Holiday Homes in Sugarloaf Key

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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Featured Holiday Homes in Sugarloaf Key

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, (210)
"Great location. The room met our needs. It was clean and comfortable. The owner did a great job of communicating everything we needed to know. Everything was walkable, which we appreciated. "
Feb 3-10 $245 off the rates close beach full kitchen & patio
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
Terrace/patio

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

9.0 out of 10, Wonderful, (157)
"The good: convenient location, quiet, bed was comfortable, the little patio in the back is nice. The bad: there is no “on site’ parking but we always found parking on the street about a block away, The communication with property manager was a bit strange, she accused us of still being inside the unit a full day after we had check out on time, despite texting her to tell her we had left (an hour before check out)"
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
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, (188)
"This was a great property. Nice and quiet. Gated for privacy. Would use again and will recommend. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
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!

9.8 out of 10, Exceptional, (75)
"Located 1 block away from Duval Street. Property Manager answered our few questions almost immediately. We enjoyed the pool and ease of checking in and out. Centrally located by everything. I would recommend if you need 3 bedrooms downtown. Off street parking for one car is also included. "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
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, (4)
"Great location, right in the middle keys, easy access to everything. "
The price is NZ$1,367
includes taxes & fees
9 Mar - 10 Mar
Keys 3 Bedroom Corner Home near Beach & Key West
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, (122)
"Our stay was absolutely incredible. The condo was bigger than we were expecting so we had plenty of room to spread out and relax. The property management website was super helpful and the customer service was amazing as well! Nothing but good reviews from everyone who stayed there!"
Captain's Daughter: Oversized home for the whole family w/private pool & dock
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!

9.6 out of 10, Exceptional, (209)
"The property was conveniently located just off of Duval street near the Southernmost point. We were able to walk everywhere. There were a lot of nearby restaurants for breakfast (and other meals, but we always ate breakfast out). The house was clean and just how described. We had everything we needed. We enjoyed the heated pool and waterfall. The water pressure was a bit lacking in the bathroom, but that wasn’t a deal breaker. We enjoyed our stay, and would recommend it. "
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
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, (10)
"This was the perfect spot to walk to most places in old town! The beds were very comfortable and the rooms were spacious. We loved being able to enjoy the quiet back yard and pool. There is a resident rooster who does a great job of patrolling the parking lot and may be an alarm clock for some. We did have a hiccup with checking in- we were provided the wrong code and it took a few times to get ahold of the host. But the host was always very friendly and helpful. We also found small bugs...
The price is NZ$2,402
includes taxes & fees
6 Apr - 7 Apr
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
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, (90)
"Clean, roomy, comfortable. Adequate seating and dishes for 6 adults. Great mattresses and pillows. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
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, (133)
"Three employees traveling in the Keys stayed and all reported their complete satisfaction with the accommodations and location. Thank you!"
The price is NZ$1,096
includes taxes & fees
13 Mar - 14 Mar
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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!

9.8 out of 10, Exceptional, (66)
"The house is roomy with a nice pool for kids. It is quite close to Duval Street, but far enough away to avoid the noise."
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Conch Cove - 3br/3ba with private heated pool and private parking
A heated pool

Conch Cove - 3br/3ba with private heated pool and private parking

10.0 out of 10, Exceptional, (4)
"Rick and team were awesome and exceptional throughout the whole stay! Nice house!! "
The price is NZ$3,024
includes taxes & fees
18 Mar - 19 Mar
Conch Cove - 3br/3ba with private heated pool and private parking
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, (7)
"Richard was great, place was clean and great location! Would come again for sure!"
The price is NZ$1,805
includes taxes & fees
8 Mar - 9 Mar
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
Tropical Key West out of the way
Pool

Tropical Key West out of the way

9.4 out of 10, Exceptional, (159)
"We very much enjoyed our stay here Location was perfect. We were able to ridecour bikes into Key West easily. Each bedroom having a private bathroom was a bonus. "
Tropical Key West out of the way
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
Marina

Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!

9.8 out of 10, Exceptional, (119)
"My husband and I stayed at this lovely three-story home with two other couples. The home is well furnished and well stocked and immaculate. We thoroughly enjoyed the outdoor deck and pool area for cocktails, playing cards or just relaxing. We would definitely stay again!"
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
The Flower Power House - Boho Beautiful
A heated pool

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (25)
"We truly enjoyed our stay at the Flower Power House! The house was awesome, in a great neighborhood and had everything we needed! The property manager was very pleasant, responsive and accommodating! We will definitely return the next time we are in Key West! Thank you! "
The Flower Power House - Boho Beautiful
3-bedroom townhome in Key West with fitness room, WiFi
Smart TV

3-bedroom townhome in Key West with fitness room, WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
"The home was very clean and well-appointed. Hosts were very responsive."
3-bedroom townhome in Key West with fitness room, WiFi
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very good, (85)
"This house is beautiful, it’s an old Keys style home, nautical, clean, beautiful views, we spent most of our time in the pool. Great place to just get away and relax. Love that is was off the beaten path. The palm trees, coconuts and yard is beautiful. The owner answered us almost immediately for any needs or questions we had. Will definitely make this a yearly trip. "
Private Secluded Ocean View & Pool Near Key West
Luxury two floor apartment in prime location of famous Duval Street
Beach towels

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (75)
"We loved the location and style of this apartment. Perfect for small families or couples. "
The price is NZ$1,471
includes taxes & fees
1 Apr - 2 Apr
Luxury two floor apartment in prime location of famous Duval Street
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Outdoor pool, a heated pool

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

9.8 out of 10, Exceptional, (221)
"2nd year staying at this property will boook again. 5 start accomodations and location"
The price is NZ$3,760
includes taxes & fees
27 Mar - 28 Mar
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
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
8.4 out of 10, Very good, (195)
"Everything about it was great"
The price is NZ$526
includes taxes & fees
10 Mar - 11 Mar
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (121)
"We enjoyed the small deck that allowed us to watch the boat activity. The shower was so slick it was dangerous to use. It was a little inconvenient to either walk on the short gravel path or walk on the decking and step over all the hoses that were used by the fishing boats. Overall, it was about what we expected from the web site description."
The price is NZ$697
includes taxes & fees
12 Mar - 13 Mar
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (375)
"Thank you"
Steps from Duval, Pool on Site & Bikes Included!
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.