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
9.0 out of 10, Wonderful, (182 reviews)
"Great stay better than we expected "
Canada
Jordan
The price is CA $220
CA $479 total
includes taxes & fees
May 8 - May 9
Aqua Lodges at Hurricane Hole Marina

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
8.6 out of 10, Excellent, (7 reviews)
"If you are looking for a fun adventure stay this is the place for you, host was amazing from start to finish. Ocean views at sunset are amazing!"
United States
Barry
The price is CA $280
CA $487 total
includes taxes & fees
Apr 14 - Apr 15
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

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

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.6 out of 10, Good, (34 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 CA $346
CA $689 total
includes taxes & fees
May 13 - May 14
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is CA $414
CA $849 total
includes taxes & fees
Apr 14 - Apr 15
Paradise found

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (57 reviews)
"everything was perfect"
United States
Kathy A
The price is CA $443
CA $562 total
includes taxes & fees
Apr 16 - Apr 17
Living the Dream Key West Style

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 CA $569
CA $967 total
includes taxes & fees
Apr 19 - Apr 20
Grand Marina Suite by Brightwild Waterfront

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina
Stock Island
The price is CA $137
CA $953 total
includes taxes & fees
Apr 13 - Apr 14
Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (47 reviews)
"Great place with great location , good for families "
United States
Dennys P.
The price is CA $301
CA $753 total
includes taxes & fees
Apr 13 - Apr 14
The Salt Cay | Updated! Stunning Sunset View, Pool

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (43 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is CA $301
CA $753 total
includes taxes & fees
Apr 15 - Apr 16
The Cat Island Suite | Charmingly Renovated w/ Pool

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, (130 reviews)
"Amazing place to stay, excellent experience!!!"
United States
Brad
The price is CA $282
CA $566 total
includes taxes & fees
Apr 14 - Apr 15
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

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
9.6 out of 10, Exceptional, (102 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is CA $275
CA $558 total
includes taxes & fees
Apr 14 - Apr 15
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"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 traveller
The price is CA $1,106
CA $2,366 total
includes taxes & fees
Apr 14 - Apr 15
Capmar House at Lunara Bay

Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (32 reviews)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
The price is CA $544
CA $1,041 total
includes taxes & fees
Apr 19 - Apr 20
Grand Marina Suite - Poolside & Waterfront Condo

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (45 reviews)
"It was great. House was amazing"
United States
Ernest H.
The price is CA $1,106
CA $2,366 total
includes taxes & fees
Apr 14 - Apr 15
Springtide House at Lunara Bay

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (62 reviews)
"This was a beautiful property, great location and awesome amenities. We loved it and will highly recommend it! "
United States
Kim H.
The price is CA $311
CA $527 total
includes taxes & fees
Apr 23 - Apr 24
Poolside Cottage #411

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is CA $454
CA $625 total
includes taxes & fees
Apr 13 - Apr 14
Resort View 1BR Suite With Direct Pool Access

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

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
9.8 out of 10, Exceptional, (29 reviews)
"Pleasant stay - had a couple issues that we needed to be fixed that were resolved as quickly as possible. "
United States
Christina M.
The price is CA $301
CA $753 total
includes taxes & fees
Apr 20 - Apr 21
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (22 reviews)
"Great place and great hosts. However the pool never heated and couldn’t get anyone out to look at it. Overall an amazing stay and would definitely return."
United States
Austin S.
The price is CA $1,106
CA $2,366 total
includes taxes & fees
May 10 - May 11
The Seagate Estate at Lunara Bay

Leo's Lodge | Newly Updated!

Leo's Lodge | Newly Updated!
Old Town Key West
8.6 out of 10, Excellent, (26 reviews)
"Very nice facility and pool; bathroom was small for large person."
United States
James
The price is CA $171
CA $492 total
includes taxes & fees
Apr 15 - Apr 16
Leo's Lodge | Newly Updated!

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (42 reviews)
"Room had everything we needed!Owners and staff were very responsive and offered free shuttle to/from the airport!"
United States
Timothy P.
The price is CA $171
CA $492 total
includes taxes & fees
Apr 29 - Apr 30
VanGogh Studio | Updated, Old Town, Heated Pool
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Fleming Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.