Fleming Key Vacation Rentals from ￥37,742: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Fleming Key vacation rentals

A row of floating houses with balconies, connected by walkways, on calm water.

1. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

￥46,302 total

includes taxes & fees

Oct 31 - Nov 1

A white building with a covered porch and a palm tree.

2. Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West

Laura D.

￥37,742 total

includes taxes & fees

Oct 29 - Oct 30

A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

3. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Old Town Key West

Amanda G.

￥50,397 total

includes taxes & fees

Oct 28 - Oct 29

A courtyard with a gravel path, palm trees, and a building with a white facade.

4. Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval

Old Town Key West

Stephanie

￥65,960 total

includes taxes & fees

Oct 28 - Oct 29

A tropical garden pathway leading to a building with a yellow facade and green shutters.

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

Old Town Key West

walter l.

￥68,113 total

includes taxes & fees

Nov 22 - Nov 23

A narrow brick pathway flanked by white buildings with potted plants and a bench.

6. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Old Town Key West

Jay M.

￥58,625 total

includes taxes & fees

Oct 25 - Oct 26

A small, private entrance to a house with a brick pathway leading to a door.

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

Old Town Key West

Jamie F.

￥61,411 total

includes taxes & fees

Oct 26 - Oct 27

A multi-level wooden house with a blue staircase and white railings.

8. Underwater Cabana at Custom House Inn | On Duval!

Key West Historic District

Colleen L.

￥70,800 total

includes taxes & fees

Oct 25 - Oct 26

A wooden deck with a thatched roof structure, a pool, lounge chairs, and a bar area.

9. Waterfront Dock Pool Key West Near Duval

Meadows

Chrystalbelle R.

￥76,853 total

includes taxes & fees

Nov 2 - Nov 3

A living room with a flat-screen TV, a ceiling fan, a teal sofa, and a view of the marina through large windows.

10. Waterfront Dock Pool Condo Near Duval St Pet OK

Meadows

Amber G.

￥70,446 total

includes taxes & fees

Oct 25 - Oct 26

A bedroom with a bed, a ceiling fan, a nightstand with a lamp, a window with curtains, and a view of the outside.

11. Waterfront Condo Dock Pool Near Duval St

Meadows

Patsy K.

￥67,564 total

includes taxes & fees

Oct 25 - Oct 26

A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

12. Chagall's Corner | Newly Remodeled!

Old Town Key West

Maria B.

￥54,694 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.

13. Resort View 1BR Suite

Key West

Michael

￥54,826 total

includes taxes & fees

Oct 25 - Oct 26

A covered porch with white wooden railings, wicker furniture, and hanging lanterns.

14. Duval Delight | Recently Remodeled Condo on Duval!

Old Town Key West

Jennifer

￥79,183 total

includes taxes & fees

Nov 1 - Nov 2

A wooden deck with a large tree, outdoor seating, and a marina in the background.

15. Poolside Cottage #412

Key West

shannon b.

￥48,193 total

includes taxes & fees

Oct 26 - Oct 27

A pool area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

16. Leo's Lodge | Newly Updated!

Old Town Key West

Blake

￥54,694 total

includes taxes & fees

Nov 22 - Nov 23

17. VanGogh Studio | Updated, Old Town, Heated Pool

Old Town Key West

Jesse M.

￥66,248 total

includes taxes & fees

Oct 25 - Oct 26

A modern living room with a sofa, coffee table, and a painting of a beach scene.

18. The Saint Kitts Suite | Breathtaking View, Heated Pool

Key West

Rolando

￥79,039 total

includes taxes & fees

Oct 28 - Oct 29

A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

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

Key West

Teri K.

￥79,039 total

includes taxes & fees

Oct 26 - Oct 27

A modern living room with a grey sofa, wooden flooring, a ceiling fan, and framed artwork on the walls.

20. Kingfish Keep | Lively Escape on Duval! Balcony!

Old Town Key West

Andrew M.

￥75,205 total

includes taxes & fees

Oct 25 - Oct 26

View all properties

Find vacation rentals that suit your style

Apartments

Condos

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Fleming Key Hotel Reviews

Beachside Resort & Residences

10/10 Excellent

"We’ve stayed at this resort 3 times over the last few years and the room, staff, and concierge were great every time. We will be booking at this location again."

Southernmost Beach Resort and Guesthouses

8/10 Good

"Loved the wristband key to the room. The room was clean, the bed was comfortable. The noise from the A/C was annoying…off and on all night long. The water/ice machine outside our room did not work, however, we loved the fruit flavored water in the lobby. Coffee machine in room was nice feature. We visited all 3 pools. They were nice but not cleaned as should be. One was pretty cloudy so we didn’t go back to that one. Seems like the drinkers didn’t take time out to use restrooms. All in all, it was a nice place at the southern end of Duval St."

Margaritaville Beach House Key West

8/10 Good

"The resort overall was great! Everyone friendly. Very clean. Food was good. Although staying all week, it would be nice if they had a few daily specials so you don’t have the same menu everyday. Well organized. A few things I would like to suggest or point out. The rooms did not get cool enough to be comfortable. I thought it was just ours because we were facing the sun all day but others said the same thing. The couch has to go! Very uncomfortable and looks like it’s missing pieces. The room was very clean and looked great. I wouldn’t even consider these bad just what my experience."

Find out more about Fleming Key

Search for holiday rentals in Fleming Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Fleming Key using one of the methods below:

View our selection of featured holiday rentals in Fleming Key
Use the map to find apartments and other holiday homes in the Fleming Key neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Fleming Key while they last

Look no further and take a look at our great range of rental properties in Fleming Key!

Explore a world of travel with Expedia

Key West Vacations

Big Pine Key Vacation Rentals

Expedia's Latest Trends

Hotels

Flights

Flights to Stock Island

Cars

Activities

Things to do in Shell Island

Packages

General

Fleming Key Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Fleming Key vacation rentals

1. Aqua Lodges at Hurricane Hole Marina

2. Steps from Duval, Pool on Site & Bikes Included!

3. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

4. Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval

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

6. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

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

8. Underwater Cabana at Custom House Inn | On Duval!

9. Waterfront Dock Pool Key West Near Duval

10. Waterfront Dock Pool Condo Near Duval St Pet OK

11. Waterfront Condo Dock Pool Near Duval St

12. Chagall's Corner | Newly Remodeled!

13. Resort View 1BR Suite

14. Duval Delight | Recently Remodeled Condo on Duval!

15. Poolside Cottage #412

16. Leo's Lodge | Newly Updated!

17. VanGogh Studio | Updated, Old Town, Heated Pool

18. The Saint Kitts Suite | Breathtaking View, Heated Pool

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

20. Kingfish Keep | Lively Escape on Duval! Balcony!

Find vacation rentals that suit your style

Top Fleming Key Hotel Reviews

Beachside Resort & Residences

Find out more about Fleming Key

Explore a world of travel with Expedia

Expedia's Latest Trends

Go further with the Expedia app