Holiday Rentals in Fleming Key

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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
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is €365
includes taxes & fees
5 Jan - 6 Jan 2026
Aqua Lodges at Hurricane Hole Marina

Holiday Home in Upper Sugarloaf Key

Palm - Beach Houses Key West
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 €1,757
includes taxes & fees
4 Jan - 5 Jan 2026
Palm - Beach Houses Key West

Holiday Home in Raccoon Key

Mirador House at Lunara Bay
9.6 out of 10, Exceptional, (33)
"House was very clean and exactly as shown on the listing. Our group was 15 and it was perfect. The only issue was there were no griddles or pans for the stove/oven. Only pots were provided. We requested pans and they brought them to us. "
United States
Alex M.
The price is €1,870
includes taxes & fees
5 Jan - 6 Jan 2026
Mirador House at Lunara Bay
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 €449
includes taxes & fees
4 Jan - 5 Jan 2026
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Holiday Home in Raccoon Key

The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
The price is €1,387
includes taxes & fees
4 Jan - 5 Jan 2026
The Seagate Estate at Lunara Bay

Holiday Home in Raccoon Key

Waterfront Luxury Home - Tidelands House
2.0 star property
The price is €2,437
includes taxes & fees
7 Jan - 8 Jan 2026
Waterfront Luxury Home - Tidelands House

Holiday Home in Raccoon Key

Springtide House at Lunara Bay
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is €1,333
includes taxes & fees
4 Jan - 5 Jan 2026
Springtide House at Lunara Bay

Houseboat in Stock Island

Living the Dream Key West Style
9.8 out of 10, Exceptional, (36)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
The price is €464
includes taxes & fees
22 Jan - 23 Jan 2026
Living the Dream Key West Style

Holiday Home in Raccoon Key

Larkshine House at Lunara Bay
2.0 star property
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
The price is €2,153
includes taxes & fees
4 Jan - 5 Jan 2026
Larkshine House at Lunara Bay
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 €353
includes taxes & fees
11 Jan - 12 Jan 2026
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
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 €1,604
includes taxes & fees
31 Dec - 1 Jan 2026
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise

Holiday Home in Raccoon Key

Floralee House at Lunara Bay
2.0 star property
9.8 out of 10, Exceptional, (7)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
The price is €1,823
includes taxes & fees
4 Jan - 5 Jan 2026
Floralee House at Lunara Bay

Holiday Home in Raccoon Key

Catchlight House at Lunara Bay
2.0 star property
9.8 out of 10, Exceptional, (6)
"Awesome place definitely recommend if going to key west "
United States
Brandon M.
The price is €2,859
includes taxes & fees
18 Jan - 19 Jan 2026
Catchlight House at Lunara Bay

Holiday Home in Raccoon Key

Suncoast House at Lunara Bay
9.6 out of 10, Exceptional, (41)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is €1,870
includes taxes & fees
4 Jan - 5 Jan 2026
Suncoast House at Lunara Bay
9.8 out of 10, Exceptional, (27)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
The price is €1,380
includes taxes & fees
5 Jan - 6 Jan 2026
Evershore Estate at Lunara Bay | Wellness Home
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is €799
includes taxes & fees
7 Jan - 8 Jan 2026
Grand Marina Suite by Brightwild Waterfront
9.6 out of 10, Exceptional, (414)
"We loved it here! Not very far from Duval street. "
United States
Keghan J.
The price is €328
includes taxes & fees
3 Jan - 4 Jan 2026
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (29)
"2nd time staying here. Love the location and the facilities. Perfect for boating and fishing. The marina is next door so its very convenient. Good times"
United States
robert s.
The price is €545
includes taxes & fees
5 Jan - 6 Jan 2026
Grand Marina Suite - Poolside & Waterfront Condo

Holiday Home in Raccoon Key

Spindrift House at Lunara Bay
10.0 out of 10, Exceptional, (29)
"The BrightWild team is very professional and responsive. Always a great stay every year!"
United States
Chris S.
The price is €1,380
includes taxes & fees
6 Jan - 7 Jan 2026
Spindrift House at Lunara Bay
9.0 out of 10, Wonderful, (179)
"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! "
United States
ALISHA
The price is €448
includes taxes & fees
16 Jan - 17 Jan 2026
Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays
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, apart-hotels, 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 €328 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.