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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Fleming Key condo rentals

A heated pool
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (98)
"Very clean and private. We enjoyed our time and would return."
United States
Janine W.
The price is ￥28,925
￥59,892 total
includes taxes & fees
Dec 21 - Dec 22
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
A heated pool
Andy’s Attic | Budget-Friendly!

Andy’s Attic | Budget-Friendly!

Andy’s Attic | Budget-Friendly!
Old Town Key West
8.4 out of 10, Very Good, (25)
"great location"
United States
Carol
The price is ￥17,106
￥44,535 total
includes taxes & fees
Dec 20 - Dec 21
Andy’s Attic | Budget-Friendly!
A heated pool
Carey’s Corner | Updated Studio with Heated Pool

Carey’s Corner | Updated Studio with Heated Pool

Carey’s Corner | Updated Studio with Heated Pool
Old Town Key West
9.0 out of 10, Wonderful, (29)
"A nice and clean place to come back"
United States
Yudersi S.
The price is ￥15,632
￥43,546 total
includes taxes & fees
Dec 22 - Dec 23
Carey’s Corner | Updated Studio with Heated Pool
Exterior
La Casa de Luna - 1 Bd/1B condo just off upper Duval

La Casa de Luna - 1 Bd/1B condo just off upper Duval

La Casa de Luna - 1 Bd/1B condo just off upper Duval
2.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (103)
"Really enjoyed the unit! The place was a super location just off Duval st but nice and quiet! Had everything you needed for a comfortable stay!"
United States
SALLY L.
La Casa de Luna - 1 Bd/1B condo just off upper Duval
Outdoor dining
THALIA'S RETREAT @ Duval Square 2bd/2ba townhome

THALIA'S RETREAT @ Duval Square 2bd/2ba townhome

THALIA'S RETREAT @ Duval Square 2bd/2ba townhome
2.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (131)
"The place was amazingly clean and in a perfect location!"
United States
LeAnne J.
The price is ￥55,643
￥140,816 total
includes taxes & fees
Dec 21 - Dec 22
THALIA'S RETREAT @ Duval Square 2bd/2ba townhome
Beach
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

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Key West
8.8 out of 10, Excellent, (204)
"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 ￥27,525
￥63,423 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Interior
Retreat to RUM CAY @ Sunrise Suites

Retreat to RUM CAY @ Sunrise Suites

Retreat to RUM CAY @ Sunrise Suites
2.0 star property
Key West
9.6 out of 10, Exceptional, (12)
"Always a good time in Key West. Love this location!"
United States
Gary K.
The price is ￥41,732
￥96,494 total
includes taxes & fees
Dec 24 - Dec 25
Retreat to RUM CAY @ Sunrise Suites
Beach
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (140)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is ￥28,458
￥67,024 total
includes taxes & fees
Dec 21 - Dec 22
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Beach
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK

Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK

Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
Key West
8.8 out of 10, Excellent, (119)
"Good location and value, close enough for a trip downtown"
United States
Christopher R.
The price is ￥26,930
￥64,579 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
Exterior detail
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool
Old Town Key West
9.2 out of 10, Wonderful, (20)
"Great location, clean and quiet"
United States
dennis d.
The price is ￥37,011
￥70,388 total
includes taxes & fees
Dec 22 - Dec 23
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool
Lobby
Two Bedroom Residence

Two Bedroom Residence

Two Bedroom Residence
Key West
9.4 out of 10, Exceptional, (8)
"Incredible place to stay!!"
United States
Jeffrey
The price is ￥60,182
￥109,110 total
includes taxes & fees
Dec 19 - Dec 20
Two Bedroom Residence
TV, offices
The Grand Turk at Sunrise Suites - Pool & Balcony

The Grand Turk at Sunrise Suites - Pool & Balcony

The Grand Turk at Sunrise Suites - Pool & Balcony
Key West
8.4 out of 10, Very Good, (18)
"Perfect fit for our vacation!"
United States
Rhonda H.
The price is ￥47,669
￥102,555 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Grand Turk at Sunrise Suites - Pool & Balcony
Terrace/patio
Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (42)
"This place has everything you need and is in an excellent location. We would definitely stay here again. "
United States
Kimberly D.
The price is ￥47,897
￥103,053 total
includes taxes & fees
Dec 21 - Dec 22
Duval Delight | Recently Remodeled Condo on Duval!
Exterior
Escape to the wonderful Cuban Paradise!

Escape to the wonderful Cuban Paradise!

Escape to the wonderful Cuban Paradise!
2.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (140)
"Would recommend! "
United States
Chelsea B.
The price is ￥54,318
￥127,428 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Escape to the wonderful Cuban Paradise!
Exterior detail
ROYAL 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
9.4 out of 10, Exceptional, (95)
"We really enjoyed the property. "
United States
Shayna
The price is ￥53,184
￥90,915 total
includes taxes & fees
Jan 14 - Jan 15, 2026
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Pool
Duval Street Suites on Duval Free Parking and heated Pool

Duval Street Suites on Duval Free Parking and heated Pool

Duval Street Suites on Duval Free Parking and heated Pool
Old Town Key West
10.0 out of 10, Exceptional, (11)
"Wonderful place! Great location!"
United States
Curtis S.
The price is ￥47,050
￥58,967 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Duval Street Suites on Duval Free Parking and heated Pool
Property grounds
The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.8 out of 10, Excellent, (28)
"This place was amazing! Far enough away from down town yet you could get there in just shy period of time."
United States
Sherry C.
The price is ￥40,122
￥94,610 total
includes taxes & fees
Dec 19 - Dec 20
The Tortuga at Sunrise Suites - Balcony & Pool
TV
Old Town "Eleuthera" • 2BR Waterfront Corner Condo

Old Town "Eleuthera" • 2BR Waterfront Corner Condo

Old Town "Eleuthera" • 2BR Waterfront Corner Condo
Meadows
10.0 out of 10, Exceptional, (28)
"Kim was a huge help and a great host. Great location. "
United States
James C.
The price is ￥73,556
￥135,800 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Old Town "Eleuthera" • 2BR Waterfront Corner Condo
TV
Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
Meadows
9.8 out of 10, Exceptional, (38)
"The condo was nicely cleaned and decorated. Love the huge balcony overlooking the water. "
United States
Trysh W.
The price is ￥73,556
￥135,800 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
Pool
The Grand Cayman | Beautifully Remodeled Key West Condo!

The Grand Cayman | Beautifully Remodeled Key West Condo!

The Grand Cayman | Beautifully Remodeled Key West Condo!
2.0 star property
Key West
The price is ￥27,704
￥70,116 total
includes taxes & fees
Dec 19 - Dec 20
The Grand Cayman | Beautifully Remodeled Key West Condo!
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

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Absolutely loved this resort and everything was perfect. The 2 bedroom villa as beautiful and the screen in deck was perfect! We will definitely be back! Thank you for making our anniversary great!"
Melinda 5-night trip
Posted 20 hours ago
Hyatt Vacation Club at Beach House, Key West

Find out more about Fleming Key

Fleming Key Condo Rentals information

Number of reviews
Accommodation
436 Condo Rentals
Lowest Price
￥203,172
Highest Price
￥203,172

Frequently asked questions

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