Search Condos in Sugarloaf Key

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Sugarloaf Key condo rentals

9.8 out of 10, Exceptional, (110)
"Great value stay"
United States
Mike B.
The price is ¥16,827
¥44,932 total
includes taxes & fees
Dec 17 - Dec 18
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!
9.4 out of 10, Exceptional, (95)
"Location is convenient, about a 15 minute walk go Duval Street so it’s in a nice and quiet area. The pictures are misleading, there is no central AC. "
United States
Priscilla
The price is ¥20,099
¥49,081 total
includes taxes & fees
Dec 17 - Dec 18
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
10.0 out of 10, Exceptional, (2)
"amazing spot close to everything "
United States
Rosalina
The price is ¥52,858
¥80,354 total
includes taxes & fees
Dec 19 - Dec 20
Poolside Suite with Direct Pool Access

Condo in Old Town Key West

Leo’s Lodge | Newly Updated!
8.6 out of 10, Excellent, (21)
"Very nice facility and pool; bathroom was small for large person."
United States
James
The price is ¥15,737
¥43,839 total
includes taxes & fees
Dec 17 - Dec 18
Leo’s Lodge | Newly Updated!
9.2 out of 10, Wonderful, (31)
"4 nights, was perfect"
United States
Ryan M.
The price is ¥34,567
¥86,032 total
includes taxes & fees
Dec 17 - Dec 18
The Barbados at Sunrise Suites - Balcony & Pool

Condo in Old Town Key West

Chagall’s Corner | Newly Remodeled!
9.0 out of 10, Wonderful, (26)
"It was everything we expexted...hoping to stay again only on 1st floor"
United States
Rodney&Roxanne M.
The price is ¥15,656
¥43,614 total
includes taxes & fees
Dec 17 - Dec 18
Chagall’s Corner | Newly Remodeled!
9.6 out of 10, Exceptional, (28)
"2nd time staying here. Love the location and the facilities. Perfect for boating and fishing. The marina is next door so its very convenient. Good times"
United States
robert s.
The price is ¥46,503
¥70,472 total
includes taxes & fees
Dec 17 - Dec 18
Grand Marina Suite - Poolside & Waterfront Condo
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 ¥27,437
¥63,220 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
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 ¥32,564
¥85,736 total
includes taxes & fees
Dec 17 - Dec 18
The Tortuga at Sunrise Suites - Balcony & Pool

Condo in Naval Air Station Key West

The Grenada at Sunrise Suites - Shared Pool
8.6 out of 10, Excellent, (11)
"Great location. Clean. Very nice all around"
United States
Mandie T.
The price is ¥30,847
¥81,537 total
includes taxes & fees
Dec 17 - Dec 18
The Grenada at Sunrise Suites - Shared Pool
9.2 out of 10, Wonderful, (142)
"Really nice location and a beautiful pool. The gym/activities area was not well equipped "
United States
Jennifer H.
The price is ¥170,145
¥273,407 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
The price is ¥25,709
¥67,447 total
includes taxes & fees
Dec 17 - Dec 18
The Grand Cayman | Beautifully Remodeled Key West Condo!
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 ¥28,367
¥66,809 total
includes taxes & fees
Dec 21 - Dec 22
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
9.4 out of 10, Exceptional, (121)
"Good amenities, nice for a weekend get away"
United States
Alexander B.
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
8.4 out of 10, Very Good, (120)
"Resting well and enjoying "
United States
Bon N.
The price is ¥20,255
¥54,968 total
includes taxes & fees
Dec 17 - Dec 18
Dog-friendly resort condo with pool & hot tub, private parking
8.8 out of 10, Excellent, (117)
"We all had a great time and the place was very clean! "
United States
Rebekah A.
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room

Condo in Old Town Key West

Andy’s Attic | Budget-Friendly!
8.4 out of 10, Very Good, (24)
"great location"
United States
Carol
The price is ¥17,051
¥44,392 total
includes taxes & fees
Dec 20 - Dec 21
Andy’s Attic | Budget-Friendly!
9.0 out of 10, Wonderful, (104)
"Very clean and beds are so comfortable. "
United States
Donny G.
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
9.0 out of 10, Wonderful, (31)
"Great place, great location, great communication from host!"
United States
Lara P.
The price is ¥58,904
¥87,407 total
includes taxes & fees
Dec 23 - Dec 24
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
8.6 out of 10, Excellent, (138)
"Everything about the stay was good, my only recommendation would be to put the address for where the fob can be picked up on the initial check in text message to clear any confusion about where the office is located. "
United States
Briana K.
The price is ¥48,828
¥124,124 total
includes taxes & fees
Dec 17 - Dec 18
Comfortable Condo with Pool, Private Balcony, & Beach Access
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 Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Sugarloaf Key Condo Rentals information

Number of reviews
738
Accommodation
395 Condo Rentals
Lowest Price
¥43,614
Highest Price
¥273,407

Frequently asked questions

Why book your condo in Sugarloaf Key with Expedia?
We think that getaways should be stress-free, so if you're seeking condos at a competitive rate, Expedia delivers. Save cash and choose something small and cozy, or splurge on a luxury condo and spoil your favorite people. Our search filters make it easy to find a place in Sugarloaf Key that checks your boxes.
How can I find cheap condos in Sugarloaf Key?
With Expedia's helpful filter tool, getting your hands on cheap condos in Sugarloaf Key is a piece of cake. To find properties that are easy on the wallet, refine your search by star rating, amenities and budget.
What is there to do in Sugarloaf Key near my condo?
The most useful travel accessory is a well-planned to-do list. Florida Keys Beaches is a wonderful place to begin your exploration of Sugarloaf Key.

Explore a world of travel with Expedia