Fleming Key Vacation Rentals

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (175 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
$292 nightly
The price is $329
Feb 11 - Feb 12
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
$2,689 nightly
The price is $3,025
Feb 8 - Feb 9
Total with taxes and fees
Waterfront Luxury Home - Tidelands House

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

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
8.0 out of 10, Very Good, (27 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
$457 nightly
The price is $507
Feb 9 - Feb 10
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
$1,427 nightly
The price is $1,583
Feb 8 - Feb 9
Total with taxes and fees
The Seagate Estate at Lunara Bay

Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Place is perfect"
United States
Ryan S.
$408 nightly
The price is $453
Mar 2 - Mar 3
Total with taxes and fees
Balcony, Pool, & Near Duval - Curry House Room 8

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
$1,467 nightly
The price is $1,623
Feb 8 - Feb 9
Total with taxes and fees
The Lighthouse - Beach Houses Key West

Mirador House at Lunara Bay

Mirador House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (34 reviews)
"Fantastic property! Fantastic hosts! Fantastic pool! Would highly recommend staying here, we had an amazing time. "
United States
Claudia S.
$2,258 nightly
The price is $2,505
Feb 18 - Feb 19
Total with taxes and fees
Mirador House at Lunara Bay

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
$1,372 nightly
The price is $1,519
Feb 20 - Feb 21
Total with taxes and fees
Private and Exclusive Florida Keys Getaway

Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home
Raccoon Key
9.6 out of 10, Exceptional, (32 reviews)
"The house was very clean and the neighborhood was in a perfect area and the neighbors were very friendly. Perfect get away!"
United States
Rachael S.
$1,535 nightly
The price is $1,704
Feb 8 - Feb 9
Total with taxes and fees
Mastway House at Lunara Bay - Wellness Home

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, (184 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
Low Rates.& spec. early & late book spec. & 10% wk stays & close all& beach!

Altair House at Lunara Bay

Altair House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (12 reviews)
"Great house. Large space, everything you need is there. "
United States
CRIMSON A.
$1,998 nightly
The price is $2,217
Feb 5 - Feb 6
Total with taxes and fees
Altair House at Lunara Bay

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
Starlight Serenity - Hideaway w Stunning Views

Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
Key West
9.0 out of 10, Wonderful, (140 reviews)
"Great stay"
United States
Jason U.
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

Poolside Cottage #412

Poolside Cottage #412
Key West
9.2 out of 10, Wonderful, (29 reviews)
"Everything you need for a great stay!!"
United States
Karen D.
$425 nightly
The price is $472
Feb 26 - Feb 27
Total with taxes and fees
Poolside Cottage #412

Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (40 reviews)
"Our family had a wonderful time at this location. Fishing off the dock and swimming was fun for the kids. A quiet location with a short drive to all attractions."
United States
Nola S.
$1,427 nightly
The price is $1,583
Feb 8 - Feb 9
Total with taxes and fees
Aquaria House at Lunara Bay

Seagull Suite | Inviting Studio, Steps From Duval

Seagull Suite | Inviting Studio, Steps From Duval
Old Town Key West
9.8 out of 10, Exceptional, (23 reviews)
"Great little place, perfect for southernmost area."
United States
Lee G.
$672 nightly
The price is $746
Mar 2 - Mar 3
Total with taxes and fees
Seagull Suite | Inviting Studio, Steps From Duval

Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
9.8 out of 10, Exceptional, (27 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
$1,541 nightly
The price is $1,710
Feb 18 - Feb 19
Total with taxes and fees
Evershore Estate at Lunara Bay | Wellness Home

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
$696 nightly
The price is $773
Feb 6 - Feb 7
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo

Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"Good amenities, nice for a weekend get away"
United States
Alexander B.
$607 nightly
The price is $674
Feb 27 - Feb 28
Total with taxes and fees
Sunny Condo with WiFi, Hot Tub, Pool & Tennis

SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community Pool!

SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community Pool!
Old Town Key West
9.8 out of 10, Exceptional, (100 reviews)
"The suite was super clean and quiet. Pool is sparkly and covered just enough for relief from the sun! "
United States
Jennifer F.
$541 nightly
The price is $600
Feb 8 - Feb 9
Total with taxes and fees
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community 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.
Save an average of 15% on thousands of hotels when you're signed in

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 $311 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.