Fleming Key Holiday Rentals

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Our top choices for Fleming Key holiday rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is NZ$719
includes taxes & fees
5 Jan - 6 Jan 2026
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (323)
"Great location and staff was friendly. The pool area was perfect. "
United States
Deborah
Hyatt Vacation Club at Sunset Harbor, Key West

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (26)
"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 NZ$889
includes taxes & fees
4 Jan - 5 Jan 2026
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
The price is NZ$1,031
includes taxes & fees
5 Jan - 6 Jan 2026
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
The price is NZ$2,732
includes taxes & fees
5 Jan - 6 Jan 2026
The Seagate Estate at Lunara Bay

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is NZ$1,859
includes taxes & fees
11 Jan - 12 Jan 2026
Grand Marina Suite by Brightwild Waterfront

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (37)
"The room was perfect for the two of us. The property was clean, and well maintained. Very quiet and lots of privacy. The location was great. Duval Street was within a couple minute walking distance. We will definitely be back!"
United States
Nicole P.
The price is NZ$860
includes taxes & fees
3 Jan - 4 Jan 2026
VanGogh Studio | Updated, Old Town, Heated Pool

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Key West
8.8 out of 10, Excellent, (205)
"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 NZ$714
includes taxes & fees
11 Jan - 12 Jan 2026
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise

Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
Beachside
9.2 out of 10, Wonderful, (142)
"Really nice location and a beautiful pool. The gym/activities area was not well equipped "
United States
Jennifer H.
The price is NZ$3,192
includes taxes & fees
31 Dec - 1 Jan 2026
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise

Palm - Beach Houses Key West

Palm - Beach Houses Key West
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
The price is NZ$3,482
includes taxes & fees
4 Jan - 5 Jan 2026
Palm - Beach Houses Key West

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29)
"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 NZ$2,732
includes taxes & fees
5 Jan - 6 Jan 2026
Capmar House at Lunara Bay

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony & Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony & Pool!
Key West
10.0 out of 10, Exceptional, (24)
"This property is beautiful and the location is great as well. We will be back!"
United States
Patricia K.
The price is NZ$1,137
includes taxes & fees
24 Dec - 25 Dec
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony & Pool!

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (414)
"We loved it here! Not very far from Duval street. "
United States
Keghan J.
The price is NZ$650
includes taxes & fees
3 Jan - 4 Jan 2026
Steps from Duval, Pool on Site & Bikes Included!

Andy’s Attic | Budget-Friendly!

Andy’s Attic | Budget-Friendly!
Old Town Key West
8.2 out of 10, Very good, (26)
"great location"
United States
Carol
The price is NZ$694
includes taxes & fees
24 Dec - 25 Dec
Andy’s Attic | Budget-Friendly!

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is NZ$2,644
includes taxes & fees
5 Jan - 6 Jan 2026
Springtide House at Lunara Bay

SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (110)
"Great value stay"
United States
Mike B.
The price is NZ$902
includes taxes & fees
20 Jan - 21 Jan 2026
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

The Salt Cay | Updated! Stunning Sunset View, Pool!

The Salt Cay | Updated! Stunning Sunset View, Pool!
Key West
9.8 out of 10, Exceptional, (36)
"Everything was great."
United States
Keith
The price is NZ$1,361
includes taxes & fees
5 Jan - 6 Jan 2026
The Salt Cay | Updated! Stunning Sunset View, Pool!

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
Meadows
9.8 out of 10, Exceptional, (38)
"The condo was nicely cleaned and decorated. Love the huge balcony overlooking the water. "
United States
Trysh W.
The price is NZ$1,517
includes taxes & fees
14 Jan - 15 Jan 2026
Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (141)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!
Old Town Key West
9.8 out of 10, Exceptional, (25)
"Awesome location with excellent communication. "
United States
Gary W.
The price is NZ$1,310
includes taxes & fees
9 Jan - 10 Jan 2026
Kingfish Keep | Lively Escape on Duval! Balcony!
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 favorite 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 depends 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 NZ$650 per night. Entering your travel dates in the search wizard you might find 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.