Fleming Key Vacation Rentals

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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Browse Select Fleming Key Vacation Homes

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, (192)
"This home is great location , fits party of up to 6 perfectly "
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)
"We had a wonderful stay. The house was perfect. Plenty of privacy yet we were steps away from all that duval st has to offer. Super clean, super nice, perfect for our family. Highly recommend!"
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes
Terrace/patio

NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes

9.0 out of 10, Wonderful, (161)
"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!"
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen
Exterior detail

Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen

9.6 out of 10, Exceptional, (215)
"We enjoyed our stay very much. The time went too quickly. Communication with the host was excellent. The weather was beautiful and the place was cosy. "
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds

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

8.8 out of 10, Excellent, (45)
"We just needed a place for a couple of nights so that we could make the day trip to Dry Tortugas NP. This fit the bill! It wasn’t fancy but we felt safe and were easily able to fit our family of 5. But I wouldn’t have stayed for longer than 2 nights as we would’ve been cramped. We had everything we needed and all the necessary instructions ahead of time. And the view off of the back deck was pretty incredible! Also, if you don’t have a sound machine, be prepared for a rooster alarm clock!"
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, (126)
"We've stayed at this property 3 times and we love it. Prefect size. Great communication "
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, (75)
"Perfect house with a great pool and amazing location to Duval and grocery store across the street. Highly recommend."
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, (180)
"Very nice home. Great location. Thanks for sharing."
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, (18)
"The property was as described. The location was perfect and quiet. We'd love to the pool and hanging out there. Customer service was outstanding."
The price is CA $392
CA $1,074 total
includes taxes & fees
Apr 29 - Apr 30
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)
"Just the right set up for our multigenerational family Spring Break. The management company was extremely helpful and accommodating. We highly recommend. "
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, (182)
"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
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (14)
"We loved our location, the house and Key West!"
The price is CA $896
CA $1,714 total
includes taxes & fees
May 26 - May 27
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - 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!

9.8 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!
Outdoor pool, a heated pool

Perfect Location, Private Heated Pool & Pristine Luxury Home!

10.0 out of 10, Exceptional, (168)
"This home is fully dialed in. Beautiful finishings, all the towels, sunscreen, and pool accessories you could ask for, and a perfect layout with gorgeous private pool and beautifully landscaped backyard space. Would definitely stay here again!"
The price is CA $1,386
CA $2,715 total
includes taxes & fees
May 13 - May 14
Perfect Location, Private Heated Pool & Pristine Luxury Home!
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
A heated pool

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

9.8 out of 10, Exceptional, (83)
"Great location "
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
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

9.8 out of 10, Exceptional, (146)
"This property is amazingly situated and very well appointed. We have stayed here several times, and it does not disappoint in any respect. The convenience of location (and parking) is amazing and cannot be beat. It's enough off the main street to be comfortably quiet, but you can still enjoy the live music at a level which does not impede conversation while outside. Super clean with high end finishes. The private pool is mostly shaded, which is wonderfully refreshing after being out and about."
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (87)
"Our stay at Dockside Daydreams was great and we appreciated the extra thoughtful touches, like the beach towels, chairs, and cooler! Our contact at Last Key Services was attentive and responded quickly to inquiries. I would definitely recommend this property to anyone heading to Key West. "
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Luxury two floor apartment in prime location of famous Duval Street
Property grounds

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (77)
"Great property in a fantastic location. Perfect for getting around to all the must see places. We had a golf cart, and there was even dedicated parking for that. Enjoyed sitting on the outdoor balcony people watching. Host was very responsive to our inquiries. Would definitely book again!"
The price is CA $547
CA $1,177 total
includes taxes & fees
May 5 - May 6
Luxury two floor apartment in prime location of famous Duval Street
Poolside Cottage #412
Outdoor pool

Poolside Cottage #412

9.6 out of 10, Exceptional, (22)
"Nice condo. Great location.Would have preferred a king size bed though."
The price is CA $310
CA $520 total
includes taxes & fees
May 5 - May 6
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, (11)
"Great spot walking 10-15 minutes or less from most places. Property managers were grear"
The price is CA $672
CA $1,645 total
includes taxes & fees
Apr 29 - Apr 30
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
Deluxe Bungalow | Private kitchen

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (131)
"Really enjoyed the stay. All our “neighbors” were respectful of each other The boat house was clean The manatees stole the show!"
The price is CA $148
CA $399 total
includes taxes & fees
Apr 27 - Apr 28
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Terrace/patio

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (293)
"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 $456
CA $552 total
includes taxes & fees
May 4 - May 5
Hyatt Vacation Club at Sunset Harbor, Key West
Coconut Mallory Resort And Marina By Kees Vacations
Meeting facility

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
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.