Fleming Key Vacation Rentals

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

Vacation Rentals in Fleming Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is ¥15,388
¥43,488 total
includes taxes & fees
Nov 30 - Dec 1
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, (317)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is ¥37,121
¥47,057 total
includes taxes & fees
Dec 16 - Dec 17
Hyatt Vacation Club at Sunset Harbor, Key West

Living the Dream Key West Style

Stock Island
9.8 out of 10, Exceptional, (34)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
The price is ¥42,023
¥53,212 total
includes taxes & fees
Dec 8 - Dec 9
Living the Dream Key West Style

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

Stock Island
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 ¥39,040
¥78,236 total
includes taxes & fees
Nov 27 - Nov 28
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Poolside Cottage #411

Key West
9.8 out of 10, Exceptional, (53)
"Clean and as advertised "
United States
John H.
The price is ¥26,001
¥47,737 total
includes taxes & fees
Dec 4 - Dec 5
Poolside Cottage #411

Comfortable Condo with Pool, Private Balcony, & Beach Access

Beachside
8.6 out of 10, Excellent, (137)
"Nice area, location, and wonderful apartment!"
United States
Harald P.
The price is ¥23,060
¥90,108 total
includes taxes & fees
Nov 30 - Dec 1
Comfortable Condo with Pool, Private Balcony, & Beach Access

Paradise found

Stock Island
9.8 out of 10, Exceptional, (31)
"Nice stay and budget friendly. Hard to find a place to house 5 guys but this an accomplished that easily. Conveniently located to the airport and the restaurants in the area were great. If your trip in Key West involves the marina, the marina is just behind the hogfish grill. "
United States
Mike Q.
Paradise found

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
The price is ¥43,495
¥62,213 total
includes taxes & fees
Dec 1 - Dec 2
Island View 1BR Residence With Balcony

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Old Town Key West
10.0 out of 10, Exceptional, (24)
"We had a wonderful stay here with our kids. Can’t beat the location."
United States
Julia P.
The price is ¥21,550
¥61,009 total
includes taxes & fees
Dec 17 - Dec 18
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pool, Free Parking & Pet Friendly - The Barbados

Key West
9.2 out of 10, Wonderful, (31)
"4 nights, was perfect"
United States
Ryan M.
The price is ¥31,076
¥83,703 total
includes taxes & fees
Dec 1 - Dec 2
Pool, Free Parking & Pet Friendly - The Barbados

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

Beachside
9.0 out of 10, Wonderful, (104)
"Very clean and beds are so comfortable. "
United States
Donny G.
The price is ¥63,089
¥142,706 total
includes taxes & fees
Dec 7 - Dec 8
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis

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

Key West
10.0 out of 10, Exceptional, (24)
"Perfect location. Close to pool and less than 15 minutes to Duval. "
United States
Candice E.
The price is ¥17,726
¥54,932 total
includes taxes & fees
Nov 30 - Dec 1
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony & Pool!

Poolside Cottage #412

Key West
9.2 out of 10, Wonderful, (27)
"The property and our place was really nice. Would definitely stay again. "
United States
Sarah M.
The price is ¥26,001
¥46,488 total
includes taxes & fees
Dec 4 - Dec 5
Poolside Cottage #412

Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK

Old Town Key West
9.0 out of 10, Wonderful, (100)
"Nice place, accurate description. "
United States
Sean F.
The price is ¥19,364
¥56,366 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK

Private Parking & Waterfront - Grand Marina Suite

Stock Island
9.6 out of 10, Exceptional, (28)
"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 ¥47,061
¥72,573 total
includes taxes & fees
Dec 1 - Dec 2
Private Parking & Waterfront - Grand Marina Suite

Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale

Old Town Key West
9.4 out of 10, Exceptional, (186)
"Perfectly located!!! Clean, comfy, and cute! Super secure as well! Only a block off Duvall! Will definitely stay here again!"
United States
Christine H.
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale

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

Key West
8.6 out of 10, Excellent, (140)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is ¥21,394
¥57,801 total
includes taxes & fees
Dec 1 - Dec 2
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

The Island Suite at KW Vacation

Key West Historic District
10.0 out of 10, Exceptional, (116)
"Great location. Very clean. Great host communication. Will definitely come back!"
United States
Morgan D.
The price is ¥36,229
¥65,334 total
includes taxes & fees
Dec 2 - Dec 3
The Island Suite at KW Vacation

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Meadows
9.2 out of 10, Wonderful, (15)
"Great location"
United States
Angie j.
The price is ¥18,115
¥67,404 total
includes taxes & fees
Dec 4 - Dec 5
Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Palm - Beach Houses Key West

Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"We had the most wonderful time staying in the Palm bungalow. It is just steps away from the pool oasis where we spent our days relaxing and grilling. We then drove into Key West in the evenings. Very convenient location where you get the best of both worlds of serenity and relaxation, but also close enough to drive into town. The sunrises, and the waterfront and beachfront views are beautiful. We enjoyed the natural setting, felt like we were in our own little paradise. The host Cadmier is...
United States
Nicole H.
Palm - Beach Houses Key West
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

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!