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 | Flat-screen TV
Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (126)
"Amazing stay in a boat!"
The price is ￥21,812
￥40,231 total
includes taxes & fees
Jun 3 - Jun 4
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, (331)
"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 ￥15,535
￥37,289 total
includes taxes & fees
May 30 - May 31
Steps from Duval, Pool & Bikes $129-$299 Night!
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
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Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (17)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is ￥33,895
￥57,493 total
includes taxes & fees
Jun 4 - Jun 5
Poolside Cottage #411
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
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!
Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (88)
"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 ￥18,301
￥42,699 total
includes taxes & fees
Jun 3 - Jun 4
Aqua Lodges at Hurricane Hole Marina
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pool | Outdoor pool, a heated 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
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
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, (229)
"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 ￥47,012
￥90,939 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!
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 ￥18,203
￥42,507 total
includes taxes & fees
Jun 5 - Jun 6
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
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, (94)
"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 ￥18,396
￥42,297 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!
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 ￥19,025
￥43,161 total
includes taxes & fees
May 30 - May 31
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
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 ￥20,243
￥46,744 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!
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (192)
"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 ￥109,687
￥238,499 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
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (201)
"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 ￥30,188
￥75,079 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!
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!
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 ￥34,276
￥72,936 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
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
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
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!
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
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.

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, (160)
"Great!"
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, (1509)
"Excellent resort "
The price is ￥27,724
￥40,345 total
includes taxes & fees
Jun 10 - Jun 11
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, (1768)
"Great hotel, I would come back anytime. "
The price is ￥36,006
￥50,463 total
includes taxes & fees
Jun 4 - Jun 5
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.

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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

Southernmost Beach Resort

Southernmost Beach Resort

5/5 Excellent
Nice
"Just have to bring your own blow dryer."
A verified traveler stayed at Southernmost Beach Resort
Posted 4 hours ago
Southernmost Beach Resort