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Featured Condo Rentals in Sugarloaf Key and around

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

9.0 out of 10, Wonderful, (16)
"Great accommodations. Perfect location."
The price is €270
includes taxes & fees
22 Jun - 23 Jun
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (814)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

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

9.8 out of 10, Exceptional, (114)
"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 €210
includes taxes & fees
23 Jun - 24 Jun
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

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

9.6 out of 10, Exceptional, (136)
"We had a great 2 night stay while in Key West. The property was as advertised.The FREE off-street parking was an excellent perk.The location was very good as it was within walking distance of the heart of Key West."
The price is €207
includes taxes & fees
23 Jun - 24 Jun
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!

9.4 out of 10, Exceptional, (173)
"Really enjoyed the place, very clean and comfortable, great balcony overlooking the ocean. The amenities like the pool and hot tub were very nice and it's a short bike / drive / Lyft from everything in Key West. "
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!

THE WHITEHEAD ROOM @ The Inn on Fleming ~ 2nd Floor Queen w/ Shared Pool!

9.0 out of 10, Wonderful, (10)
"Great time staying there "
The price is €218
includes taxes & fees
23 Jun - 24 Jun
THE WHITEHEAD ROOM @ The Inn on Fleming ~ 2nd Floor Queen w/ Shared Pool!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (177)
"We would definitely stay here again! Great location, exactly as described, overall great place."
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

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

8.8 out of 10, Excellent, (18)
"Property as described in listing, enjoyed our stay! Would def stay again! "
The price is €226
includes taxes & fees
23 Jun - 24 Jun
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

Duval Delight | Recently Remodeled Condo on Duval!

9.8 out of 10, Exceptional, (21)
"The unit is awesome - perfect location on Duval St, very comfortable beds, plenty of space. Will definitely be back!"
The price is €445
includes taxes & fees
1 Jul - 2 Jul
Duval Delight | Recently Remodeled Condo on Duval!

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

9.6 out of 10, Exceptional, (86)
"Nice Property. Would stay again."
The price is €236
includes taxes & fees
22 Jun - 23 Jun
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

THE TRUMAN ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (15)
"Great place"
The price is €220
includes taxes & fees
30 Jun - 1 Jul
THE TRUMAN ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w/ Shared Pool!

BOOKING SMOKING HOT 2025 DEALS NOW!

9.4 out of 10, Exceptional, (200)
"wonderful place to stay"
BOOKING SMOKING HOT 2025 DEALS NOW!

CORTEZ ~ Adults Only, Poolview King Room at Azul Mansion!

9.6 out of 10, Exceptional, (130)
"The property was near all the points of interest. We walked everywhere and got our steps in."
The price is €207
includes taxes & fees
25 Jun - 26 Jun
CORTEZ ~ Adults Only, Poolview King Room at Azul Mansion!

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

9.8 out of 10, Exceptional, (40)
"Property was well maintained and nice folks in the community. Recommend highly!"
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

COCONUT PALM STUDIO ~ Adult Only Studio, Heated Shared Pool & Close to Town!

9.6 out of 10, Exceptional, (82)
"Great stay, clean property in a perfect location that is quiet and still walkable. Would gladly stay here again!"
The price is €254
includes taxes & fees
29 Jun - 30 Jun
COCONUT PALM STUDIO ~ Adult Only Studio, Heated Shared Pool & Close to Town!

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

8.8 out of 10, Excellent, (16)
"Great location and a lovely restored home. The common area was fabulous, with a full kitchen, eating/gathering area, and a small plunge pool. Room was nice but needed a few repairs. Bathroom vanity was worn and needs replacing. The appearance of some small bugs was disturbing but quickly addressed. Overall a nice place to stay. "
The price is €220
includes taxes & fees
29 Jun - 30 Jun
THE FLAGLER ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!

JULIE ~ Adult Only, 1st Floor King Bedroom w/ Shared Pool, Scarlet Mango Inn!

10.0 out of 10, Exceptional, (70)
"Very lush and beautiful. We loved the location of area and of our room, the Julie. Very private and pool right outside our door. Everything we needed was there. Parlor was lovely and nice place to hang other than your room. Front porch with rocking chairs were the cherry on top. Lovely vacation stay. "
The price is €283
includes taxes & fees
26 Jun - 27 Jun
JULIE ~ Adult Only, 1st Floor King Bedroom w/ Shared Pool, Scarlet Mango Inn!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (135)
"The property was exactly as listed. Great location, well kept, clean, and easy to check into. I don’t even know how I’d improve upon the experience, it was great. Parking on site was great as well! "
The price is €211
includes taxes & fees
24 Jun - 25 Jun
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Leo’s Lodge | Newly Updated!

8.6 out of 10, Excellent, (13)
"Bery mice pkace clean and quiet close to Duvall street"
The price is €226
includes taxes & fees
25 Jun - 26 Jun
Leo’s Lodge | Newly Updated!

ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

9.6 out of 10, Exceptional, (127)
"Great place to stay. Clean, great location. "
The price is €280
includes taxes & fees
22 Jul - 23 Jul
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
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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