Holiday Homes in Sugarloaf Key

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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Featured Holiday Homes in Sugarloaf Key

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

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!
A heated pool

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
Terrace/patio

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
Feb 3-10 $245 off the rates close beach full kitchen & patio
Exterior detail

Feb 3-10 $245 off the rates close beach full kitchen & patio

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."
Feb 3-10 $245 off the rates close beach full kitchen & patio
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

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
A heated pool

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

9.8 out of 10, Exceptional, (126)
"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!
A heated pool

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

9.6 out of 10, Exceptional, (76)
"We loved staying at this house! Truly an oasis in Key West - privacy, pool and pool setting was awesome, easy to walk to everything Key West has to offer! Everything was clean, comfortable and equipped with everything we needed. Can't wait to go back!"
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Fridge, microwave, oven, stovetop

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
A heated pool

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

10.0 out of 10, Exceptional, (18)
"The property was as described. The location was perfect and quiet. We'd love to the pool and hanging out there. Customer service was outstanding."
The price is NZ$1,492
includes taxes & fees
14 Apr - 15 Apr
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
A heated pool

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

9.8 out of 10, Exceptional, (216)
"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!
A heated pool

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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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 NZ$1,090
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!
A heated pool

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!
Outdoor pool, a 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 NZ$4,490
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
Outdoor dining

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

8.8 out of 10, Excellent, (137)
"Nice location. Comfortable place although the couch and living room chair were old and stained. "
The price is NZ$1,048
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!
A heated pool

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

10.0 out of 10, Exceptional, (82)
"Location. Location. Location. One block off Duval St and near everything. We rented a car but didn’t need it. Walked everywhere. "
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
Outdoor dining

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…
Beach

**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
Fridge, microwave, oven, stovetop

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 NZ$1,347
includes taxes & fees
7 May - 8 May
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 Bedroom Aqua Lodge # 13 Barracuda | Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (211)
"Good experience, clean house and safe !"
The price is NZ$446
includes taxes & fees
13 Apr - 14 Apr
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (126)
"Absolutely loved this property. Very affordable, cozy and good quality stays. Be ready for a little fish smell when walking outside! But I did not mind that. "
The price is NZ$519
includes taxes & fees
20 Apr - 21 Apr
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (292)
"This was an amazing property. Wish we had stayed for more than a night and we're already planning a trip to Key West again just to stay here another time. Very friendly and helpful reception staff. Parking deck is directly across the street. Beautiful pool. Near the water (cruise port), a 5 minute walk to Duval Street, and the Truman Little White House was basically next door. Genuinely cannot say enough good things about this hotel."
The price is NZ$639
includes taxes & fees
17 Apr - 18 Apr
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.