Sugarloaf Key Vacation Rentals from $311: Search Short-Term Rentals

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Our top choices for Sugarloaf Key vacation rentals

Aqua Lodges at Hurricane Hole Marina

Stock Island

Sara

$328 nightly

Feb 26 - Feb 27

Total with taxes and fees

1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

Punta Brisa

Peter

$313 nightly

Feb 10 - Feb 11

Total with taxes and fees

Ocean Front One Bedroom Residence

Key West

$846 nightly

Feb 9 - Feb 10

Total with taxes and fees

Studio, Non Smoking (Tiny House Isla) | Living area | TV, fireplace

Sunshine Key RV Resort & Marina

Big Pine Key

brenda

$305 nightly

Feb 22 - Feb 23

Total with taxes and fees

Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

$975 nightly

Feb 6 - Feb 7

Total with taxes and fees

Contra House Key West

Old Town Key West

$1,535 nightly

Feb 8 - Feb 9

Total with taxes and fees

Island View 1BR Residence With Balcony

Key West

Luis

$642 nightly

Feb 9 - Feb 10

Total with taxes and fees

Ocean Front 2BR Residence

Key West

$1,314 nightly

Feb 9 - Feb 10

Total with taxes and fees

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Top Sugarloaf Key Hotel Reviews

NYAH Key West - Adults Only

10/10 Excellent

"Staff was nice. Room was clean, tho floor in bathroom was a bit wonky. Really liked the pools, met nice ppl from all over during breakfast hours. Close to what we wanted to do. Had to park a couple blocks away. "

Margaritaville Beach House Key West

10/10 Excellent

"This was my favorite hotel during out recent trip to the Keys. I really enjoyed all the little perks they offer like poolside smoothies, cookies and the shuttle. The pool area is very relaxing and fun to hang out at. The rooms were nice including comfortable beds and clean bathrooms. The staff was excellent. I also enjoyed that this hotel is away from all the busy areas on the island and there is a beach across the street."

The Perry Hotel & Marina Key West

10/10 Excellent

"The Perry Hotel was a great experience. Traveled with a friend and stayed in a Mangrove room. Rooms were clean and well cared for. Pool and outside area is clean too. Although outside of downtown, there is a free shuttle that takes you downtown. If you are planning a specific time to go into town, you should ask if the shuttle is typically busy or not. It is first come first serve. Restaurants are great for breakfast or lunch when you arrive. It was a great quiet place to stay with the benefit of being on the water and being able to walk around the docks. Some excursions go out from the marinas as well. "

Parrot Key Hotel & Villas

10/10 Excellent

"The resort staff is friendly and helpful. Amazing they have made a tropical oasis in the midst of a heavy thoroughfare and business area. We enjoyed being a bit away from the busy Duvall and seaport area. Our room (King Suite) had water and garden views. L’Occitane bathroom amenities. Attentive house and grounds keepers. A small table and a sitting chair would have been nice to accommodate playing games. I think some rooms we looked at online do. Only had a couch in living room and bed in the bedroom. We brought in the outdoor seats. The king suites and 2 BR suites (which is a lock off on the 3rd floor) require ascending a flight of stairs, although I did see an elevator that may allow better accessibility. The studios are on the ground floor, but still requires walking up 4-5 stairs. There is a shuttle that we didn’t use to get to the beach and old town. Ride-shares are plentiful. The restaurant, for the one meal we ate there, was overpriced ($30 for a full breakfast), service wasn’t very attentive (eggs were overcooked and waitress never checked to ask for me to send them back. I could have tried to get her attention, but she was too busy talking to another employee…we had to ask another person for our check), and 18% gratuity is automatically added. Denny’s is across the street! Overall it was a great stay, I would highly recommend, and we will definitely stay there again on future travels to Key West (just won’t eat at the restaurant). Thanks fi "

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Everything you need to know about Sugarloaf Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sugarloaf Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sugarloaf Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sugarloaf Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sugarloaf Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sugarloaf Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $311 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sugarloaf Key rentals

At Expedia, we put the best Sugarloaf Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sugarloaf Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sugarloaf Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sugarloaf Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Our top choices for Sugarloaf Key vacation rentals

Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

Ocean Front One Bedroom Residence

Sunshine Key RV Resort & Marina

Atlantic View Luxury Villa with Pool

Contra House Key West

Island View 1BR Residence With Balcony

Ocean Front 2BR Residence

Resort View 2BR Residence

Resort View 3BR Residence

Resort View 1BR Suite With Direct Pool Access

Ocean Front 1BR Suite With Direct Beach Access

Grand Marina Suite by Brightwild Waterfront

Resort View 1BR Suite

New Coastal Rose - Bright Loft With High Ceilings

Two Bedroom Residence With Balcony

Tortuga Suite Sparkling Pool Hot Tub

The Fairhaven House at Solaire Lunara Bay

Mesa House Uno by Brightwild Perfect Location

Poolside Suite by Brightwild Pvt Pool Parking

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Top Sugarloaf Key Hotel Reviews

NYAH Key West - Adults Only

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