Sugarloaf Key Vacation Rentals

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Vacation Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (259)
"I love this place!!!"
The price is ¥11,611
¥34,324 total
includes taxes & fees
Oct 13 - Oct 14
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (164)
"The stay was beautiful "
The price is ¥12,528
¥39,437 total
includes taxes & fees
Oct 14 - Oct 15
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, (314)
"Great hotel with excellent location "
The price is ¥36,398
¥46,052 total
includes taxes & fees
Oct 30 - Oct 31
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (405)
"this was exactly as advertised and close to all the action"
The price is ¥13,471
¥33,791 total
includes taxes & fees
Oct 13 - Oct 14
Steps from Duval, Pool on Site & Bikes Included!

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

6.6 out of 10, (12)
"Unfortunately this stay was very disappointing. The marina was awesome. Tessa was awesome. The boat itself was disgusting. The pictures are very deceiving. What you see is not what you get. "
The price is ¥24,546
¥50,105 total
includes taxes & fees
Oct 15 - Oct 16
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (23)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is ¥24,795
¥64,638 total
includes taxes & fees
Oct 27 - Oct 28
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (819)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (82)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
The price is ¥52,917
¥114,451 total
includes taxes & fees
Nov 8 - Nov 9
Old Florida Style, wrap around porch, boat basin for dockage, open water

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (138)
"Great Location, Free Parking, comfortable beds"
Heart of Downtown Key West Cottage With Off-Street Parking

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

8.8 out of 10, Excellent, (232)
"Property was cute and in a great location! "
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

Island View 1BR Residence With Balcony

2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
The price is ¥32,619
¥49,554 total
includes taxes & fees
Nov 3 - Nov 4
Island View 1BR Residence With Balcony

Comfortable Condo with Pool, Private Balcony, & Beach Access

8.6 out of 10, Excellent, (135)
"Nice area, location, and wonderful apartment!"
The price is ¥26,609
¥89,741 total
includes taxes & fees
Oct 26 - Oct 27
Comfortable Condo with Pool, Private Balcony, & Beach Access

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (183)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

7.8 out of 10, Good, (22)
"Loved everything about the stay, "
The price is ¥37,798
¥74,840 total
includes taxes & fees
Oct 13 - Oct 14
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

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

9.8 out of 10, Exceptional, (46)
"Wonderful view, lot's of space, great location "
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Resort View 1BR Suite

2.0 star property
9.0 out of 10, Wonderful, (4)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
The price is ¥31,684
¥48,503 total
includes taxes & fees
Oct 13 - Oct 14
Resort View 1BR Suite

Living the Dream Key West Style

9.8 out of 10, Exceptional, (26)
"Great hosts and great accommodations!"
The price is ¥40,685
¥49,552 total
includes taxes & fees
Oct 13 - Oct 14
Living the Dream Key West Style

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

9.8 out of 10, Exceptional, (24)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location and very nice room"
The price is ¥12,095
¥45,150 total
includes taxes & fees
Oct 15 - Oct 16
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (190)
"Bucket list trip. Great location. Property was just what was expected. Perfect for 2!"
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

10.0 out of 10, Exceptional, (191)
"Outstanding place to stay, centrally located!"
The price is ¥136,071
¥276,924 total
includes taxes & fees
Oct 14 - Oct 15
Perfect Location, Private Heated Pool, Pristine Luxury Home!
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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Top Sugarloaf Key Hotel Reviews

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