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Compare 814 Vacation Homes in Sugarloaf Key with updated reviews, rates, and availability.

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (190)
"Perfect location, very cute clean place. Would definitely recommend and I will be back"
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (95)
"Had a blast. Great location and accommodation "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

4-11 to 4-16 Special 195 lodg.+ close beach with 4 night stay by

9.0 out of 10, Wonderful, (159)
"The place was cute; we had everything we needed and it was convenient to all the fun w/o being too close to all the noise and busyness of Duval St. Loved it!"
4-11 to 4-16 Special 195 lodg.+ close beach with 4 night stay by

Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen

9.6 out of 10, Exceptional, (214)
"This property is centrally located and we easily biked around to everything. There were restaurants and a gas station in walking distance. The surrounding neighborhood is quiet and neighbors were friendly and quiet. The bed was so comfortable, and the adjustable head of bed was so nice! I feel the price may have been on the high side due to Spring Break. I’d like to stay again and hope the price may be more reasonable in other times of the year.Overall, we loved the place and the location."
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (42)
"We just needed a place for a couple of nights so that we could make the day trip to Dry Tortugas NP. This fit the bill! It wasn’t fancy but we felt safe and were easily able to fit our family of 5. But I wouldn’t have stayed for longer than 2 nights as we would’ve been cramped. We had everything we needed and all the necessary instructions ahead of time. And the view off of the back deck was pretty incredible! Also, if you don’t have a sound machine, be prepared for a rooster alarm clock!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (125)
"Nice spacious property. Comfortable and clean. Plenty of space a great location if you prefer a little more quiet for evenings. Would definitely stay again."
Captain's Daughter: Oversized home for the whole family w/private pool & dock

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

9.6 out of 10, Exceptional, (75)
"I could not suggest anything that could have made this place any better (someone to peel grapes and feed them to me?) really ideal on every front location accommodations cleanliness communication all 10!"
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (179)
"Nothing but great things to say about the house, location and communications with property managers. And what's not to like about having 3 bathrooms, especially with a larger family like ours. Just walk in and start enjoying key west. It's half a block from Duval St. and about a 5 minute walk to Southern Most."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (17)
"Great place that provides easy access to Duval street, is clean with adequate amenities. The property is fully gated and feels very secure. The parking garage "
The price is AED 1,309
AED 3,160 total
includes taxes & fees
9 Apr - 10 Apr
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

9.6 out of 10, Exceptional, (214)
"Wonderful property. Close to everything but also quiet. Had plenty of room for 2 adults and 3 grown children. Would highly recommend it. The heated pool was great! "
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

9.8 out of 10, Exceptional, (182)
"Absolutely a gorgeous property and fantastic location. Key West is our favorite place to visit. This house, along with the property manager, made this year's visit the best yet! Thanks for a great birthday and we look forward to booking this property again next year"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

10.0 out of 10, Exceptional, (13)
"This house was perfect for our couples weekend! Two master king suits with their own private bathrooms. Location was excellent, we were in walking distance to Duval and the marinas. The rental company was great at letting us know about early check in and let us store our bags in their office when needed. There is a grocery store right across the street from the house. "
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (144)
"After reading the other reviews I packed my air mattresses… didn’t need them the beds were fine. The patio rail is fixed based on a previous post. Only 1 working TV but not a big deal. 2 built in ovens but neither works, not ideal for larger family to use a small toaster oven. The place was clean and you can’t beat the location. "
The price is AED 1,102
AED 2,301 total
includes taxes & fees
25 Apr - 26 Apr
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.8 out of 10, Exceptional, (81)
"This was the perfect place for our family to stay. It was very clean and great location. We will be back for sure!"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Perfect Location, Private Heated Pool & Pristine Luxury Home!

10.0 out of 10, Exceptional, (168)
"This home is fully dialed in. Beautiful finishings, all the towels, sunscreen, and pool accessories you could ask for, and a perfect layout with gorgeous private pool and beautifully landscaped backyard space. Would definitely stay here again!"
The price is AED 5,510
AED 9,482 total
includes taxes & fees
13 Apr - 14 Apr
Perfect Location, Private Heated Pool & Pristine Luxury Home!

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (136)
"My sister and friend from north Alabama and my youngest daughter and I decided on a last minute mini vacation. We found this little gem of a place while looking for places to stay in the Keys. Although it could use some TLC, we found the property to be clean, well-stocked and perfect for a short stay, some family time, rest and relaxation. We truly enjoyed our stay and would definitely consider staying here again,"
The price is AED 1,010
AED 2,213 total
includes taxes & fees
20 Apr - 21 Apr
Cudjoe Cottages, swimming pool, just 20 miles from Key West

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

10.0 out of 10, Exceptional, (82)
"As advertised. Everything smooth. Walk anywhere. Thanks for sharing it with us. "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

9.8 out of 10, Exceptional, (146)
"This property is amazingly situated and very well appointed. We have stayed here several times, and it does not disappoint in any respect. The convenience of location (and parking) is amazing and cannot be beat. It's enough off the main street to be comfortably quiet, but you can still enjoy the live music at a level which does not impede conversation while outside. Super clean with high end finishes. The private pool is mostly shaded, which is wonderfully refreshing after being out and about."
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

9.8 out of 10, Exceptional, (86)
"Sam, Charlie and Vic were great"
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (5)
"We stayed for four nights. They have ample beds, a nice tv, a large kitchen, and many parking spots. There are not many walkable beaches but there is a couple of good restaurants nearby. We had a great time, everything was nice, and everything was as listed. I would rent again. "
The price is AED 1,098
AED 2,615 total
includes taxes & fees
10 Apr - 11 Apr
Keys 3 Bedroom Corner Home near Beach & 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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Other property types in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (210)
"I liked the entire experience. The beds were too hard/ firm for me. "
The price is AED 511
AED 942 total
includes taxes & fees
10 Apr - 11 Apr
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (124)
"Unique experience. We loved it!"
The price is AED 426
AED 1,095 total
includes taxes & fees
23 Apr - 24 Apr
Aqua Lodges at Hurricane Hole Marina

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (119)
"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"
Heart of Downtown Key West Cottage With Off-Street Parking
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.