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.
$1,445 nightly
The price is $1,580
Dec 31 - Jan 1, 2026
Total with taxes and fees
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
9.0 out of 10, Wonderful, (11)
"Awesome, would definitely stay again!"
United States
Eugenia C.
$462 nightly
The price is $513
Jan 26 - Jan 27, 2026
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
9.2 out of 10, Wonderful, (31)
"4 nights, was perfect"
United States
Ryan M.
$562 nightly
The price is $624
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Barbados at Sunrise Suites - Balcony & Pool
10.0 out of 10, Exceptional, (24)
"My husband and I stayed at this property for our anniversary week. "
United States
Claudia S.
$550 nightly
The price is $611
Jan 21 - Jan 22, 2026
Total with taxes and fees
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock
8.8 out of 10, Excellent, (205)
"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.
$455 nightly
The price is $507
Jan 15 - Jan 16, 2026
Total with taxes and fees
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
8.8 out of 10, Excellent, (119)
"Good location and value, close enough for a trip downtown"
United States
Christopher R.
$370 nightly
The price is $411
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.
$2,481 nightly
The price is $2,745
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.
$589 nightly
The price is $656
Jan 19 - Jan 20, 2026
Total with taxes and fees
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
9.0 out of 10, Wonderful, (2)
"I had the pleasure of bringing my family down to the keys for their visit. The place was beautifully located and the view is picturesque. The condo itself was easy to check into & truly beautiful. Vaulted ceilings, spacious sleeping quarters and large tub made the stay an exquisite experience. I very much look forward to a future visit & highly recommend."
United States
Luis R.
$1,105 nightly
The price is $1,226
Jan 4 - Jan 5, 2026
Total with taxes and fees
Pool View 3BR Residence | Beachside Resort

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.
$564 nightly
The price is $626
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Grenada at Sunrise Suites - Shared Pool
9.8 out of 10, Exceptional, (110)
"Great value stay"
United States
Mike B.
$432 nightly
The price is $479
Jan 20 - Jan 21, 2026
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!
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.
$666 nightly
The price is $740
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Tortuga at Sunrise Suites - Balcony & Pool
9.0 out of 10, Wonderful, (104)
"Very clean and beds are so comfortable. "
United States
Donny G.
$1,007 nightly
The price is $1,120
Jan 26 - Jan 27, 2026
Total with taxes and fees
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
10.0 out of 10, Exceptional, (34)
"This was such a great condo. We absolutely loved our stay!"
United States
Jennie S.
$1,671 nightly
The price is $1,830
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spectacular Ocean View Amazing quality- Massage Chair. Newly renovated
8.6 out of 10, Excellent, (72)
"Great rental! Perfect for our girls weekend."
United States
Amie W.
$500 nightly
The price is $555
Jan 19 - Jan 20, 2026
Total with taxes and fees
Newly Renovated condo with scenic views, pool & hot tub, balcony, & parking
9.4 out of 10, Exceptional, (95)
"We really enjoyed the property. "
United States
Shayna
$394 nightly
The price is $437
Jan 7 - Jan 8, 2026
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
8.6 out of 10, Excellent, (34)
"Clean, safe, accommodating, great value, good location, special attention when arriving and Transportation, reliable host, great communication, and friendliness."
United States
Nora Lee S.
$429 nightly
The price is $472
Jan 2 - Jan 3, 2026
Total with taxes and fees
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
9.2 out of 10, Wonderful, (21)
"Great location, clean and quiet"
United States
dennis d.
$409 nightly
The price is $454
Jan 12 - Jan 13, 2026
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

Rooftop Penthouse
9.8 out of 10, Exceptional, (50)
"wonderful place!!"
United States
Libby S.
$1,101 nightly
The price is $1,211
Jan 3 - Jan 4, 2026
Total with taxes and fees
Rooftop Penthouse
9.0 out of 10, Wonderful, (31)
"Great place, great location, great communication from host!"
United States
Lara P.
$570 nightly
The price is $632
Jan 4 - Jan 5, 2026
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
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
692
Accommodation
364 Condo Rentals
Lowest Price
$411
Highest Price
$2,745

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?
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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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