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Compare 338 Condo Rentals in Sugarloaf Key with updated reviews, rates, and availability.

Coconut Mallory Resort And Marina By Kees Vacations
2 outdoor pools
Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
8.2 out of 10, Very Good, (789)
"Great property on the water at the Marina . 2 salt water swimming pools and a nice hot tub . Best to rent bikes and go the Stock Island for lunch or dinner. Also can rent kayaks at Stock Island. "
Coconut Mallory Resort And Marina By Kees Vacations
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
Beach nearby
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
9.4 out of 10, Exceptional, (88)
"We had a wonderful time! Thoroughly enjoyed the pool every day! Perfect temp and no kids! We will be back for sure! "
The price is $118
per night
Jun 13 - Jun 14
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
THE GOOD LIFE ~ Charming 1 Bedroom, 1 Bath Truman Annex Condo!
Property grounds
THE GOOD LIFE ~ Charming 1 Bedroom, 1 Bath Truman Annex Condo!
10.0 out of 10, Exceptional, (17)
"The condo was very small, but fine for two people. The kitchen and bath were updated and very nice. Carpeting needs to go away. And the furnishings are in bad need of updating. We loved the balcony. It was so spacious. The bed was very comfortable. Headboard is the wrong size. Our property manager, Melanie, was so helpful and was quick to return our calls. Thank you! We love the Truman Annex and always stay there. This was our first time in the Shipyard Condos. We enjoyed it very much."
THE GOOD LIFE ~ Charming 1 Bedroom, 1 Bath Truman Annex Condo!
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FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (103)
"Beautiful property in a great location. I would definitely stay again."
The price is $127
per night
Jun 16 - Jun 17
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Beach nearby
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, (56)
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is $204
per night
Jun 10 - Jun 11
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
Pool
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
9.8 out of 10, Exceptional, (136)
"Appreciated the amenities."
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
Tranquility by Smathers and 10 minute bike downtown Key West value savings
A heated pool
Tranquility by Smathers and 10 minute bike downtown Key West value savings
9.4 out of 10, Exceptional, (95)
"Room was clean, had lots of items that were paid forward like coffee, filters, cooking spray. Also has two beach chairs, sand play kit, and towels. My best advice is to take bug spray for the mosquitos…sadly, they ruined the trip for us."
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pool | Outdoor pool, a heated pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (262)
"Very clean and well decorated and equipped. The owners are very helpful with anything that comes up. The pool is huge, and the ocean is right behind it providing your own little beach. Very relaxing. Would definitely stay here again."
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
NEW YEAR - NEW CRAZY LOW DEALS ON FANTASTIC HOME
Exterior
NEW YEAR - NEW CRAZY LOW DEALS ON FANTASTIC HOME
9.4 out of 10, Exceptional, (174)
"We love staying in the Shipyard and find it a fantastic location. This property was the best unit we’ve stayed in. Very clean and comfortable with awesome decor. One room is a little tight with the queen bed taking up most of the room but the bed and bedding were very comfortable so it was easy to forget. Highly recommended."
NEW YEAR - NEW CRAZY LOW DEALS ON FANTASTIC HOME
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
A heated pool
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
9.2 out of 10, Wonderful, (74)
"Relax"
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Botanical Island Delight Key West fantastic discounts for Summer & Fall
A heated pool
Botanical Island Delight Key West fantastic discounts for Summer & Fall
9.0 out of 10, Wonderful, (112)
"The location was wonderful and quiet. Great pool and views while at the pool. Nice garden view from the room. Easy drive to Duval Street and other attractions. The biggest downside is the very dated and worn furnishings."
Botanical Island Delight Key West fantastic discounts for Summer & Fall
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
A heated pool
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
9.2 out of 10, Wonderful, (146)
"We had a wonderful week. The condo was clean and comfortable. We enjoyed the pool and ocean view! Condo had everything we needed and exceeded our expectations. Location was quiet but easy to access Old Town Key West via Uber. Would definitely recommend!"
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
THE SWEET LIFE ~ Charming 2 BR/1 Ba Condo w/ Community Pool!
Property grounds
THE SWEET LIFE ~ Charming 2 BR/1 Ba Condo w/ Community Pool!
9.8 out of 10, Exceptional, (9)
"We rented the Condo at Shipyard because of the walkability factor. It was cozy and sufficient for a 1 week stay. It was clean and nicely decorated. We came to Key West to purchase a house, which we did, so we are now on our way to becoming Freshwater Conch's. I texted with Melanie and communication with her was great. So nice! I did use the pool at Shipyard which was nice. This is a two bedroom with queen beds and one bath so great for a family for a relaxing vacay! Thanks Melanie... It will be...
THE SWEET LIFE ~ Charming 2 BR/1 Ba Condo w/ Community Pool!
SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!
Property grounds
SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!
10.0 out of 10, Exceptional, (34)
"Everything was perfect. the house & location. Exactly where we wanted to be. Anything you are looking for is just a walk away."
SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, (99)
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is $123
per night
Jun 18 - Jun 19
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Fridge, microwave, coffee/tea maker, dining tables
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (95)
"Wonderful stay. Was not in the room much, except to sleep and used the pool and common areas a few times and, overall, Azul was just beautiful and should I return, I would stay here again."
The price is $124
per night
Jun 16 - Jun 17
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Beach nearby
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
9.8 out of 10, Exceptional, (108)
"My wife and I stayed for a long weekend (Thurs - Sunday) and we had a great time. We will definitely stay again and highly recommend this location. If you are going, rent a golf cart as it is much easier to get around."
The price is $128
per night
Jun 12 - Jun 13
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Penthouse Level Ocean Views- Live the Dream
Outdoor pool, a heated pool
Penthouse Level Ocean Views- Live the Dream
9.6 out of 10, Exceptional, (210)
"We really enjoyed our stay. This was a great rental property. Views were amazing."
Penthouse Level Ocean Views- Live the Dream
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
A heated pool
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
10.0 out of 10, Exceptional, (55)
"Great location, clean, and quiet neighborhood close to everything"
The price is $179
per night
Jun 8 - Jun 9
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
CLARO ~ Adults Only, Poolview 1 BR, 1 Ba Suite in Azul Mansion!
Beach nearby
CLARO ~ Adults Only, Poolview 1 BR, 1 Ba Suite in Azul Mansion!
9.8 out of 10, Exceptional, (110)
"We had an amazing stay. The room was clean and comfy and the pool was a great feature to have to cool off during the day in between doing things around the island. The only suggestion I have is maybe black out curtains or maybe leave eye masks in the rooms because they are very bright with light due to the very lit outside hallways at night (which I liked for safety) but definitely kept us up at night and as soon as the sun came up, it was all daylight. Thank you for the great stay! We will be...
The price is $116
per night
Jun 9 - Jun 10
CLARO ~ Adults Only, Poolview 1 BR, 1 Ba Suite in Azul Mansion!
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See all available properties in Sugarloaf Key
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.

