Fleming Key Holiday Rentals

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Our top choices for Fleming Key holiday 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 AU$556
includes taxes & fees
8 Mar - 9 Mar
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 AU$741
includes taxes & fees
2 Mar - 3 Mar
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 AU$747
includes taxes & fees
23 Mar - 24 Mar
Living the Dream Key West Style

Holiday 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 AU$1,596
includes taxes & fees
25 Feb - 26 Feb
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 AU$1,443
includes taxes & fees
11 Mar - 12 Mar
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 AU$693
includes taxes & fees
18 Mar - 19 Mar
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Holiday 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 Lighthouse - Beach Houses Key West

Holiday 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 AU$2,374
includes taxes & fees
1 Mar - 2 Mar
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 AU$1,003
includes taxes & fees
1 Mar - 2 Mar
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 AU$702
includes taxes & fees
12 Mar - 13 Mar
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 AU$1,315
includes taxes & fees
10 Mar - 11 Mar
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 AU$556
includes taxes & fees
24 Mar - 25 Mar
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 AU$656
includes taxes & fees
25 Mar - 26 Mar
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Holiday 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 AU$2,399
includes taxes & fees
8 Mar - 9 Mar
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 AU$758
includes taxes & fees
22 Mar - 23 Mar
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 AU$692
includes taxes & fees
25 Feb - 26 Feb
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 AU$1,201
includes taxes & fees
3 Mar - 4 Mar
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 AU$928
includes taxes & fees
10 Mar - 11 Mar
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 AU$843
includes taxes & fees
25 Feb - 26 Feb
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 AU$1,001
includes taxes & fees
4 Mar - 5 Mar
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.

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Top Fleming Key Hotel Reviews

Find out more about Fleming Key

Everything you need to know about Fleming Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fleming Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fleming Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fleming Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fleming Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fleming Key holiday rentals we have selected for you start as low as AU$443 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fleming Key rentals

At Expedia, we put the best Fleming Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Fleming Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fleming Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fleming Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.