Fleming Key Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Fleming Key

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (165)
"The stay was beautiful "
United States
Jennifer
$265 nightly
The price is $298
Nov 2 - Nov 3
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very Good, (314)
"Good location "
United States
Paula
$276 nightly
The price is $310
Nov 19 - Nov 20
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (407)
"Great place to stay and walk to all the attractions."
United States
Byron Debi L.
$204 nightly
The price is $227
Nov 16 - Nov 17
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
8.2 out of 10, Very Good, (820)
"Overall a good place to stay and value for money "
United States
Vijay Bhasker
Coconut Mallory Resort And Marina By Kees Vacations
Duval Delight | Recently Remodeled Condo on Duval!
9.8 out of 10, Exceptional, (34)
"We had a wonderful host Rick just helped us out so much with everything thing we enjoyed the condo everything was great could not ask for a better vacation"
United States
Robert W.
$466 nightly
The price is $512
Nov 10 - Nov 11
Total with taxes and fees
Duval Delight | Recently Remodeled Condo on Duval!
Perfect Location, Private Heated Pool, Pristine Luxury Home!
10.0 out of 10, Exceptional, (192)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
$1,587 nightly
The price is $1,762
Nov 4 - Nov 5
Total with taxes and fees
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Island View 1BR Residence With Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
$336 nightly
The price is $378
Nov 4 - Nov 5
Total with taxes and fees
Island View 1BR Residence With Balcony
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
9.2 out of 10, Wonderful, (184)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location in the middle of everything"
United States
Loyd K.
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
8.6 out of 10, Excellent, (139)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
$321 nightly
The price is $357
Nov 2 - Nov 3
Total with taxes and fees
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
6.6 out of 10, (12)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
United States
p j.
$335 nightly
The price is $371
Nov 5 - Nov 6
Total with taxes and fees
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Living the Dream Key West Style
10.0 out of 10, Exceptional, (31)
"Clean rooms pet friendly great view! Exactly as advertised "
United States
Todd
$307 nightly
The price is $341
Nov 11 - Nov 12
Total with taxes and fees
Living the Dream Key West Style
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
9.8 out of 10, Exceptional, (48)
"Wonderful view, lot's of space, great location "
United States
Valerie
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
Heart of Downtown Key West Cottage With Off-Street Parking
10.0 out of 10, Exceptional, (140)
"Wonderful property. Perfect location. Clean building. Everything you needed for a relaxing stay. Lovely hosts as well. Will stay there again. "
United States
Andrew C.
Heart of Downtown Key West Cottage With Off-Street Parking
WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool
9.6 out of 10, Exceptional, (14)
"We had a fantastic stay at The Inn on Fleming! The location is ideal—quiet enough to relax, yet just a short bike ride to Duval Street and all the Key West action. The inn itself is charming, well-maintained, and has a lovely historic feel with modern amenities.Our room was clean, cozy, and tastefully decorated, with a comfortable bed and great air conditioning (a must in Key West!). Highly recommend The Inn on Fleming for couples or families looking for a relaxing and authentic Key West...
United States
Jessica C.
$223 nightly
The price is $247
Nov 11 - Nov 12
Total with taxes and fees
WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool
Super-Cozy boat in Key West!
$277 nightly
The price is $308
Nov 2 - Nov 3
Total with taxes and fees
Super-Cozy boat in Key West!
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
10.0 out of 10, Exceptional, (23)
"Great location and getaway. Steps away from Duval street and restaurants. Highly recommend!"
United States
Alex J.
$341 nightly
The price is $376
Nov 30 - Dec 1
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
10.0 out of 10, Exceptional, (24)
"11/10 stay and service, Marie was so amazing and allowed for early check in and late check out for my birthday weekend. Location was so perfect and had golf cart rental next door. Will definitely be staying here next time I come to the keys! "
United States
Julie G.
$343 nightly
The price is $378
Nov 16 - Nov 17
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
9.2 out of 10, Wonderful, (98)
"These were very quaint cottages and a fantastic location close to everything you’d want to see and experience"
United States
Kevin M.
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
9.8 out of 10, Exceptional, (24)
"Great location. Close to everything but very quiet. Easy access and the property manager was super helpful with parking and accommodations. Would stay here again 100%!"
United States
Katie B.
$344 nightly
The price is $379
Nov 18 - Nov 19
Total with taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!
9.8 out of 10, Exceptional, (141)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful location, clean, cozy and very private. I will definitely return.."
United States
Teresa K.
$211 nightly
The price is $234
Nov 4 - Nov 5
Total with taxes and fees
FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Fleming Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Fleming Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $227 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Fleming Key rentals

At Expedia, we put the best Fleming Key vacation 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 vacation.

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.