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Fleming Key Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Fleming Key vacation rentals

House | 2 bedrooms

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
$473 nightly
The price is $532
Jun 22 - Jun 23
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
Pool

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (60 reviews)
"Friendly host and unique location"
United States
Scott
$364 nightly
The price is $404
Jun 22 - Jun 23
Total with taxes and fees
Living the Dream Key West Style
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (188 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
$224 nightly
The price is $252
Jun 22 - Jun 23
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Outdoor pool

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.4 out of 10, Good, (38 reviews)
"Our stay was good. Yacht was as described. There were fans provided in the bedrooms downstairs so we were comfortable. There is an info book provided which helped a lot. "
United States
Faith C.
$370 nightly
The price is $410
Jun 22 - Jun 23
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Beach nearby

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.2 out of 10, Wonderful, (46 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
$388 nightly
The price is $432
Jun 21 - Jun 22
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Beach nearby, beach towels

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.4 out of 10, Exceptional, (113 reviews)
"Clean, quiet place very safe. "
United States
Suzanne L.
$398 nightly
The price is $442
Jun 22 - Jun 23
Total with taxes and fees
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Exterior

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"It was great. House was amazing"
United States
Ernest H.
$1,588 nightly
The price is $1,765
Jun 21 - Jun 22
Total with taxes and fees
Springtide House at Lunara Bay
2 bedrooms, free WiFi, bed sheets

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
9.2 out of 10, Wonderful, (11 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
$319 nightly
The price is $354
Jul 13 - Jul 14
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
TV, offices

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
United States
Wilbert C.
$1,798 nightly
The price is $1,995
Jun 29 - Jun 30
Total with taxes and fees
Capmar House at Lunara Bay
Property grounds

The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (51 reviews)
"Very clean place. Host was very nice and accommodating. Had a wonderful stay. "
United States
Amy B.
$461 nightly
The price is $511
Jul 2 - Jul 3
Total with taxes and fees
The Salt Cay | Updated! Stunning Sunset View, Pool
House | Exterior

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
$839 nightly
The price is $944
Jun 21 - Jun 22
Total with taxes and fees
Resort View 3BR Residence
Beach

Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (32 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
$491 nightly
The price is $545
Jun 29 - Jun 30
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
Property grounds

The Butterfly Nest | Newly Updated w/ Shared Pool

The Butterfly Nest | Newly Updated w/ Shared Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"Clean property, comfortable beds. Would stay here again. "
United States
Ken F.
$441 nightly
The price is $489
Jun 30 - Jul 1
Total with taxes and fees
The Butterfly Nest | Newly Updated w/ Shared Pool
Exterior detail

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, (132 reviews)
"Great place to stay"
United States
walter l.
$268 nightly
The price is $297
Jun 23 - Jun 24
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Property grounds

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

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (31 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
$441 nightly
The price is $489
Jun 28 - Jun 29
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
TV, offices

Waterlane House at Lunara Bay

Waterlane House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great!"
United States
Elaine O.
$1,630 nightly
The price is $1,809
Jun 24 - Jun 25
Total with taxes and fees
Waterlane House at Lunara Bay
Exterior

Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (44 reviews)
"Great communication….we have stayed here several times and will be back! "
United States
james f.
$1,667 nightly
The price is $1,851
Jun 29 - Jun 30
Total with taxes and fees
Aquaria House at Lunara Bay
Pool

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (42 reviews)
"Had to book here last minute due to first booking being canceled night before check-in! What a great experience this was. Host was very easy to deal with and would respond back very quickly. Even willing to let is get in a little early due to our situation. Glad we booked here! ALSO the house and property are great! Very well maintained and clean! "
United States
Matt P.
$2,593 nightly
The price is $2,877
Jun 29 - Jun 30
Total with taxes and fees
Suncoast House at Lunara Bay
Pool

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
$538 nightly
The price is $597
Jun 23 - Jun 24
Total with taxes and fees
Paradise found
Property grounds

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"A good value for the travel dollar."
United States
sandra j.
$419 nightly
The price is $467
Jun 21 - Jun 22
Total with taxes and fees
The Cat Island Suite | Charmingly Renovated w/ 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

The Laureate Key West

The Laureate Key West

8/10 Good
"The hotel was nice, but I’m not sure why there was a “resort fee” or what it covered. As someone who didn’t know Key West, I assumed this hotel has beach access from the pictures. I would say the pictures online were very misleading. The room was nice though, just felt like I should have done more research into there not actually being swimmable beaches in Key West."
Tonya 4-night trip
Posted 1 hour ago
The Laureate Key West

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 $252 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.

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