Holiday Homes in Sugarloaf Key

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Featured Holiday Homes in Sugarloaf Key

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

9.0 out of 10, Wonderful, (34)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

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

9.8 out of 10, Exceptional, (63)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
The price is NZ$1,567
includes taxes & fees
2 Feb - 3 Feb
Old Florida Style, wrap around porch, boat basin for dockage, open water

Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach

9.0 out of 10, Wonderful, (156)
"Excellent location very clean. Excellent communication with the owner of the accommodations were wonderful. We enjoyed our New Year’s."
Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach

Poolside Cottage #411

10.0 out of 10, Exceptional, (37)
"From the moment we stepped on the property it was a great experience. We were pleasantly surprised to have a small water view from the front deck of the condo. Walking/biking trail was accessible right outside the property and we could easily walk to a public beach from the property. The condo was well stocked and we had everything we needed to cook our own meals. The resort was quiet and extremely clean. Only disappointment was that “Gumbos” the small bar on property has been closed. Will...
The price is NZ$713
includes taxes & fees
31 Jan - 1 Feb
Poolside Cottage #411

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.6 out of 10, Exceptional, (30)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (39)
"Good place to hang out and relax. Screened in porch and dock we're our favorites. "
Beachside @ Torchview Waterfront Retreat

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

9.6 out of 10, Exceptional, (208)
"We always stay at this location when available. There’s another one at the rear of the property and it was a good spot but we’re spoiled by this one. We’ve stayed here so much it is almost like a second home. It’s well appointed, the shower is huge and the place is cozy and has the lived in feel to it. There’s plenty of basics in the kitchen, full size fridge and stove, the bed is outstanding and adjustable, and there’s even beach chairs to use while staying. Marilyn is a great host and super...
Feb 3-10 $245 off the rates close beach full kitchen & patio

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (175)
"My family enjoyed our stay at Captain’s Quarters. The children especially enjoyed the heated pool and there was adequate room for the seven of us. The bedding was comfortable and it was handy that all of the bedrooms had TVs. There is normally places to park out front if one happens to have a golf cart. There are some issues that need to be addressed and we had many electrical plugs that were very old and wouldn’t work so charging phones became an issue. … It could use a freshen up as window...
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Villa Déjà vu Key West - Steps Off Duval w Private Pool

9.4 out of 10, Exceptional, (54)
"Amazing time and experience! "
Villa Déjà vu Key West - Steps Off Duval w Private Pool

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (63)
"This property was awsome! The area is quiet and close to grocery stores. And a.short drive to down townlpve it, love it, love it. Definitely coming back!!"
Coastal Comfort; Waterfront Luxury Home with private pool!

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

10.0 out of 10, Exceptional, (3)
"Had a wonderful short trip to the keys - this place was in the perfect location to walk all of Key West from shopping Duval street shopping and sight seeing ate lighthouse and even the coast guard station - would highly recommend. "
The price is NZ$2,108
includes taxes & fees
4 Feb - 5 Feb
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

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

9.8 out of 10, Exceptional, (88)
"Beautiful property. Great communication. Very clean. Literally right next to duval street. Highly recommend "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.6 out of 10, Exceptional, (25)
"This property was clean and easy to find. Had to reach out to get access to the property well past the check in time. Minimal kitchen supplies but sufficient. "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (234)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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

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$4,022
includes taxes & fees
23 Feb - 24 Feb
Conch Cove - 3br/3ba with private heated pool and private parking

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

2.0 star property
6.0 out of 10, (2)
"Plenty of room indoors and outdoors to live in. Comfortable beds. Clean and tidy"
The price is NZ$1,880
includes taxes & fees
16 Feb - 17 Feb
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (29)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (200)
"Delighted with the location & size. Quiet but close to activities. Enjoyed the outdoor space- well appointed."
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
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

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (114)
"This was a terrific quick visit, will be back next year for a longer stay. Boat was clean, deck was nice to sit and have a meal or watch the water and the activities. Recommend highly!"
The price is NZ$584
includes taxes & fees
3 Feb - 4 Feb
Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (187)
"Wonderful relaxing stay in a quiet houseboat with all the needed ammenities. Will be back"
The price is NZ$453
includes taxes & fees
3 Feb - 4 Feb
Old Wooden Bridge Resort and Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (289)
"I had a great experience with my family!"
The price is NZ$1,122
includes taxes & fees
2 Mar - 3 Mar
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.