Fleming Key Vacation Rentals

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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
$283 nightly
The price is $319
Nov 11 - Nov 12
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
$257 nightly
The price is $289
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Old Town Key West
9.6 out of 10, Exceptional, (29)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
United States
Dianna F.
$319 nightly
The price is $351
Nov 18 - Nov 19
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

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

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

Meadows
10.0 out of 10, Exceptional, (23)
"My husband and I stayed at this property for our anniversary week. "
United States
Claudia S.
$384 nightly
The price is $399
Dec 1 - Dec 2
Total with taxes and fees
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

Old Town Key West
9.6 out of 10, Exceptional, (141)
"Wonderful and quiet property but in walking distance to the excitement. Great communication and easy check in and check out. We will be back!"
United States
Krista
$213 nightly
The price is $236
Nov 12 - Nov 13
Total with taxes and fees
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

Comfortable Condo with Pool, Private Balcony, & Beach Access

Beachside
8.6 out of 10, Excellent, (137)
"Place was perfect for a family of 6. Very nice layout. Pool and spa were very nice. You could look out and see the ocean in the distance but no real beach access. It was visible but you can’t get to it from the property. Although it is right up the street on either side of the property so that was nice. The only downfall to this place is we got eaten up by what seems to have been fleas."
United States
Dorothy R.
$519 nightly
The price is $575
Nov 11 - Nov 12
Total with taxes and fees
Comfortable Condo with Pool, Private Balcony, & Beach Access

JULIE ~ Adult Only, 1st Floor King Bedroom w/ Shared Pool, Scarlet Mango Inn!

Old Town Key West
10.0 out of 10, Exceptional, (75)
"Excellent."
United States
Matt M.
$279 nightly
The price is $310
Nov 10 - Nov 11
Total with taxes and fees
JULIE ~ Adult Only, 1st Floor King Bedroom w/ Shared Pool, Scarlet Mango Inn!

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

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

Stock Island
7.8 out of 10, Good, (23)
"The resort was amazing- we really enjoyed the house boat and Marina life- thank you for sharing and your great communication"
United States
Maureen M.
$451 nightly
The price is $501
Nov 9 - Nov 10
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Poolside Cottage #411

Key West
9.8 out of 10, Exceptional, (53)
"Nice area, quiet and clean"
United States
Gary S.
$275 nightly
The price is $305
Nov 10 - Nov 11
Total with taxes and fees
Poolside Cottage #411

The Seagate Estate at Lunara Bay

Raccoon Key
10.0 out of 10, Exceptional, (17)
"The perfect House , everything was good "
United States
CARLOS G.
$1,427 nightly
The price is $1,583
Nov 10 - Nov 11
Total with taxes and fees
The Seagate Estate at Lunara Bay

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

Old Town Key West
9.8 out of 10, Exceptional, (96)
"Everything you need to explore Key West"
United States
Stephanie P.
$275 nightly
The price is $305
Nov 12 - Nov 13
Total with taxes and fees
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

Waterfront Luxury Home - Tidelands House

2.0 star property
Raccoon Key
$2,689 nightly
The price is $3,025
Nov 10 - Nov 11
Total with taxes and fees
Waterfront Luxury Home - Tidelands House

Poolside Cottage #412

Key West
9.2 out of 10, Wonderful, (26)
"very nice bungalow right in front of the pool. Well maintained and comfortable. Was a great place to stay."
United States
DONALD H.
$275 nightly
The price is $305
Nov 11 - Nov 12
Total with taxes and fees
Poolside Cottage #412

Palm - Beach Houses Key West

Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
United States
Crystal G.
$1,390 nightly
The price is $1,530
Nov 19 - Nov 20
Total with taxes and fees
Palm - Beach Houses Key West

Private Parking & Waterfront - Grand Marina Suite

Stock Island
9.6 out of 10, Exceptional, (28)
"safe and quite"
United States
Wes
$417 nightly
The price is $463
Nov 11 - Nov 12
Total with taxes and fees
Private Parking & Waterfront - Grand Marina Suite

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

Old Town Key West
9.0 out of 10, Wonderful, (100)
"Walk to everything. Had a great stay in this cute key west cottage. Beds were very comfortable and needed after a long day of fun. Would stay here again."
United States
Trista P.
$354 nightly
The price is $392
Nov 13 - Nov 14
Total with taxes and fees
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK

Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking

Key West
9.2 out of 10, Wonderful, (156)
"Nice place to stay with washer/dryer and parking."
United States
Bobbi M.
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Key West
8.8 out of 10, Excellent, (201)
"We enjoyed our stay. Location was perfect and just a short ride from the downtown activity. Rooms were adequate and parking was perfect. Our stay was sweet and short"
United States
kateryna s.
$260 nightly
The price is $289
Nov 12 - Nov 13
Total with taxes and fees
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
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.
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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.