Sugarloaf Key Vacation Rentals

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Vacation Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (129)
"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 $190
CA $351 total
includes taxes & fees
Jun 9 - Jun 10
Old Wooden Bridge Resort and Marina
Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (333)
"Ken's place is awesome. Between the included use of two bikes to putt around town, the perfect location (close enough to walk to Duval, but still away from the craziness), the spotless room and bath, ice cold A/C unit, comfy bed, and well apportioned mini kotched...I can't imagine a better deal in Key West. My fiance and I had a blast for our week there. Ken was amazing as well in his communication and helpfulness with the area. Hope we can stay whenever our next trip to KW comes!"
The price is CA $136
CA $327 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (17)
"Clean. Everything we needed in a key west stay."
The price is CA $295
CA $501 total
includes taxes & fees
Jun 12 - Jun 13
Poolside Cottage #411
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Sunshine Key RV Resort & Marina
Sundeck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (130)
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
34’ Catamaran Sailboat
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (88)
"Everyone was extremely nice and helpful."
The price is CA $180
CA $396 total
includes taxes & fees
Jun 11 - Jun 12
Aqua Lodges at Hurricane Hole Marina
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (10)
"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!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, (99)
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is CA $159
CA $374 total
includes taxes & fees
Jun 17 - Jun 18
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Salvador's Studio by Brightwild | Heated Pool!
Pool
Salvador's Studio by Brightwild | Heated Pool!
8.0 out of 10, Very good, (20)
"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 $179
CA $384 total
includes taxes & fees
Jun 17 - Jun 18
Salvador's Studio by Brightwild | Heated Pool!
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (103)
"Beautiful property in a great location. I would definitely stay again."
The price is CA $240
CA $471 total
includes taxes & fees
Jul 7 - Jul 8
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
40'yacht in Paradise Awaits You!
Property grounds
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"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!
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"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 $479
CA $608 total
includes taxes & fees
Jun 18 - Jun 19
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Fridge, microwave, coffee/tea maker, dining tables
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (95)
"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 $175
CA $395 total
includes taxes & fees
Jun 17 - Jun 18
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Beach nearby
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, (56)
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is CA $279
CA $614 total
includes taxes & fees
Jun 10 - Jun 11
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (262)
"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
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Property grounds
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, (214)
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
The Crystalmarine Suite – Rustic Luxury on the Sea
Interior
The Crystalmarine Suite – Rustic Luxury on the Sea
10.0 out of 10, Exceptional, (1)
"This was such a nice and cozy place to spend the weekend! We took our boat from key largo and docked up next to the houseboat and it was just amazing! I live how you can order food delivered to your door! It had tons of privacy and if your wondering no it does not move a lot at night! The solid pannel powered everything at night and we slept very peaceful! The sunsets from this house boat are 2nd to none would stay here again in the future!"
The price is CA $753
CA $943 total
includes taxes & fees
Jun 19 - Jun 20
The Crystalmarine Suite – Rustic Luxury on the Sea
Updated Studio with Heated Pool | Carey's Corner
Pool
Updated Studio with Heated Pool | Carey's Corner
9.6 out of 10, Exceptional, (20)
"Awesome location! The description is accurate and was perfect for the two of us as we explored Key West. Hosts were very responsive. We did not find the neighborhood sketchy as one review described. It was local which, for us, was far more interesting. Great access to everything! Would stay here again!"
The price is CA $197
CA $404 total
includes taxes & fees
Jun 9 - Jun 10
Updated Studio with Heated Pool | Carey's Corner
Key West Beachfront Luxury 2/2 Condo A212
Pool
Key West Beachfront Luxury 2/2 Condo A212
9.8 out of 10, Exceptional, (119)
"Nice property with great furnishings; really liked that it felt more like a residence than a resort. I would stay here again if I had the chance."
Key West Beachfront Luxury 2/2 Condo A212
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Beach nearby
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
9.8 out of 10, Exceptional, (107)
"I recently stayed at Azul Key West, and it was an absolutely incredible experience! The historic charm of the mansion, combined with modern amenities, created the perfect ambiance for a relaxing getaway. The location is unbeatable, just a short walk from Duval Street and the Hemingway House. The serene atmosphere and lush surroundings made it a true oasis. The staff were incredibly welcoming and attentive, ensuring our stay was comfortable and memorable. I highly recommend Azul Key West for...
The price is CA $181
CA $398 total
includes taxes & fees
Jun 12 - Jun 13
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Don't see what you're looking for?
See all available properties in Sugarloaf Key
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.

Sugarloaf Key Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Sugarloaf Key private vacation homes
Known landmarks
Florida Keys Beaches, Sugarloaf Beach and Shark Key
International airports
Miami, FL (MIA-Miami Intl.) and Key West, FL (EYW-Key West Intl.)

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

Sugarloaf Key Hotel at KOA Resort
Private beach, snorkeling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, (165)
"Great location, spacious suite, very clean, would stay here again"
Sugarloaf Key Hotel at KOA Resort
Oceans Edge Key West Resort, Hotel & Marina
6 outdoor pools, free cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1535)
"We enjoy the area, out of the way, yet convenient to most of keys. Relaxing spot and property is always well maintained. Great pool service staff. "
The price is CA $229
CA $337 total
includes taxes & fees
Jun 9 - Jun 10
Oceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1779)
"This is a great place to stay, next time we decide to visit Key West we will fly. This property has shuttle service to and from the airport, they also have shuttle services to the main attraction area, you do not need a vehicle visiting Key West. The beach is directly across the street from the resort " there are not many beach resorts in Key West this one is perfect, The pool area is nice with two tiki bars available, the restaurant has a nice selection of food and it was very good. Hope this...
The price is CA $310
CA $436 total
includes taxes & fees
Jun 9 - Jun 10
Margaritaville Beach House 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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sugarloaf Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sugarloaf Key vacation rentals we have selected for you start as low as CA $136 per night. Entering your travel dates in the search wizard 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. 

Frequently asked questions

Can I find vacation rentals in Sugarloaf Key?

Yes, we offer vacation rentals near popular sights in Sugarloaf Key, or you can go with a secluded option if you want a relaxing place to stay. Our travelers say Sugarloaf Key has a good selection of bars.

What's the top vacation rental in Sugarloaf Key?

Poinciana House in Key West: This vacation home rental outside Sugarloaf Key is located near the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Sugarloaf Key?

Choose from 51 Expedia vacation rentals in Sugarloaf Key for a memorable vacation.

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 vacation rental in Sugarloaf Key like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Sugarloaf Key. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.

Recent reviews of Sugarloaf Key properties
Expedia verified reviews

Ibis Bay Beach Resort

Ibis Bay Beach Resort

5/5 Excellent
"This was a great place, full of history and very unique in its own way. I loved every employee that I came in contact with from the front desk to Greg, the shuttle driver. They felt like family and they all were willing to help in anyway!! Thanks so much!"
A verified traveller stayed at Ibis Bay Beach Resort
Posted 14 hours ago
Ibis Bay Beach Resort