Fleming Key Holiday Rentals

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Our top choices for Fleming Key holiday 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 reviews)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is AU$476
includes taxes & fees
11 Jan - 12 Jan
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 reviews)
"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 AU$746
includes taxes & fees
25 Jan - 26 Jan
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 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is AU$2,919
includes taxes & fees
15 Jan - 16 Jan
Palm - Beach Houses Key West

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is AU$4,234
includes taxes & fees
14 Jan - 15 Jan
Waterfront Luxury Home - Tidelands House

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (53 reviews)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
The price is AU$560
includes taxes & fees
13 Jan - 14 Jan
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 reviews)
"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.
The price is AU$551
includes taxes & fees
11 Jan - 12 Jan
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 reviews)
"The property and our place was really nice. Would definitely stay again. "
United States
Sarah M.
The price is AU$563
includes taxes & fees
15 Jan - 16 Jan
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 reviews)
"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
The price is AU$703
includes taxes & fees
24 Jan - 25 Jan
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
9.6 out of 10, Exceptional, (27 reviews)
"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
The price is AU$920
includes taxes & fees
25 Jan - 26 Jan
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 reviews)
"well maintained, clean, easy to access"
United States
Raj P.
The price is AU$3,785
includes taxes & fees
11 Jan - 12 Jan
Larkshine 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 reviews)
"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.
The price is AU$938
includes taxes & fees
31 Jan - 1 Feb
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 reviews)
"Amazing house! Spacious, great pool, & good location "
United States
Paige G.
The price is AU$3,047
includes taxes & fees
11 Jan - 12 Jan
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 reviews)
"Nice place "
United States
Pawel
The price is AU$1,246
includes taxes & fees
26 Jan - 27 Jan
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, (112 reviews)
"Great value stay"
United States
Mike B.
The price is AU$685
includes taxes & fees
25 Jan - 26 Jan
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 reviews)
"Awesome! Would stay here again!"
United States
Rebecca W.
The price is AU$1,140
includes taxes & fees
19 Jan - 20 Jan
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 reviews)
"Very clean and stocked. Pleasant experience!"
United States
Iris H.
The price is AU$3,047
includes taxes & fees
11 Jan - 12 Jan
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 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is AU$980
includes taxes & fees
12 Jan - 13 Jan
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 reviews)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
The price is AU$989
includes taxes & fees
26 Jan - 27 Jan
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 reviews)
"We really enjoyed the property. "
United States
Shayna
The price is AU$563
includes taxes & fees
13 Jan - 14 Jan
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fleming Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fleming Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fleming Key holiday rentals we have selected for you start as low as AU$468 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fleming Key rentals

At Expedia, we put the best Fleming Key holiday 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 holiday.

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.