Sugarloaf Key Holiday Rentals

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Holiday Rentals in Sugarloaf Key

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (1)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
Private and Exclusive Beach Getaway

The Lighthouse - Beach Houses Key West

9.6 out of 10, Exceptional, (11)
"We saved up for 3 years for this trip and this property did not disappoint! Thank you for sharing your beautiful piece of paradise with us!"
The price is AU$2,562
includes taxes & fees
7 July - 8 July
The Lighthouse - Beach Houses Key West

The Hemingway - Beach Houses Key West

9.8 out of 10, Exceptional, (7)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
The price is AU$2,645
includes taxes & fees
30 July - 31 July
The Hemingway - Beach Houses Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

The price is AU$1,145
includes taxes & fees
14 July - 15 July
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (8)
"Great location, right in the middle keys, easy access to everything. "
The price is AU$969
includes taxes & fees
10 July - 11 July
Keys 3 Bedroom Corner Home near Beach & Key West

🌴 TROPICAL RETREAT 🌴 RV in the Keys

The price is AU$504
includes taxes & fees
13 July - 14 July
🌴 TROPICAL RETREAT 🌴 RV in the Keys

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

9.6 out of 10, Exceptional, (75)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is AU$1,363
includes taxes & fees
2 Aug - 3 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water

One of the very few beach houses with a daily, rental license in the Keys.

8.8 out of 10, Excellent, (62)
"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"
The price is AU$2,136
includes taxes & fees
18 July - 19 July
One of the very few beach houses with a daily, rental license in the Keys.

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (117)
"This was our second time staying here. Feels very secluded although it's right off the highway. We saw many Key deer on our way to No Name Pub , including babies who thougt we should feed them) (We did not feed them). Highly recommend!"
The price is AU$794
includes taxes & fees
19 July - 20 July
Kelly's Kabin - Adorable Private Summerland Key Cottage

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Venture Out is a gated community in Cudjoe Key. The house was very clean and had everything you need to make yourself comfortable. We visited Key West which is about 30 minutes by car. Great place to stay"
The price is AU$1,413
includes taxes & fees
10 July - 11 July
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
9.4 out of 10, Exceptional, (3)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
The price is AU$1,311
includes taxes & fees
12 July - 13 July
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Post Card Point #319 - Ocean Views!

10.0 out of 10, Exceptional, (47)
"Really nice super clean & modern house with a great view. Lots of space. The community it’s in was very nice and quiet."
The price is AU$1,279
includes taxes & fees
19 July - 20 July
Post Card Point #319 - Ocean Views!

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (94)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is AU$821
includes taxes & fees
28 July - 29 July
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.4 out of 10, Exceptional, (3)
"The Blue Lobster is a gem. Clean, cute, enough room to spread out and every extra provided to make your stay comfortable. Community is friendly and has a nice pool, hot tubs and pickle ball courts. Loved it here. "
The price is AU$947
includes taxes & fees
6 July - 7 July
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (18)
"This is our second time staying at this property and everything was just as good as the first time!"
The price is AU$1,051
includes taxes & fees
15 July - 16 July
Spanish Queen @Venture Out, Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (80)
"Great atmosphere, right on a canal. A perfect and comfortable home!"
The price is AU$764
includes taxes & fees
6 July - 7 July
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (5)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is AU$946
includes taxes & fees
13 July - 14 July
Island Time #110 Ocean Views - Cudjoe Key

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

7.8 out of 10, Good, (12)
"Good experience. The property is well place and the Venture is really nice and quiet."
The price is AU$793
includes taxes & fees
10 July - 11 July
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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

9.8 out of 10, Exceptional, (235)
"We (family of 5) really enjoyed our stay. All the equipment was as listed and in great condition. The location was perfect if you're looking for a less hectic Florida Keys experience."
The price is AU$1,330
includes taxes & fees
6 July - 7 July
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock
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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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.