Sugarloaf Key Holiday Rentals

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Holiday Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (189)
"Nice quiet area Everyone is so friendly and the little deer , are just adorable "
The price is AU$410
includes taxes & fees
6 Feb - 7 Feb
Old Wooden Bridge Resort and Marina

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 AU$503
includes taxes & fees
9 Feb - 10 Feb
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, (289)
"I had a great experience with my family!"
The price is AU$671
includes taxes & fees
6 Feb - 7 Feb
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (803)
"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."
Coconut Mallory Resort And Marina By Kees Vacations

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

10.0 out of 10, Exceptional, (2)
"Owner communication was great and Master Suite was very comfortable. AC worked great, boat has lot of bathroom space! Our charter to see the sunset was spectacular with such a great kind crew that did a professional job. Our stay overall was verand will book again on our next trip"
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (365)
"Nice, clean and roomy studio. Very customer-oriented management. Perfect location for attending all the various festival venues. "
The price is AU$544
includes taxes & fees
6 Mar - 7 Mar
Steps from Duval, Pool on Site & Bikes Included!

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is AU$843
includes taxes & fees
3 Mar - 4 Mar
Poolside Cottage #411

PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

9.6 out of 10, Exceptional, (14)
"Great location good layout but outdated and for the price paid should be more up to date. The bed was very uncomfortable and the pillows were subpar but the interaction with the management was amazing"
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (17)
"Rented this nice boat for 2 nights for a two 60-somethings and three 20-somethings. From "A to Z" it meet or exceeded our expectations. Boat was a bit old, the carpets, etc. were more that a bit "dingy", and 5 adults certainly "maxed out" the space.... but we didn't care much. It was such a unique experience for our 3 younger guests who had NEVER been on a boat before. The harbor is very nice with good restaurants. etc. Jim our "check-in /out" guy was great. Jeff our captain for our 4 hour boat...
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

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

9.8 out of 10, Exceptional, (64)
"Clean well equipped great location"
The price is AU$1,434
includes taxes & fees
9 Feb - 10 Feb
Old Florida Style, wrap around porch, boat basin for dockage, open water

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

9.8 out of 10, Exceptional, (117)
"This has been our go to place to stay while in the keys. We love the pool, hot tub and beach. My boys can walk right out into the beach and start fishing. It is out of the hustle and bustle but not too far out. Highly recommend!"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (216)
"Very clean. Could use some updating such as fresh paint. "
The price is AU$1,163
includes taxes & fees
24 Feb - 25 Feb
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Margarita Cottage ~ Popular island retreat

2.0 star property
9.6 out of 10, Exceptional, (37)
"Loved our stay at the Margarita Cottage. Walked all over Key West from very central location. Heated Pool was a plus - even for a mid December dip!"
The price is AU$1,125
includes taxes & fees
19 Feb - 20 Feb
Margarita Cottage ~ Popular island retreat

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

9.0 out of 10, Wonderful, (34)
"Great place in a very convenient location! Pull out couch isn’t the most comfortable thing in the world, but it sleeps. Super clean, super easy check in (was even able to get in early) and a great price! "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

9.4 out of 10, Exceptional, (108)
"Nice, comfortable, clean, walkable to Duval Street & other places."
The price is AU$1,078
includes taxes & fees
4 Mar - 5 Mar
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point & Shared Pool!

8.8 out of 10, Excellent, (249)
"The accommodation is quaint and bathroom is a challenge but room was very clean. Location is surrounded by local residences. Pool was very peaceful and felt great. Close to historic locations by easy walk. "
J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point & Shared Pool!

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

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (2)
"We used our paddle boards to get back to the docks to uber around town. We also were able to pick up a pizza at the ocean wall! It was an amazing way to visit Key West! Very peaceful! Great Location! Definite ocean front! Can’t get any closer! Wonderful experience! Absolutely would do it again! "
The price is AU$443
includes taxes & fees
1 Mar - 2 Mar
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Spec.Feb.24-Mar 1 @275 lodg + 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 @275 lodg + w. 3 night stay close beach

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (31)
"Great time enjoying the keys like a pirate. "
34’ Catamaran Sailboat
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 types of properties in Sugarloaf Key you may be interested in

Sugarloaf Key Hotel at KOA Resort

3.0 star property
9.8 out of 10, Exceptional, (297)
"Our room was spacious, clean, and had a beautiful balcony overlooking the marina and water. Pool area was clean with plenty of deck space and seating options away from the water. Cafe/bar offered good selection of food. Campground employees made regular rounds at pool area to check on guests. We enjoyed trivia night, as well as the live music offered at the bar area. "
Sugarloaf Key Hotel at KOA Resort

Ibis Bay Beach Resort

2.5 star property
8.0 out of 10, Very good, (1751)
"Was very nice and clean. Close to everything.."
The price is AU$556
includes taxes & fees
6 Feb - 7 Feb
Ibis Bay Beach Resort

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1005)
"Very nice."
The price is AU$737
includes taxes & fees
6 Feb - 7 Feb
The Perry Hotel & Marina 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.

Frequently asked questions

Can I find holiday rentals in Sugarloaf Key?

Yes, there are holiday rentals close to the most popular sights in Sugarloaf Key, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Sugarloaf Key has a good selection of bars.

What are some of the best holiday rentals that Sugarloaf Key has to offer?

Poinciana House in Key West: This holiday home rental outside Sugarloaf Key is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Sugarloaf Key?

Choose from 51 Expedia holiday rentals in Sugarloaf Key for a memorable holiday.

What’s there to see and do in Sugarloaf Key?

Florida Keys Beaches and Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Upper Sugarloaf Key and Saddlebunch Keys.

What’s a holiday rental in Sugarloaf Key like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sugarloaf Key. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.