or...
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, (81)
"This was the perfect place for our family to stay. It was very clean and great location. We will be back for sure!"
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, (166)
"Beautifully appointed house with every amenity that you could need. The location was great - right in heart of all the Key West fun. The pool area was a great place to hang out and relax too. We really enjoyed the property and had a wonderful time!"
The price is AED 5,510
AED 9,520 total
includes taxes & fees
1 Apr - 2 Apr
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, (77)
"We had a family of four, and it was a great trip. The property was a perfect location to walk everywhere. We loved the house. Unlike other house, it was actually cooler on the top floor compared to the other floors, but it worked out well with the bedrooms upstairs. Great communication with the property, and albeit small, the pool was a nice addition. "
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, (145)
"Great location, lots of room. Really enjoyed our stay."
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, (83)
"Clean quiet place with good access to the area"
**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, (76)
"Excellent location, very clean and tastefully decorated. Easy check in. 4 adults so plenty of room. Bedrooms upstairs, mattresses are not very comfy but for a couple nights its fine. Just watch your head with the sloped ceilings!"
The price is AED 1,451
AED 3,121 total
includes taxes & fees
1 Apr - 2 Apr
Luxury two floor apartment in prime location of famous Duval Street

Poolside Cottage #412

9.6 out of 10, Exceptional, (21)
"The cottage was clean and comfortable. We only stayed one night for a wedding, but we would definitely return to use the pool and chill on the cottage's patio. The kitchen had plenty of pots and pans for my next visit! We ubered easily downtown for the wedding and a few drinks afterward. The property manager responded quickly to any questions before arrival."
The price is AED 1,242
AED 1,901 total
includes taxes & fees
9 Apr - 10 Apr
Poolside Cottage #412

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

10.0 out of 10, Exceptional, (6)
"Great location, clean and loved the heated pool! Rick was so accommodating and he and his staff were so kind! Would stay there again! "
The price is AED 2,936
AED 5,909 total
includes taxes & fees
5 Apr - 6 Apr
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
8.8 out of 10, Excellent, (123)
"Was amazing, unlike any place i've ever stayed"
The price is AED 608
AED 1,300 total
includes taxes & fees
2 Apr - 3 Apr
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, (290)
"I had a great experience with my family!"
The price is AED 1,414
AED 1,694 total
includes taxes & fees
24 Apr - 25 Apr
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (376)
"Beautiful place and weather "
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.