Other property types in Sugarloaf Key

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV
Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, 129 reviews
"So,keep in mind that we were just stopping over for the night and thought it be fun to stay the night on a houseboat with the kids on our way to the next part of our trip. We did not realize that this was a fishing area and found it very smelly! Now, if you are an avid fisherman or fisherwoman, then you probably wouldn’t have a problem with it. The place was fine, I would say it’s more like camping in an RV. We enjoy seeing the key deer and iguana…it was the highlight of our stay."
The price is $139
$256 total
includes taxes & fees
Jun 9 - Jun 10
Old Wooden Bridge Resort and Marina
Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 333 reviews
"Ken's place is awesome. Between the included use of two bikes to putt around town, the perfect location (close enough to walk to Duval, but still away from the craziness), the spotless room and bath, ice cold A/C unit, comfy bed, and well apportioned mini kotched...I can't imagine a better deal in Key West. My fiance and I had a blast for our week there. Ken was amazing as well in his communication and helpfulness with the area. Hope we can stay whenever our next trip to KW comes!"
The price is $99
$239 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, 88 reviews
"Everyone was extremely nice and helpful."
The price is $98
$251 total
includes taxes & fees
Jun 12 - Jun 13
Aqua Lodges at Hurricane Hole Marina
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.

Sugarloaf Key Condo Rentals information

Number of reviews
2,175
Accommodation
338 Condo Rentals
Lowest Price
$116
Highest Price
$204

Frequently asked questions

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Recent reviews of Sugarloaf Key hotels
Expedia verified reviews

Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

5/5 Excellent
"Great management and great staff"
A verified traveler stayed at Fairfield Inn and Suites by Marriott Key West
Posted 18 hours ago
Fairfield Inn and Suites by Marriott Key West