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
Stock Island
8.8 out of 10, Excellent, (165)
"The stay was beautiful "
United States
Jennifer
$277 nightly
The price is $312
Nov 15 - Nov 16
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very Good, (314)
"Good location "
United States
Paula
$263 nightly
The price is $295
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West
9.6 out of 10, Exceptional, (408)
"Great place to stay and walk to all the attractions."
United States
Byron Debi L.
$203 nightly
The price is $226
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
Key West
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

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

Key West
8.6 out of 10, Excellent, (139)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
$333 nightly
The price is $369
Nov 10 - Nov 11
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

Stock Island
6.6 out of 10, (12)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
United States
p j.
$334 nightly
The price is $370
Nov 11 - Nov 12
Total with taxes and fees
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Old Town Key West
10.0 out of 10, Exceptional, (192)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
$1,586 nightly
The price is $1,761
Nov 11 - Nov 12
Total with taxes and fees
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Heart of Downtown Key West Cottage With Off-Street Parking

Key West Historic District
10.0 out of 10, Exceptional, (141)
"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

Wahoo Way | Charming Hideaway On Duval Street!

Old Town Key West
9.0 out of 10, Wonderful, (17)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Easy walks to everything!"
United States
Don N.
$288 nightly
The price is $317
Nov 17 - Nov 18
Total with taxes and fees
Wahoo Way | Charming Hideaway On Duval Street!

Island View 1BR Residence With Balcony

2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
$335 nightly
The price is $377
Nov 12 - Nov 13
Total with taxes and fees
Island View 1BR Residence With Balcony

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Beachside
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!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Old Town Key West
9.2 out of 10, Wonderful, (186)
"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!

Super-Cozy boat in Key West!

Key West
$285 nightly
The price is $316
Nov 10 - Nov 11
Total with taxes and fees
Super-Cozy boat in Key West!

Living the Dream Key West Style

Stock Island
10.0 out of 10, Exceptional, (31)
"Clean rooms pet friendly great view! Exactly as advertised "
United States
Todd
$306 nightly
The price is $340
Nov 11 - Nov 12
Total with taxes and fees
Living the Dream Key West Style

FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

Old Town Key West
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.
$212 nightly
The price is $235
Nov 10 - Nov 11
Total with taxes and fees
FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Old Town Key West
10.0 out of 10, Exceptional, (23)
"Great location and getaway. Steps away from Duval street and restaurants. Highly recommend!"
United States
Alex J.
$339 nightly
The price is $373
Nov 30 - Dec 1
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Kingfish Keep | Lively Escape on Duval! Balcony!

Old Town Key West
9.8 out of 10, Exceptional, (20)
"Awesome location with excellent communication. "
United States
Gary W.
$359 nightly
The price is $395
Nov 16 - Nov 17
Total with taxes and fees
Kingfish Keep | Lively Escape on Duval! Balcony!

Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis

Beachside
9.0 out of 10, Wonderful, (103)
"Everything was even better than in the pictures"
United States
john c.
$605 nightly
The price is $672
Nov 14 - Nov 15
Total with taxes and fees
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis

Duval Delight | Recently Remodeled Condo on Duval!

Old Town Key West
9.8 out of 10, Exceptional, (34)
"Convenient location, clean, and accurate description. Everything we were looking for. Thank you!"
United States
Valerie K.
$463 nightly
The price is $509
Nov 10 - Nov 11
Total with taxes and fees
Duval Delight | Recently Remodeled Condo on Duval!

WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool

Old Town Key West
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.
$239 nightly
The price is $265
Dec 2 - Dec 3
Total with taxes and fees
WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool
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 $226 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.