Fleming Key Vacation Rentals

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Browse Select Fleming Key Vacation Homes

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)
"Beautiful home with everything needed for a fun family vacation"
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 fantastic stay- this place felt bigger than it looks and is a great location. Two things to note as you consider: 1- the loft bedroom is truly a loft and can see/hear directly into the kitchen area & 2- the pool is a little square. Perfect for cooling off, but not a “swimming” pool. We loved it and would definitely recommend, especially if you don’t want to rent a car. The location is perfect for renting bikes and exploring the entire Key. "
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)
"Very nice facility & good location."
The price is CA $680
CA $1,461 total
includes taxes & fees
Apr 7 - Apr 8
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 "
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...
The price is CA $1,082
CA $1,969 total
includes taxes & fees
Apr 6 - Apr 7
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 CA $2,147
CA $3,709 total
includes taxes & fees
Apr 1 - Apr 2
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)
"We enjoyed our stay in a quaint unit that was close to all the activities in town but far enough away to have quiet evenings sitting by the marina. Highly recommended!!"
**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 CA $565
CA $1,209 total
includes taxes & fees
Apr 1 - Apr 2
Luxury two floor apartment in prime location of famous Duval Street

Poolside Cottage #412

9.6 out of 10, Exceptional, (21)
"We had a great time at this location. It was clean and private. Very nice pool."
The price is CA $484
CA $741 total
includes taxes & fees
Apr 9 - Apr 10
Poolside Cottage #412

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

10.0 out of 10, Exceptional, (6)
"Fantastic location close to just about everything Duval Street and the surrounding areas have to offer, but a block or so away from the noise. Private pool was great and property was as described. Check-in/out process was easy. We contacted the hosts regarding shuttle service from the airport, luggage storage on our final day, and a skimmer for the pool and they took care of everything for us. Super nice and went above and beyond. The only note I'd share for anyone considering would be that if...
The price is CA $1,144
CA $2,302 total
includes taxes & fees
Apr 5 - Apr 6
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 CA $237
CA $507 total
includes taxes & fees
Apr 2 - Apr 3
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)
"This was an amazing property. Wish we had stayed for more than a night and we're already planning a trip to Key West again just to stay here another time. Very friendly and helpful reception staff. Parking deck is directly across the street. Beautiful pool. Near the water (cruise port), a 5 minute walk to Duval Street, and the Truman Little White House was basically next door. Genuinely cannot say enough good things about this hotel."
The price is CA $551
CA $660 total
includes taxes & fees
Apr 24 - Apr 25
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (807)
"Great property for families. Only downside - if you have a room about be, you can hear everything. So ask for higher rent rates m. Great location, spacious chairs nod and super clean. Loved self cater/clean unit!! "
Coconut Mallory Resort And Marina By Kees Vacations
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.