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, (171)
"Loved everything, will return"
The price is AU$394
includes taxes & fees
5 Jan - 6 Jan 2025
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (106)
"Nice for affordable price "
The price is AU$599
includes taxes & fees
8 Jan - 9 Jan 2025
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (359)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is AU$514
includes taxes & fees
9 Jan - 10 Jan 2025
Steps from Duval, Pool on Site & Bikes Included!

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is AU$851
includes taxes & fees
8 Jan - 9 Jan 2025
Poolside Cottage #411

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (29)
"The property was great and the host was very responsive to communication. "
34’ Catamaran Sailboat

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!

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

8.8 out of 10, Excellent, (204)
"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 AU$638
includes taxes & fees
2 Jan - 3 Jan 2025
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

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

9.4 out of 10, Exceptional, (109)
"Easy location and overall peaceful neighborhood. Surprisingly peaceful for how close it is to main roads"
The price is AU$692
includes taxes & fees
4 Jan - 5 Jan 2025
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

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

9.0 out of 10, Wonderful, (32)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

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

9.4 out of 10, Exceptional, (115)
"The property was great and as advertised. Overall location was very good in terms of proximity to Duval St, museums etc. Truman st can get very busy but ended up not being an issue. Would recommend the Inn to friends. "
The price is AU$665
includes taxes & fees
2 Jan - 3 Jan 2025
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

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

9.6 out of 10, Exceptional, (172)
"We stayed at Riptides this last week. Centrally located, this efficient unit is nestled right into the neighborhood just a few streets off of Duvall. It is still very quiet while close to action. Check in and communication with our host Whitney was great! Comfy bed, little kitchen and easy stay. It lived up to the positive ratings!"
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

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

9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
The price is AU$1,164
includes taxes & fees
7 Jan - 8 Jan 2025
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

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

9.8 out of 10, Exceptional, (219)
"Perfect location with sunset views and kayaking "
The price is AU$1,211
includes taxes & fees
26 Jan - 27 Jan 2025
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

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 AU$1,425
includes taxes & fees
4 Jan - 5 Jan 2025
The Crystalmarine Suite – Rustic Luxury on the Sea

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

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 AU$1,008
includes taxes & fees
11 Jan - 12 Jan 2025
The Caroline Suite | 1 bed, 1 bath condo w/shared pool

Bahama Village studio @ the Galleria!

9.6 out of 10, Exceptional, (10)
"The property was great. It was nice and quiet, close proximity to everything. We enjoyed our stay. The kitchen are came very nicely equipped. "
Bahama Village studio @ the Galleria!

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

CORONA ~ Adults Only, King Suite with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (132)
"I love staying at Azul, Corona fits my lifestyle perfectly. The property is located within walking distance of my interests. The property is always neat and clean. I will choose this property again in the future. "
The price is AU$842
includes taxes & fees
4 Jan - 5 Jan 2025
CORONA ~ Adults Only, King Suite with Community Pool at Azul Mansion!

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

9.8 out of 10, Exceptional, (278)
"Beautiful. Tastefully decorated top floor condo in great location. Close to Smathers beach. Bikeable to Old Town. Included bicycles are a nice touch. Gorgeous pool and grounds. Would definitely return. Fun stay"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
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, (275)
"Can't wait to go back..!"
Sugarloaf Key Hotel at KOA Resort

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
8.8 out of 10, Excellent, (1539)
"We celebrated 28 years of marriage here and it was everything we hoped for. The view of the ocean was beautiful, the people were friendly and kind, and amenities exceeded our expectations."
The price is AU$613
includes taxes & fees
26 Jan - 27 Jan 2025
Oceans Edge Key West Resort, Hotel & Marina

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2204)
"Southernmost was great from the renovated rooms/baths to the staff who were all SO accommodating! The pools are nice, it is lovely to have restaurant/bars on site! A great experience!"
The price is AU$791
includes taxes & fees
12 Jan - 13 Jan 2025
Southernmost 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.