Sugarloaf Key Holiday Rentals

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Holiday Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (259)
"I love this place!!!"
The price is AU$373
includes taxes & fees
17 Oct - 18 Oct
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (164)
"The stay was beautiful "
The price is AU$400
includes taxes & fees
16 Oct - 17 Oct
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very good, (314)
"Great hotel with excellent location "
The price is AU$467
includes taxes & fees
30 Oct - 31 Oct
Hyatt Vacation Club at Sunset Harbor, Key West
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (405)
"this was exactly as advertised and close to all the action"
The price is AU$348
includes taxes & fees
21 Oct - 22 Oct
Steps from Duval, Pool on Site & Bikes Included!
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
6.6 out of 10, (12)
"Unfortunately this stay was very disappointing. The marina was awesome. Tessa was awesome. The boat itself was disgusting. The pictures are very deceiving. What you see is not what you get. "
The price is AU$554
includes taxes & fees
22 Oct - 23 Oct
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
8.8 out of 10, Excellent, (232)
"Property was cute and in a great location! "
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
8.2 out of 10, Very good, (819)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
9.2 out of 10, Wonderful, (183)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
10.0 out of 10, Exceptional, (138)
"Great Location, Free Parking, comfortable beds"
Heart of Downtown Key West Cottage With Off-Street Parking
Comfortable Condo with Pool, Private Balcony, & Beach Access
8.6 out of 10, Excellent, (135)
"Nice area, location, and wonderful apartment!"
The price is AU$964
includes taxes & fees
11 Nov - 12 Nov
Comfortable Condo with Pool, Private Balcony, & Beach Access
Island View 1BR Residence With Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
The price is AU$503
includes taxes & fees
20 Oct - 21 Oct
Island View 1BR Residence With Balcony
Perfect Location, Private Heated Pool, Pristine Luxury Home!
10.0 out of 10, Exceptional, (191)
"Outstanding place to stay, centrally located!"
The price is AU$2,940
includes taxes & fees
21 Oct - 22 Oct
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.6 out of 10, Exceptional, (83)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
The price is AU$1,174
includes taxes & fees
8 Nov - 9 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, (190)
"Stayed for 2 weeks, very responsive to any questions/issues. Recommend staying here as it is close enough to the action, but far enough away to feel removed. "
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
9.8 out of 10, Exceptional, (47)
"Wonderful view, lot's of space, great location "
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
9.2 out of 10, Wonderful, (95)
"Great space for a large party! Having both houses with the driveway in the middle provided a great spot for our weekend!"
The price is AU$1,489
includes taxes & fees
13 Nov - 14 Nov
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
10.0 out of 10, Exceptional, (23)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is AU$631
includes taxes & fees
27 Oct - 28 Oct
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools
The price is AU$528
includes taxes & fees
16 Oct - 17 Oct
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools
Living the Dream Key West Style
9.8 out of 10, Exceptional, (27)
"Great hosts and great accommodations!"
The price is AU$527
includes taxes & fees
16 Oct - 17 Oct
Living the Dream Key West Style
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
9.8 out of 10, Exceptional, (24)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location and very nice room"
The price is AU$476
includes taxes & fees
16 Oct - 17 Oct
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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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Top Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Everything you need to know about Sugarloaf Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sugarloaf Key holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sugarloaf Key holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sugarloaf Key holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sugarloaf Key holiday rentals we have selected for you start as low as AU$348 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sugarloaf Key rentals

At Expedia, we put the best Sugarloaf Key holiday 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 holiday.

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.