Holiday Rentals in Sugarloaf Key

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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, (176)
"Unique hotel with early communication from the owners. Definitely not a quiet location as we heard lots of loud marina-related boat noises all night. A great place to sleep with ear plugs. The shower was quite small and challenging to warm (like an RV shower). All showers were lukewarm. Also, there are very limited dining options nearby, so vacationers to the keys who are not cooking their meals on-site daily will likely be driving to Key West (30 miles away) a good deal of their time here."
The price is €238
includes taxes & fees
26 Jan - 27 Jan
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (112)
"We loved staying on the houseboat."
The price is €303
includes taxes & fees
20 Jan - 21 Jan
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
The price is €341
includes taxes & fees
3 Feb - 4 Feb
Steps from Duval, Pool on Site & Bikes Included!

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "
34’ Catamaran Sailboat

Poolside Cottage #411

10.0 out of 10, Exceptional, (35)
"Great little condo - perfect for our family to visit Key West! "
The price is €402
includes taxes & fees
31 Jan - 1 Feb
Poolside Cottage #411

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (169)
"Quaint little (actually spacious) cottage on waterfront. Easy access and enough off the beaten path where your solitude isnt interrupted. Gorgeous sunrise view. It was nice to have in-house washer/dryer. My only suggestion would be to add an outlet plug with USB ports. Bang for buck it was well worth it!"
Direct Oceanfront Cottage-Sunrise View- #2,

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

9.8 out of 10, Exceptional, (16)
"Staying on the Grand Admiral was really awesome for my wife and I. The location at Perry Marina was exceptional. The whole process was very easy, working with Kathy for booking, Stephanie for check-in and Captain John for our charter, everything went smooth. "
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

9.6 out of 10, Exceptional, (118)
"We had a great time. Enjoyed the property very much."
The price is €651
includes taxes & fees
10 Feb - 11 Feb
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

9.4 out of 10, Exceptional, (111)
"Great location!"
The price is €433
includes taxes & fees
24 Jan - 25 Jan
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

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

8.8 out of 10, Excellent, (205)
"I recently stayed at this property and had a generally pleasant experience. The property itself is nice and well-maintained, with a great location that adds to its appeal. The surrounding area is excellent, making it convenient and enjoyable. However, there were a few downsides to my stay. The internet was not working, which was quite inconvenient. Additionally, while the property is good overall, it could benefit from having a few more amenities. The bathroom, in particular, could use some...
The price is €867
includes taxes & fees
14 Feb - 15 Feb
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

The Caroline Suite | 1 bed, 1 bath condo w/shared pool

9.4 out of 10, Exceptional, (12)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
The price is €688
includes taxes & fees
26 Jan - 27 Jan
The Caroline Suite | 1 bed, 1 bath condo w/shared pool

The Crystalmarine Suite – Rustic Luxury on the Sea

10.0 out of 10, Exceptional, (2)
"This VRBO is a dream for those looking to escape the hustle and bustle of everyday life. With its unique location, it provides a perfect blend of adventure and relaxation. Whether you're looking to reconnect with nature or simply unwind in a beautiful setting, this floating house offers an unparalleled experience."
The price is €884
includes taxes & fees
21 Jan - 22 Jan
The Crystalmarine Suite – Rustic Luxury on the Sea

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

9.4 out of 10, Exceptional, (215)
"Very clean. Could use some updating such as fresh paint. "
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

9.6 out of 10, Exceptional, (82)
"Great trip with 16 people for a 50th birthday party. Host was very helpful and informative throughout the trip. Great for large groups."
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

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

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (220)
"Our family loved everything about our stay in Cudjoe Key. The property had everything we needed and was extremely comfortable. The property owner was very friendly and helpful and easy to get a hold of. We highly recommend this place for your next vacation!"
The price is €747
includes taxes & fees
20 Jan - 21 Jan
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Bahama Village studio @ the Galleria!

9.6 out of 10, Exceptional, (10)
"Everything was as advertised. Its location was fantastic with easy access on foot to everything Key West has to offer. Only negative is that there is a high top table and two chairs in a space that really doesn’t afford those niceties. The bed was comfortable. The ac was a bit loud."
The price is €415
includes taxes & fees
20 Jan - 21 Jan
Bahama Village studio @ the Galleria!

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (280)
"We had a wonderful week during the Christmas/ New Year break. The condo is exceptional. Very clean including many items that make your stay easy and welcoming. The kitchen is fully stocked, not that one needs much while staying on the island. We relaxed in the condo, enjoyed restaurants and music across the island. "
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Luxury 62' Yacht! In a Beautiful Resort

10.0 out of 10, Exceptional, (7)
"Excellent boat, excellent stay. Would love to return."
Luxury 62' Yacht! In a Beautiful Resort

Unique Home with loft @ Truman Annex

9.8 out of 10, Exceptional, (113)
"Not a single issue, very responsive"
Unique Home with loft @ Truman Annex
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, (288)
"The place was very clean and friendly!!! The dog park was stinky, but there is grassy areas outside the front of the park. The suits were beautiful and very spacious!"
Sugarloaf Key Hotel at KOA Resort

Havana Cabana at Key West - Adults Only

4.0 star property
8.8 out of 10, Excellent, (1647)
"Cute place with friendly staff and tropical vibes. "
The price is €304
includes taxes & fees
20 Jan - 21 Jan
Havana Cabana at Key West - Adults Only

Ibis Bay Beach Resort

2.5 star property
8.0 out of 10, Very good, (1713)
"The room was incredibly small, but I don't mind that, since it makes it easier for the ac to cool the room. I would appreciate a check-in more ar 2pm or even 3pm than 4pm and the breakfast started at 6am instead of 8am."
The price is €332
includes taxes & fees
20 Jan - 21 Jan
Ibis Bay Beach Resort
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.