Search and Rent Sugarloaf Key Condos

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Our top choices for Sugarloaf Key condo rentals

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.
$1,678 nightly
The price is $1,838
Dec 31 - Jan 1, 2026
Total with taxes and fees
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
8.6 out of 10, Excellent, (141)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
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.
$370 nightly
The price is $411
Jan 11 - Jan 12, 2026
Total with taxes and fees
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
8.4 out of 10, Very Good, (18)
"Perfect fit for our vacation!"
United States
Rhonda H.
$534 nightly
The price is $593
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Grand Turk at Sunrise Suites - Pool & Balcony
9.0 out of 10, Wonderful, (11)
"Awesome, would definitely stay again!"
United States
Eugenia C.
$623 nightly
The price is $691
Jan 8 - Jan 9, 2026
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
9.6 out of 10, Exceptional, (98)
"Very clean and private. We enjoyed our time and would return."
United States
Janine W.
$468 nightly
The price is $519
Jan 13 - Jan 14, 2026
Total with taxes and fees
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
9.0 out of 10, Wonderful, (138)
"Great stay"
United States
Jason U.
$580 nightly
The price is $644
Jan 17 - Jan 18, 2026
Total with taxes and fees
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
9.0 out of 10, Wonderful, (29)
"A nice and clean place to come back"
United States
Yudersi S.
$351 nightly
The price is $387
Dec 23 - Dec 24
Total with taxes and fees
Carey’s Corner | Updated Studio with Heated Pool
8.8 out of 10, Excellent, (119)
"Good location and value, close enough for a trip downtown"
United States
Christopher R.
$366 nightly
The price is $406
Jan 11 - Jan 12, 2026
Total with taxes and fees
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK

Condo in Old Town Key West

The Lighthouse Group Suite
2.5 star property
8.0 out of 10, Very Good, (2)
"Clean, great location, and cute pool"
United States
Kerrie D.
$2,589 nightly
The price is $2,853
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Lighthouse Group Suite
9.4 out of 10, Exceptional, (121)
"Good amenities, nice for a weekend get away"
United States
Alexander B.
$583 nightly
The price is $650
Jan 19 - Jan 20, 2026
Total with taxes and fees
Sunny Condo with WiFi, Hot Tub, Pool & Tennis

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.
$566 nightly
The price is $628
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Grenada at Sunrise Suites - Shared Pool
9.0 out of 10, Wonderful, (31)
"Great place, great location, great communication from host!"
United States
Lara P.
$507 nightly
The price is $564
Dec 23 - Dec 24
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
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.
$644 nightly
The price is $717
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Tortuga at Sunrise Suites - Balcony & Pool
10.0 out of 10, Exceptional, (34)
"This was such a great condo. We absolutely loved our stay!"
United States
Jennie S.
$1,956 nightly
The price is $2,145
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spectacular Ocean View Amazing quality- Massage Chair. Newly renovated
9.0 out of 10, Wonderful, (104)
"Very clean and beds are so comfortable. "
United States
Donny G.
$913 nightly
The price is $1,013
Dec 24 - Dec 25
Total with taxes and fees
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
10.0 out of 10, Exceptional, (2)
"amazing spot close to everything "
United States
Rosalina
$522 nightly
The price is $580
Jan 4 - Jan 5, 2026
Total with taxes and fees
Poolside Suite with Direct Pool Access
9.4 out of 10, Exceptional, (95)
"We really enjoyed the property. "
United States
Shayna
$410 nightly
The price is $455
Jan 8 - Jan 9, 2026
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
9.2 out of 10, Wonderful, (20)
"Great location, clean and quiet"
United States
dennis d.
$292 nightly
The price is $324
Dec 23 - Dec 24
Total with taxes and fees
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated 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.
$490 nightly
The price is $539
Jan 5 - Jan 6, 2026
Total with taxes and fees
Chagall’s Corner | Newly Remodeled!
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 Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Sugarloaf Key Condo Rentals information

Number of reviews
700
Accommodation
364 Condo Rentals
Lowest Price
$324
Highest Price
$2,853

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.

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