Sugarloaf Key, FL Vacation Rentals: house rentals & more

Discover a selection of 1,000 vacation rentals in Sugarloaf Key, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $110 per night, and houses and cottages are popular options for a stay in Sugarloaf Key. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Sugarloaf Key

Search 922 vacation rentals

Stayed Jul 2021

Villa of the setting Sun

Amazing home, seclusion, natural habitat and amazingly responsive customer service to a few small issues with storm related items. Great job Vacasa! We would highly recommend this property and property manager. Thanks Carol at Vacasa, you were so kin...

Stayed Jun 2021

Great Stay on Sugarloaf Key

We spent a week at this rental house in June, 2021. The property was exactly as advertised. The house was comfortable for our family of 5, with fabulous views from every room. As the description indicates, this is not a ‘typical’ beachfront home, i...

Stayed May 2021

Fabulous trip

This is an awesome house and property that's big enough for the whole family and some. 2 master suites so the Grandparents came too. I never saw so much grass in the keys!! Lovely view, had morning deer visitors with our coffee. Close to Key West ...

Stayed May 2021

Fantastic family getaway

A great property to spend a month in the keys. Quiet and private with no one staring into your space during the day or night. The house has fantastic water and sunset views, is very well kept and nicely furnished. With a bath for each bedroom it acco...

Stayed May 2021

May in The Keys

The location of the property was great! The view from the back porch of the water was incredible. We had great access for our 24' boat to the Gulf and Atlantic. The house was very well stocked with all necessities. There is a walking trail along the ...

Stayed Feb 2021

Beautiful property, unbeatable views

Property was excellent, extremely clean, beds very comfortable, well furnished and well equipped! Manager and caretaker were extremely responsive and went the extra mile to be of service. We did get a tide that brought seaweed in but caretaker made s...

Stayed Feb 2021

Excellent Stay!

We enjoyed over a month at Casey and Tom’s place in Sugarloaf. I can’t say enough about the hospitality they provided ahead and during the stay. The home has absolutely everything you’d need, and Casey and Tom were excellent resources for things to d...

Stayed Dec 2020

Beautiful house on Sugarloaf Key

Our family had a lovely stay at this quiet, well maintained home. It is nicer in person than it appears in the photos. We enjoyed beautiful views from the lanai, kayaking in the bay and biking in the neighborhood. We loved how the doors to the lanai ...

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Destination guide

For vacations as sweet as sugar, head to Sugarloaf Key

Sunshine and palm-lined sandy beaches, life in the Florida Keys doesn't get better than this. Sugarloaf Key is a real highlight of the famed Florida Keys. Book a Sugarloaf Key vacation rental in the heart of the island and have some of the best beaches right on your sandy doorstep. Kayaking, swimming and snorkeling are all popular activities. Try a skydiving experience from the small airport, or book a day trip to the Great White Heron National Wildlife Refuge. But if it's just a chilled out vacation you need, then Sugarloaf Key has timeless relaxation written all over it.

Things to do

For uber scuba diving, visit Sugarloaf Key

The Florida Keys are one of the state's most popular diving spots. Located 5 miles offshore from Big Pine Key is the Looe Key National Marine Sanctuary. A popular scuba diving and snorkeling spot, it has the sunken Adolphus Busch shipwreck, which is home to sharks, parrotfish, and barracuda. From your Sugarloaf Key vacation rental, book a scuba diving or snorkeling safari. Back on dry land, don't miss the Bat Tower, one of 14 (now defunct) wooden towers built in 1929 to attract bats to the Keys.

Activities

The Keys to Success - Florida at its best

Life on Sugarloaf Key is all about the beach. Soft coral-white sands lined with swaying palm trees is best for lounging around on with a cocktail in hand. One of the most popular beaches is Sugarloaf Beach on the south of the island. While many come to relax under a radiant sun, there's plenty to keep the water enthusiast occupied. Book a guided sea kayaking tour through the Florida Keys' mangroves, a dolphin-spotting cruise, or a snorkeling safari to see shoals of rainbow-colored fish as they swim just beneath the surface.

Weather

Summertime Blues on Sugarloaf Key

Endless sunshine and blue skies, Sugarloaf Key has certainly been blessed by the weather gods. The Florida Keys' rainy season falls between June and September, when the chance of daily showers increases. The busiest time to visit is spring, between February and May, when the sun is almost always shining and temperatures reach highs of 90 degrees. For the best choice of Sugarloaf Key vacation rentals, come in fall, but beware of high winds as it's the height of hurricane season.

Natural features

A spoonbill of Sugar helps the medicine go down

Blessed with 360-degree views of the Atlantic Ocean, Sugarloaf Key is a U-shaped island in the lower Florida Keys. A short boat trip from Sugarloaf Key is the Great White Heron National Wildlife Refuge. Covering an area of 200,000 acres of open water and islands, visitors can explore the backcountry waters and mangroves, and spot the eponymous heron, brown pelicans, and roseate spoonbills. You can also explore the islands' many protected hiking trails, where you'll see other migratory birds, as well as seasonal wildlife such as deer and nesting sea turtles.

How to get there

How to get to and around Sugarloaf Key

The nearest airport is in Key West, FL (EYW-Key West Intl.), located 14.5 mi (23.4 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Marathon, FL (MTH-Florida Keys Marathon), which is 31.6 mi (50.9 km) away.

How many vacation rentals are available around Sugarloaf Key, FL?

Our 2021 property listings offer a large selection of 922 vacation rentals around Sugarloaf Key. From 603 house rentals to 42 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Sugarloaf Key?

Yes, of course. Vrbo has 603 Houses in Sugarloaf Key. Our other popular types of vacation rentals in Sugarloaf Key include:

Cottages: 42 rentals available
Condos/Apartments: 147 rentals available
Bungalows: 42 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Sugarloaf Key?

Yes, you can select your preferred vacation rental with pool among our 654 vacation rentals with pool available in Sugarloaf Key. Please use our search bar to access the selection of vacation rentals available.