Lower Sugarloaf Key Vacation Rentals from ￥18,688: Search Short-Term Rentals

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Vacation Rentals in Lower Sugarloaf Key

2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

"Great boat cabin. Definitely recommend it. Will visit again. Thanks"

￥37,354 total

includes taxes & fees

Apr 9 - Apr 10

"Unique experience. We loved it!"

￥50,485 total

includes taxes & fees

Apr 9 - Apr 10

"This was an amazing property. Wish we had stayed for more than a night and we're already planning a trip to Key West again just to stay here another time. Very friendly and helpful reception staff. Parking deck is directly across the street. Beautiful pool. Near the water (cruise port), a 5 minute walk to Duval Street, and the Truman Little White House was basically next door. Genuinely cannot say enough good things about this hotel."

￥58,026 total

includes taxes & fees

May 5 - May 6

"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"

"Great property for families. Only downside - if you have a room about be, you can hear everything. So ask for higher rent rates m. Great location, spacious chairs nod and super clean. Loved self cater/clean unit!! "

"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "

"Beautiful place and weather "

￥54,401 total

includes taxes & fees

May 5 - May 6

"This was a perfectly unique and special experience. Matt was amazing to work with for arrival and departure. Timely and exactly as Liam said everything would be. They put special touches on the stay, ice bucket, two waters, beach towels, our name on a cute sign, a cooler, extra covers and everything you need for a Glamping stay on the water! Camping at its best! We definitely plan to come back and will recommend this stay to our friends. This is perfect for outdoor lovers and adventurous people...

￥40,560 total

includes taxes & fees

Apr 9 - Apr 10

"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."

￥46,223 total

includes taxes & fees

Apr 16 - Apr 17

"This was a top notch VRBO! The condo was perfect, with all the needed amentities. Excellent communication with the host, very responsive and helpful. The location was a 4 minute drive from the airport, and all of Key West was easily accessible via walking or the included bicycles. I would highly recommend this host and VRBO to anyone looking for a short getaway, in a great setting. Trust me the pictures don’t do this place justice."

"We enjoyed our stay very much. We stayed in March 2025. The location is nice easy to find, short drive to old town. We spent time at the pool, however, we didn’t realize it wasn’t heated at all, and it was too cold to really enjoy."

￥75,419 total

includes taxes & fees

Apr 16 - Apr 17

"We have traveled to KW every winter for several years. This place is by far the best combination of location and space. Will be back. "

￥72,153 total

includes taxes & fees

Apr 29 - Apr 30

"We loved our 2 nights at Azul. It was quiet, except for THE rooster who crowed from 2:30 am on LOL. White noise was an easy fix so get the app! So cozy, clean, perfect location....really can't say enough! We especially loved the great coffee, water stations, and shared spaces. Would 150% stay again!"

￥43,440 total

includes taxes & fees

Apr 7 - Apr 8

" Comfortable"

￥88,794 total

includes taxes & fees

Apr 9 - Apr 10

"This is really a great space for a couple that enjoys being near the scene but not totally in the middle of the scene. Easy walk to both sides of the island and Duval street. We sat on the front stoop every evening and enjoyed the passersby and traffic. It’s a little noisy from the scooters and golf carts because you are close to the road but it still sleeps comfortably. Nice, cool and dark.Highly recommend using Beth at the concierge service. We had groceries waiting for us and set up a spa day...

"A bit tight for 3 of us, but perfectly set up for a couple. Location is perfect and the pool was a great feature."

￥44,821 total

includes taxes & fees

Apr 8 - Apr 9

"for what we needed, it was fine!"

￥44,029 total

includes taxes & fees

Apr 9 - Apr 10

"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"

￥40,669 total

includes taxes & fees

Apr 9 - Apr 10

"This was a perfect place for us! We traveled with our friends so it was nice to each have our own little space. The rooms are tiny and the bathroom/ shower is even smaller, but the bed was comfy, the location was quiet and perfect. We got in earlier than expected but after some brief text messaging with the contract, she was able to let us in a tax early, which we really appreciated. "

￥83,723 total

includes taxes & fees

Apr 15 - Apr 16

"Great spot. Did the trick! Lovely time and an excellent porch for chilling."

￥49,522 total

includes taxes & fees

Apr 7 - Apr 8

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Other types of properties in Lower Sugarloaf Key you may be interested in

Outdoor pool, pool umbrellas, sun loungers

"Property was great and the food and drinks were great as well"

￥48,682 total

includes taxes & fees

Apr 29 - Apr 30

3 outdoor pools, pool umbrellas, sun loungers

"This hotel is our go to place for Key West. This last trip was excellent as always. "

￥81,972 total

includes taxes & fees

May 5 - May 6

"Stay was great. Staff very nice, helpful. Shuttle to/from airport so convenient. Hotel very close to airport. Shuttle into town and back great as well. Exterior grounds well maintained. Rented 2bd room suite with 1.5 bath. Would be nice if had another shower/tub esp with 5 ppl. Rooms clean, modernized but a bit on small side -doable. Slight damp odor. Cafe and bar fairly good menu choices. Levin the bartender was very nice, made good cocktails. Pool small, crowded. Typical 1st come claim your...

￥56,033 total

includes taxes & fees

May 4 - May 5

Find out more about Lower Sugarloaf Key

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Recent reviews of Lower Sugarloaf Key properties

5/5 Excellent

"This hotel is our go to place for Key West. This last trip was excellent as always. "

A verified traveler stayed at Southernmost Beach Resort

Posted 9 hours ago

The Gates Hotel Key West Newly Renovated

5/5 Excellent

"My family and I loved our stay at The Gates. It was clean and comfortable and for the bill nicely when our departure flight was cancelled. The grounds were beautiful as was the pool. We hit The Blind Pig food truck for dinner and it was amazing! Staff were incredibly pleasant and helpful. We’ll start again for sure."

A verified traveler stayed at The Gates Hotel Key West Newly Renovated

Posted 11 hours ago

Casa Marina Key West, Curio Collection by Hilton

5/5 Excellent

"Beautiful property, well maintained, friendly staff. The room was nice with a small lanai that had a beautiful view. The beds were comfortable and shower was perfect. The bathroom could use more hooks. The breakfast buffet was amazing! There is also a small store. "

A verified traveler stayed at Casa Marina Key West, Curio Collection by Hilton

Posted 2 days ago

5/5 Excellent

"Was upgraded to an absolutely stunning full ocean view room. The room was immaculately clean, the bed was very comfortable to sleep on, bathroom was spacious and clean. We enjoyed the pool and the poolside staff was outstanding. The stay far exceeded my expectations "

A verified traveler stayed at Hyatt Centric Key West Resort and Spa

Posted 2 days ago

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Lower Sugarloaf Key Vacation Rentals

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Vacation Rentals in Lower Sugarloaf Key

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

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

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

Poolside Cottage #411

Poolside Cottage #411

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

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

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

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

The Salt Cay | Updated! Stunning Sunset View, Pool!

The Salt Cay | Updated! Stunning Sunset View, Pool!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Claude Monet Suite | Cozy Studio with Pool & Patio Access!

Claude Monet Suite | Cozy Studio with Pool & Patio Access!

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Other types of properties in Lower Sugarloaf Key you may be interested in

Beachside Resort & Residences

Beachside Resort & Residences

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Margaritaville Beach House Key West

Margaritaville Beach House Key West

Find out more about Lower Sugarloaf Key

Find out more about Lower Sugarloaf Key

Recent reviews of Lower Sugarloaf Key properties

Recent reviews of Lower Sugarloaf Key properties

Southernmost Beach Resort

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Expedia's Latest Trends