Sugarloaf Key Holiday Rentals

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Holiday Rentals in Sugarloaf Key

2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (123)
"Amazing stay in a boat!"
The price is NZ$412
includes taxes & fees
27 May - 28 May
Old Wooden Bridge Resort and Marina
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is NZ$392
includes taxes & fees
30 May - 31 May
Steps from Duval, Pool & Bikes $129-$299 Night!
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
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Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is NZ$603
includes taxes & fees
28 May - 29 May
Poolside Cottage #411
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
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!
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (86)
"It’s an experience, it’s not a luxury stay. It’s sort of like staying in a camper with a septic holding tank that can get pretty smelly next to a working marina, with fish charters and a fish cleaning station. One morning we had to use a spare paddle to shoe away a stinky dead fish head so it wouldn’t get trapped under our unit and smell up the place. Staying on the water was unique but in mid May it would have been nice for more shade on the little deck. I’d save it for the slightly cooler...
The price is NZ$504
includes taxes & fees
27 May - 28 May
Aqua Lodges at Hurricane Hole Marina
Pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (258)
"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
Sun-loungers, beach towels
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, (228)
"Description and pictures accurate. Clean, got what you need, quick response to my questions. Great for me and my husband in a room. Bikes were awesome to have. Couple blocks off Duval. Each room is good for two. Enjoyed the stay!"
The price is NZ$952
includes taxes & fees
3 Jun - 4 Jun
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, (98)
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is NZ$444
includes taxes & fees
27 May - 28 May
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Fridge, microwave, coffee/tea maker, dining tables
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (93)
"We stayed for a long weekend and really enjoyed the Fontana Room at Azul Mansion. We were able to park on-site and check-in was very easy. It was walking distance to everything: Smathers Beach, the Southernmost Point, and Mallory Square. The pool was nice, and the amenities were great: fresh, cold water always available; Kuerig and pods in the room; plenty of towels including pool towels. Only downside was the pool lights shown into the room at night so room darkening curtains would be good. We...
The price is NZ$488
includes taxes & fees
11 Jun - 12 Jun
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (102)
"Beautiful property in a great location. I would definitely stay again."
The price is NZ$459
includes taxes & fees
29 May - 30 May
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
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 NZ$508
includes taxes & fees
27 May - 28 May
Salvador's Studio by Brightwild | Heated Pool!
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (191)
"Everything about this place exceeded expectations. The check in was easy and they even let us store our luggage before our check in to make everything more conducive. The house is better than advertised, within walking distance to all the bars and restaurants."
The price is NZ$2,475
includes taxes & fees
27 May - 28 May
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (200)
"A very cozy little cottage in the heart of everything in Key West. In walking distance of everything, although bikes, golf carts and scooters are a great way to get around too. The front porch was nice to relax and sit on to finish out the day. Inside it was very clean, and had everything we needed for a short stay."
The price is NZ$951
includes taxes & fees
24 Jun - 25 Jun
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
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!
A heated pool
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, (55)
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is NZ$848
includes taxes & fees
10 Jun - 11 Jun
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
On the beach, sun-loungers, beach towels
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
9.2 out of 10, Wonderful, (109)
"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
Property grounds
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, (18)
"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!
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
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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.

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

Private beach, snorkelling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, (153)
"Stayed for a business trip and it was clean, comfortable, the staff is very friendly, a beautiful unit with a big balcony to relax and have a nice breakfast, lunch, or dinner, with comfy chairs and spacious table. The bathroom was updated as well as the whole unit. Very big and clean! We took our fur babies and there is a cute park for them to just roam around, or do some obstacle courses. Very clean and convenient. There is also a big heated pool with a jacuzzi, live music and a...
Sugarloaf Key Hotel at KOA Resort
6 outdoor pools, free pool cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1522)
"Loved this hotel, beautiful and well thought out comforts for travelers coming to Key West. Suite even had microwave we were not expecting. Daily room cleaning included refilling the Kcups and even giving me extra pillows on my bed. Hourly shuttle to Williams St. near Duval was great, and once we mastered the free Duval loop bus, location was great. Loved being able to text hotel staff with any requests and that they checked on your stay. Drive to hotel was through interesting area, but...
The price is NZ$419
includes taxes & fees
10 Jun - 11 Jun
Oceans Edge Key West Resort, Hotel & Marina
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1763)
"Amazing!!! "
The price is NZ$524
includes taxes & fees
4 Jun - 5 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sugarloaf Key holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sugarloaf Key. 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 Sugarloaf Key. Seeing all the best attractions is bound to make you fall in love with Sugarloaf Key. Who knows, you may even be tempted to extend your 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 holiday 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 Sugarloaf Key short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Sugarloaf Key?

Yes, there are holiday rentals close to the most popular sights in Sugarloaf Key, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Sugarloaf Key has a good selection of bars.

What are some of the best holiday rentals that Sugarloaf Key has to offer?

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

How many holiday rentals are there in Sugarloaf Key?

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

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 holiday rental in Sugarloaf Key like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sugarloaf Key. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.

Recent reviews of Sugarloaf Key properties
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