Fleming Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Fleming Key vacation rentals

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
9.0 out of 10, Wonderful, (180 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is CA $277
CA $542 total
includes taxes & fees
Mar 8 - Mar 9
Aqua Lodges at Hurricane Hole Marina
7.8 out of 10, Good, (29 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is CA $360
CA $717 total
includes taxes & fees
Mar 3 - Mar 4
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Houseboat in Stock Island

Living the Dream Key West Style
9.8 out of 10, Exceptional, (47 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is CA $575
CA $729 total
includes taxes & fees
Mar 9 - Mar 10
Living the Dream Key West Style

Vacation Home in Upper Sugarloaf Key

Private and Exclusive Florida Keys Getaway
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is CA $746
CA $1,585 total
includes taxes & fees
Feb 25 - Feb 26
Private and Exclusive Florida Keys Getaway
8.6 out of 10, Excellent, (140 reviews)
"Beautiful property! Pool was phenomenal. There is a men’s and a Womens sauna separately. The common area greenery is beautiful. Thank you"
United States
Amanda G.
The price is CA $634
CA $1,408 total
includes taxes & fees
Mar 11 - Mar 12
Comfortable Condo with Pool, Private Balcony, & Beach Access
9.8 out of 10, Exceptional, (120 reviews)
"we had a wonderful room with a great location. It was too cold to use the pool, but it looked very inviting. Would definitely stay again."
United States
Richard
The price is CA $376
CA $683 total
includes taxes & fees
Mar 18 - Mar 19
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Vacation Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is CA $1,657
CA $2,817 total
includes taxes & fees
Mar 12 - Mar 13
The Lighthouse - Beach Houses Key West

Vacation Home in Raccoon Key

Capmar House at Lunara Bay
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is CA $1,094
CA $2,337 total
includes taxes & fees
Mar 1 - Mar 2
Capmar House at Lunara Bay
9.6 out of 10, Exceptional, (31 reviews)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
The price is CA $685
CA $981 total
includes taxes & fees
Mar 1 - Mar 2
Grand Marina Suite - Poolside & Waterfront Condo
8.8 out of 10, Excellent, (120 reviews)
"We all had a great time and the place was very clean! "
United States
Rebekah A.
The price is CA $305
CA $689 total
includes taxes & fees
Mar 12 - Mar 13
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is CA $818
CA $1,275 total
includes taxes & fees
Mar 1 - Mar 2
Grand Marina Suite by Brightwild Waterfront

Apartment in Old Town Key West

Bahama Village studio @ the Galleria!
9.4 out of 10, Exceptional, (16 reviews)
"The bedding was comfy and soft! They provided bathroom essentials and coffee which was a nice bonus. Small but exactly as pics showed! We loved our stay, thank you! "
United States
Carrie H.
The price is CA $294
CA $546 total
includes taxes & fees
Mar 24 - Mar 25
Bahama Village studio @ the Galleria!
8.8 out of 10, Excellent, (210 reviews)
"Good stay, everything was comfortable and ready to check in along with the typical amenities you would see at traditional hotels. Only stayed one night but there was a strong odor in the apartment, may have been from previous guests’ cooking but wasn’t unpleasant. Would stay again. "
United States
Juan E.
The price is CA $274
CA $645 total
includes taxes & fees
Mar 25 - Mar 26
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Vacation Home in Raccoon Key

The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (20 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is CA $1,093
CA $2,339 total
includes taxes & fees
Mar 8 - Mar 9
The Seagate Estate at Lunara Bay
9.6 out of 10, Exceptional, (98 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is CA $455
CA $784 total
includes taxes & fees
Mar 22 - Mar 23
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
9.8 out of 10, Exceptional, (23 reviews)
"Really enjoyed our stay. Location was great and the property was well kept."
United States
linda k.
The price is CA $292
CA $670 total
includes taxes & fees
Feb 25 - Feb 26
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
9.8 out of 10, Exceptional, (38 reviews)
"Comfortable condo in a great location. Pet friendly, which is a great plus!"
United States
Chrislyn R.
The price is CA $614
CA $1,187 total
includes taxes & fees
Mar 3 - Mar 4
The Butterfly Nest | Newly Updated w/ Shared Pool
9.0 out of 10, Wonderful, (38 reviews)
"Very enjoyable other than the rooster started crowing at 4:30 AM."
United States
Carol
The price is CA $616
CA $911 total
includes taxes & fees
Mar 18 - Mar 19
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
9.8 out of 10, Exceptional, (40 reviews)
"Great place!!! Private with but still in the middle of everything. 5+ stars will be back in November!!!"
United States
Rob
The price is CA $362
CA $818 total
includes taxes & fees
Feb 25 - Feb 26
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Cottage in Old Town Key West

OSPREY STUDIO @ The Colony-Sleeps up to 4
9.6 out of 10, Exceptional, (55 reviews)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
The price is CA $396
CA $984 total
includes taxes & fees
Mar 4 - Mar 5
OSPREY STUDIO @ The Colony-Sleeps up to 4
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Fleming Key Hotel Reviews

Find out more about Fleming Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Fleming Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.