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

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

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
$457 nightly
The price is $507
Jan 25 - Jan 26
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Palm - Beach Houses Key West

Palm - Beach Houses Key West
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
$1,787 nightly
The price is $1,968
Jan 14 - Jan 15
Total with taxes and fees
Palm - Beach Houses Key West

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
$2,471 nightly
The price is $2,780
Jan 11 - Jan 12
Total with taxes and fees
Waterfront Luxury Home - Tidelands House

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
$441 nightly
The price is $489
Feb 5 - Feb 6
Total with taxes and fees
Poolside Cottage #411

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

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Key West
8.8 out of 10, Excellent, (207)
"Good stay, everything was comfortable and ready to check in along with the typical amenities you would see at traditional hotels. Only stayed one night but there was a strong odor in the apartment, may have been from previous guests’ cooking but wasn’t unpleasant. Would stay again. "
United States
Juan E.
$325 nightly
The price is $361
Jan 11 - Jan 12
Total with taxes and fees
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Poolside Cottage #412

Poolside Cottage #412
Key West
9.2 out of 10, Wonderful, (28)
"The property and our place was really nice. Would definitely stay again. "
United States
Sarah M.
$344 nightly
The price is $382
Jan 7 - Jan 8
Total with taxes and fees
Poolside Cottage #412

Low Rates.& spec. early & late book spec. & 10% wk stays & close all& beach!

Low Rates.& spec. early & late book spec. & 10% wk stays & close all& beach!
Old Town Key West
9.0 out of 10, Wonderful, (181)
"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! "
United States
ALISHA
$463 nightly
The price is $514
Jan 24 - Jan 25
Total with taxes and fees
Low Rates.& spec. early & late book spec. & 10% wk stays & close all& beach!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (26)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
$421 nightly
The price is $463
Jan 8 - Jan 9
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Larkshine House at Lunara Bay

Larkshine House at Lunara Bay
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (8)
"well maintained, clean, easy to access"
United States
Raj P.
$2,204 nightly
The price is $2,448
Jan 7 - Jan 8
Total with taxes and fees
Larkshine House at Lunara Bay

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
$1,531 nightly
The price is $1,700
Jan 21 - Jan 22
Total with taxes and fees
Capmar House at Lunara Bay

Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking

Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking
Key West
9.4 out of 10, Exceptional, (133)
"This was a wonderful place to stay. We had a great time and it was convenient to reach downtown from here. Will stay again"
United States
Bess Y.
$577 nightly
The price is $640
Jan 31 - Feb 1
Total with taxes and fees
Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking

Floralee House at Lunara Bay

Floralee House at Lunara Bay
2.0 star property
Raccoon Key
9.8 out of 10, Exceptional, (8)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
$1,823 nightly
The price is $2,029
Jan 12 - Jan 13
Total with taxes and fees
Floralee House at Lunara Bay

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
$773 nightly
The price is $870
Jan 7 - Jan 8
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront

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

SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (111)
"Great value stay"
United States
Mike B.
$304 nightly
The price is $337
Jan 7 - Jan 8
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!

Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Stock Island
10.0 out of 10, Exceptional, (37)
"Awesome! Would stay here again!"
United States
Rebecca W.
$695 nightly
The price is $771
Jan 19 - Jan 20
Total with taxes and fees
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!

Palmgale Estate at Lunara Bay

Palmgale Estate at Lunara Bay
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (8)
"Very clean and stocked. Pleasant experience!"
United States
Iris H.
$1,823 nightly
The price is $2,029
Jan 12 - Jan 13
Total with taxes and fees
Palmgale Estate at Lunara Bay

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.8 out of 10, Exceptional, (117)
"Great location, close to everything family had a great time."
United States
rafael m.
$584 nightly
The price is $648
Jan 7 - Jan 8
Total with taxes and fees
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (30)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
$886 nightly
The price is $983
Jan 26 - Jan 27
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.4 out of 10, Exceptional, (96)
"We really enjoyed the property. "
United States
Shayna
$297 nightly
The price is $330
Jan 7 - Jan 8
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
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.