Lower Sugarloaf Key Vacation Rentals

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Vacation Rentals in Lower Sugarloaf Key

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, 127 reviews
"So,keep in mind that we were just stopping over for the night and thought it be fun to stay the night on a houseboat with the kids on our way to the next part of our trip. We did not realize that this was a fishing area and found it very smelly! Now, if you are an avid fisherman or fisherwoman, then you probably wouldn’t have a problem with it. The place was fine, I would say it’s more like camping in an RV. We enjoy seeing the key deer and iguana…it was the highlight of our stay."
The price is CA $189
CA $349 total
includes taxes & fees
Jun 3 - Jun 4
Old Wooden Bridge Resort and Marina
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 331 reviews
"Beautiful studio and great location. Communication with the owner was excellent."
The price is CA $149
CA $342 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Poolside Cottage #411
10.0 out of 10, Exceptional, 17 reviews
"Clean. Everything we needed in a key west stay."
The price is CA $294
CA $494 total
includes taxes & fees
Jun 4 - Jun 5
Poolside Cottage #411
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34’ Catamaran Sailboat
9.4 out of 10, Exceptional, 25 reviews
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, 10 reviews
"The Yacht was beautiful. The marina was amazing. The marina and resort had excellent restaurants and bars. It was very cool to see all of the boats coming and going. It was an easy Uber ride to Key West and enjoy the fast pace life. Then it was wonderful to come back to the quiet of the marina. Would highly recommend a stay here."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, 88 reviews
"Everyone was extremely nice and helpful."
Aqua Lodges at Hurricane Hole Marina
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, 258 reviews
"We really enjoyed our stay at this property. The condo was clean and well supplied with essentials. The property is well maintained and safe. We were able to use the included bicycles to get to most locations we wanted to go in old town. Southernmost point was a leisurely 15 min bike ride away. The property owner communicated well with us and answered all of our questions. The only thing we were not prepared for was the traffic noise. The unit does face a busy street, so you can hear vehicles...
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, 229 reviews
"Great open communication with the property owner! Property located in quaint area of key west nearest Ram’s head restaurant, and the world famous blue heaven!!"
The price is CA $407
CA $790 total
includes taxes & fees
Jun 3 - Jun 4
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, 99 reviews
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is CA $158
CA $369 total
includes taxes & fees
Jun 3 - Jun 4
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, 94 reviews
"Wonderful stay. Was not in the room much, except to sleep and used the pool and common areas a few times and, overall, Azul was just beautiful and should I return, I would stay here again."
The price is CA $159
CA $371 total
includes taxes & fees
Jun 3 - Jun 4
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, 103 reviews
"Beautiful property in a great location. I would definitely stay again."
The price is CA $188
CA $408 total
includes taxes & fees
Jun 16 - Jun 17
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Salvador's Studio by Brightwild | Heated Pool!
8.0 out of 10, Very good, 20 reviews
"So enjoyed it ! Had never stayed in this part of Old Town , and this introduced me to so much. Would absolutely return."
The price is CA $176
CA $375 total
includes taxes & fees
Jun 3 - Jun 4
Salvador's Studio by Brightwild | Heated Pool!
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, 192 reviews
"This house was great. We had an amazing time. No complaints at all. It was walking distance to all the fun places. It was equipped with everything you need and the pool was an added plus. Cant say enough good things about it. The owner was also great to work with. We loved it!"
The price is CA $816
CA $1,896 total
includes taxes & fees
Jun 5 - Jun 6
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, 201 reviews
"We stayed in cabin 6 for a week. Management was very helpful. The cabin had everything we needed. Very comfortable bed and the 2 baths were definitely a plus. Great location. Within walking distance to everything. We did rent a golf cart and parking was never a problem. We are planning our next trip and will stay here again."
The price is CA $296
CA $698 total
includes taxes & fees
Jun 24 - Jun 25
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, 23 reviews
"We had a really nice couple of days on this boat. We are older (over 60), and we weren't sure if it was going to be our thing. It was good though! The host was amazingly helpful. We loved the private beach and pool right around the corner. We have been to Key West a lot, so we didn't need to do all the tourist stuff. We mostly stayed on Stock Island. It was easy to get Ubers, so we didn't bother with a car or golf cart. If we were staying longer, we probably would have rented a golf cart. The...
40'yacht in Paradise Awaits You!
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, 56 reviews
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is CA $278
CA $608 total
includes taxes & fees
Jun 10 - Jun 11
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
9.2 out of 10, Wonderful, 109 reviews
"My husband and I visit Key West every year. We don’t go to frequent Duval Street we go for the warmth of the sun, artist fairs, sunsets, our favorite restaurants and our favorite shops. My husband does go fishing with the guys once or twice. But we come back and feel as though we’ve been in paradise. When your husband is a farmer it does really seem like paradise 😂"
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, 18 reviews
"Good location as far walking distance to a Cuban food truck- Luna. Hogfish is a good restaurant, good seafood and good service, short walk. Property was clean. Beds comfortable. Mostly quiet. It’s about 3 miles from Key West."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, 214 reviews
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, 204 reviews
"Beautiful and quiet location. Close to Key West yet just far enough to be away from the crowds. Family thoroughly enjoyed it. Everything is as pictured and immaculately clean, truly a gem. Melanie was friendly, always available and always responsive."
The price is CA $477
CA $602 total
includes taxes & fees
Jun 18 - Jun 19
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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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.

Lower Sugarloaf Key Vacation Rental Travel Info

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

Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, 1,521 reviews
"The hotel was great!!! The staff was great. The property is on stock island and set back away from busy streets yet close to everything. Downtown key west was 5 minutes away. We rented a scooter and drove everywhere on that."
The price is CA $228
CA $336 total
includes taxes & fees
Jun 4 - Jun 5
Oceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, 1,773 reviews
"Great place to stay "
The price is CA $312
CA $437 total
includes taxes & fees
Jun 6 - Jun 7
Margaritaville Beach House Key West
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, 1,476 reviews
"We had a wonderful stay! The front desk, tiki bar, and pool were great!"
The price is CA $217
CA $331 total
includes taxes & fees
Jun 24 - Jun 25
Havana Cabana at Key West
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lower Sugarloaf Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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