Fleming Key Vacation Rentals

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Our top choices for Fleming Key vacation rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (172)
"Location , staff , and aqua lodge were perfect."
United States
William
$283 nightly
The price is $319
Jan 11 - Jan 12
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
$568 nightly
The price is $639
Jan 7 - Jan 8
Total with taxes and fees
Ocean Front One Bedroom Residence

Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
$1,277 nightly
The price is $1,436
Jan 7 - Jan 8
Total with taxes and fees
Coconut Mallory Marina and Resort Condo

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
$1,505 nightly
The price is $1,693
Jan 12 - Jan 13
Total with taxes and fees
Contra House Key West

The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
$503 nightly
The price is $565
Jan 7 - Jan 8
Total with taxes and fees
The Bartlum Luxury Studio In Prime Location

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
$628 nightly
The price is $707
Jan 11 - Jan 12
Total with taxes and fees
Mesa House Uno by Brightwild Perfect Location

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
$607 nightly
The price is $683
Jan 7 - Jan 8
Total with taxes and fees
The Grenada Suite Pool View Private Balcony

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
$698 nightly
The price is $786
Jan 13 - Jan 14
Total with taxes and fees
New Coastal Rose - Bright Loft With High Ceilings

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$582 nightly
The price is $654
Jan 7 - Jan 8
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
$704 nightly
The price is $792
Jan 7 - Jan 8
Total with taxes and fees
Sea Breeze by Brightwild Off-street Parking

Poolside Paradise by Brightwild Heated Pool

Poolside Paradise by Brightwild Heated Pool
2.0 star property
Old Town Key West
Poolside Paradise by Brightwild Heated Pool

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
$2,584 nightly
The price is $2,906
Jan 13 - Jan 14
Total with taxes and fees
The Fairhaven House at Solaire Lunara Bay

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
$766 nightly
The price is $862
Jan 11 - Jan 12
Total with taxes and fees
Poolside Suite by Brightwild Pvt Pool Parking

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
$757 nightly
The price is $852
Jan 7 - Jan 8
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront

Cloud Suite on Duval Luxury Condo Epic Location

Cloud Suite on Duval Luxury Condo Epic Location
2.0 star property
Old Town Key West
$844 nightly
The price is $950
Jan 11 - Jan 12
Total with taxes and fees
Cloud Suite on Duval Luxury Condo Epic Location

Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1)
$834 nightly
The price is $939
Jan 7 - Jan 8
Total with taxes and fees
Duval Dream Loft by Brightwild Right on Duval

The Trinidad by Brightwild Pool View Parking

The Trinidad by Brightwild Pool View Parking
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"Our family spent one night at Key West and we fully enjoyed our stay here. Room is very clean, stylish and spacious. Beds are comfortable."
United States
Xiulin
$645 nightly
The price is $726
Jan 13 - Jan 14
Total with taxes and fees
The Trinidad by Brightwild Pool View Parking

The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
2.0 star property
Raccoon Key
$2,163 nightly
The price is $2,434
Jan 7 - Jan 8
Total with taxes and fees
The Joyrise House at Solaire Lunara Bay

New Rose Retreat - Pool Parking

New Rose Retreat - Pool Parking
2.0 star property
Key West Historic District
$1,387 nightly
The price is $1,561
Jan 15 - Jan 16
Total with taxes and fees
New Rose Retreat - Pool Parking

Commodore s Cove by Brightwild Epic Location

Commodore s Cove by Brightwild Epic Location
2.0 star property
Key West Historic District
$1,733 nightly
The price is $1,950
Jan 14 - Jan 15
Total with taxes and fees
Commodore s Cove by Brightwild Epic Location
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 $319 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.