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Compare 419 Condo Rentals in Sugarloaf Key with updated reviews, rates, and availability.

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
Coconut Mallory Resort And Marina By Kees Vacations

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (130)
"The location is so close of downtown and Duvall St. The room is little but charmingThe little swimming pool is clean There are a minimum of little thingsCoffee tea by a machine and fresh water by a fountain linen and towels have never changed!!!No cleaning!!!It’s not normal for the price!!!"
The price is $297
includes taxes & fees
$268 per night
May 5 - May 6
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!

9.2 out of 10, Wonderful, (7)
"Recommend a key pad for the front door. We were on the first floor next to the front door with no lock. "
The price is $297
includes taxes & fees
$268 per night
May 5 - May 6
THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (173)
"This is really a great space for a couple that enjoys being near the scene but not totally in the middle of the scene. Easy walk to both sides of the island and Duval street. We sat on the front stoop every evening and enjoyed the passersby and traffic. It’s a little noisy from the scooters and golf carts because you are close to the road but it still sleeps comfortably. Nice, cool and dark.Highly recommend using Beth at the concierge service. We had groceries waiting for us and set up a spa day...
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!

9.4 out of 10, Exceptional, (107)
"Azul mansion is in a great location with easy walking to Duval, Higgs Beach, etc. Free parking that was always available onsite. Very clean. Bathroom could use an update. If staying in Ambrosia, note that the light and sounds take some getting used to. You have the light from the pool area (we were fine with it but if you are sensitive to light this is not the room for you) and the ceiling fan and air conditioning unit are fairly loud. The first night we were awake every hour but it got better....
The price is $360
includes taxes & fees
$324 per night
May 8 - May 9
AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!

STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!

9.8 out of 10, Exceptional, (88)
"My family of 6 loved this place. The location was close to the ferry which was how we arrived on the island so that started everything off on the right foot. We very much appreciated the central location of the house. It was an easy walk to the piers, Mallory Square, Duval Street, and all the restaurants and shops you could want. But, it was off the main drags so you didn't get a lot of night time noise and disturbance. The best of both worlds. The house has a great patio for night time...
STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

9.2 out of 10, Wonderful, (130)
"Overall we enjoyed our stay. Positive highlights: the pool including southern exposure, large dining table, and comfortable beds. Not shown in pictures is a larger TV (50" ?), a new glasstop range, and coffee maker which can both make a pot and accepts KCups. The unit was nicely furnished with kitchen supplies (cups, plates, pans, measuring cups etc).Negatives insights: a LOT of no see ums, pool area could use more umbrellas (get there by mid-morning), a broken living room chair (wobbles; needs...
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!

9.4 out of 10, Exceptional, (8)
"Great property in a great location out of the craziness of Duval but still close enough to enjoy. "
The price is $359
includes taxes & fees
$324 per night
May 5 - May 6
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

9.8 out of 10, Exceptional, (81)
"This is a 10 out of 10 property. Absolutely beautiful room. Comfortable bed. Exquisitely decorated. AC to the max. The pool was a fabulous 90! We loved it! "
The price is $391
includes taxes & fees
$352 per night
May 5 - May 6
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

8.6 out of 10, Excellent, (11)
"Great sleepy part of town to get away from all the hustle and bustle of Duval. "
The price is $387
includes taxes & fees
$351 per night
May 14 - May 15
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!

9.8 out of 10, Exceptional, (124)
"Very good spot to stay. Easy to walk to everything in Old Key West. Thanks "
The price is $314
includes taxes & fees
$283 per night
May 6 - May 7
FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!

Leo’s Lodge | Newly Updated!

8.2 out of 10, Very Good, (11)
"It was a nice clean place smarter than I thought, but it gave us what we needed. "
The price is $332
includes taxes & fees
$302 per night
May 8 - May 9
Leo’s Lodge | Newly Updated!

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (105)
"Excellent location, walkable to Duval Street. We were able to park on-site and walk to everything. We would definitely stay here again."
The price is $292
includes taxes & fees
$263 per night
May 4 - May 5
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

9.4 out of 10, Exceptional, (79)
"good place to stay. Walls between rooms thin"
The price is $400
includes taxes & fees
$360 per night
May 21 - May 22
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.

9.8 out of 10, Exceptional, (7)
"The place was great - had most everything we needed. Location was ideal across the street from the beach. Pool and tennis court were both great. "
Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (286)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Key West Beachfront Luxury 2/2 Condo A212

10.0 out of 10, Exceptional, (146)
"Third time at this address. Never disappoints"
Key West Beachfront Luxury 2/2 Condo A212

SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!

9.8 out of 10, Exceptional, (78)
"Very happy with location — close enough to Duval but far enough for more quiet. We were able to walk to nearly all restaurants, beach, and other attractions. Check-in was easy, communication ahead of stay was clear, place was clean & had everything a traveler needs to feel at home."
The price is $447
includes taxes & fees
$402 per night
May 1 - May 2
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!

ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath

9.8 out of 10, Exceptional, (45)
"Loved the location and ease of getting everywhere we needed downtown! Everything on the inside was very clean and more upscale than several VBROs we have stayed at. The only thing that would have helped is in the instructions mention that you can easily walk down the alley to the right as walk out the front door (near the Italian/pizza place). Walked down the block to the left twice before I realized there was a quicker way. "
The price is $927
includes taxes & fees
$835 per night
May 6 - May 7
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath

Luxury Waterfront at Galion Resort in Old Town

9.6 out of 10, Exceptional, (80)
"It was a great time but I must apologize for some in my group. Had I known that they were going to be so loud and unruly. I would not have brought them. They will never go another trip with me. So for everyone that had been bothered by them I apologize once more. group. "
The price is $855
includes taxes & fees
$771 per night
May 4 - May 5
Luxury Waterfront at Galion Resort in Old Town
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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Other property types in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (223)
"The only thing i didn't like was my short time there! I wish i would've booked more nights, this place is incredible. Great location, beautiful scenery, friendly helpful staff"
The price is $256
includes taxes & fees
$239 per night
May 1 - May 2
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (134)
"Loved every minute of our stay!!! We wish that we would have booked a longer stay. Next time we definitely will!!!"
The price is $329
includes taxes & fees
$292 per night
May 6 - May 7
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (295)
"We had a nice stay. The property was in a great location."
The price is $343
includes taxes & fees
$305 per night
May 4 - May 5
Hyatt Vacation Club at Sunset Harbor, Key West
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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