Holiday Rentals in Fleming Key

  • 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 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, (175 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is €365
includes taxes & fees
1 Mar - 2 Mar
Aqua Lodges at Hurricane Hole Marina

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, (419 reviews)
"Everything was excellent!"
United States
Susan L.
The price is €366
includes taxes & fees
4 Mar - 5 Mar
Steps from Duval, Pool on Site & Bikes Included!

Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is €628
includes taxes & fees
8 Feb - 9 Feb
Resort View 1BR Suite

Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Place is perfect"
United States
Ryan S.
The price is €376
includes taxes & fees
2 Mar - 3 Mar
Balcony, Pool, & Near Duval - Curry House Room 8

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, (143 reviews)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is €417
includes taxes & fees
4 Mar - 5 Mar
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

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, (118 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 €551
includes taxes & fees
25 Feb - 26 Feb
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (118 reviews)
"Brilliant location… very generous to leave bikes and chairs which was used every day. Well decorated and equipped room and comfy bed . Shower is hot and has great water pressure . Check in and out is easy . Thank you "
United Kingdom
Simon
The price is €400
includes taxes & fees
10 Feb - 11 Feb
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

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

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
8.0 out of 10, Very good, (28 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 €432
includes taxes & fees
9 Feb - 10 Feb
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (41 reviews)
"Perfect, just perfect!"
United States
Mikael
The price is €550
includes taxes & fees
7 Mar - 8 Mar
Living the Dream Key West Style

The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (40 reviews)
"Everything was great."
United States
Keith
The price is €755
includes taxes & fees
8 Feb - 9 Feb
The Salt Cay | Updated! Stunning Sunset View, Pool

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West
Stock Island
The price is €405
includes taxes & fees
12 Feb - 13 Feb
3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

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

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (97 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is €398
includes taxes & fees
9 Feb - 10 Feb
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (2 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is €591
includes taxes & fees
8 Feb - 9 Feb
Island View 1BR Residence With Balcony

Dog-friendly suite with pool, hot tub, tennis & full kitchen

Dog-friendly suite with pool, hot tub, tennis & full kitchen
Key West
8.6 out of 10, Excellent, (122 reviews)
"We like this place, It was clean and quiet"
United States
Julie P.
The price is €591
includes taxes & fees
8 Feb - 9 Feb
Dog-friendly suite with pool, hot tub, tennis & full kitchen

Great Family Vacation Rental.

Great Family Vacation Rental.
Stock Island
8.8 out of 10, Excellent, (15 reviews)
"Enjoyed staying here super clean and well stocked!"
Canada
Kirsty E.
The price is €746
includes taxes & fees
19 Feb - 20 Feb
Great Family Vacation Rental.

Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (24 reviews)
"Loved it can’t wait to book it again!!"
United States
Amanda C.
The price is €469
includes taxes & fees
9 Feb - 10 Feb
Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.6 out of 10, Exceptional, (120 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool
Old Town Key West
9.2 out of 10, Wonderful, (25 reviews)
"Amenities, host, then location"
United States
Tom T.
The price is €455
includes taxes & fees
8 Feb - 9 Feb
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (104 reviews)
"Fabulous view to watch the sunset and planes take off! Super comfortable stay with all the typical amenities and plenty of space. Quiet location close enough to drive/bike to everything you need without all the bustle. Margaret was an amazing, communicative host. "
United States
Chloe C.
The price is €542
includes taxes & fees
7 Feb - 8 Feb
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Poolside Suite with Direct Pool Access

Poolside Suite with Direct Pool Access
Key West
10.0 out of 10, Exceptional, (2 reviews)
"amazing spot close to everything "
United States
Rosalina
The price is €536
includes taxes & fees
8 Feb - 9 Feb
Poolside Suite with Direct Pool Access
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.
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

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 €270 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.