Sugarloaf Key Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (261)
"I love this place!!!"
United States
Greg
The price is NZ$424
includes taxes & fees
28 Oct - 29 Oct
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (165)
"The stay was beautiful "
United States
Jennifer
The price is NZ$478
includes taxes & fees
27 Oct - 28 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 "
United States
Rony
The price is NZ$494
includes taxes & fees
29 Oct - 30 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"
Canada
Dave T.
The price is NZ$391
includes taxes & fees
27 Oct - 28 Oct
Steps from Duval, Pool on Site & Bikes Included!
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"
United States
Eric
Coconut Mallory Resort And Marina By Kees Vacations
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. "
United States
Christine
The price is NZ$601
includes taxes & fees
27 Oct - 28 Oct
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Heart of Downtown Key West Cottage With Off-Street Parking
10.0 out of 10, Exceptional, (138)
"Great Location, Free Parking, comfortable beds"
United States
Vanessa C.
Heart of Downtown Key West Cottage With Off-Street Parking
Perfect Location, Private Heated Pool, Pristine Luxury Home!
10.0 out of 10, Exceptional, (191)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
The price is NZ$3,300
includes taxes & fees
28 Oct - 29 Oct
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Comfortable Condo with Pool, Private Balcony, & Beach Access
8.6 out of 10, Excellent, (135)
"Nice area, location, and wonderful apartment!"
United States
Harald P.
The price is NZ$995
includes taxes & fees
26 Oct - 27 Oct
Comfortable Condo with Pool, Private Balcony, & Beach Access
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
9.2 out of 10, Wonderful, (183)
"Great location; excellent property management "
United States
Frank T.
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
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."
United States
Julia P.
The price is NZ$620
includes taxes & fees
23 Oct - 24 Oct
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
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."
United States
Tonya
The price is NZ$656
includes taxes & fees
26 Oct - 27 Oct
Island View 1BR Residence With Balcony
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. "
United States
Spencer A.
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, (48)
"Wonderful view, lot's of space, great location "
United States
Valerie
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
Living the Dream Key West Style
9.8 out of 10, Exceptional, (28)
"Great hosts and great accommodations!"
United States
Nancy M.
The price is NZ$661
includes taxes & fees
11 Nov - 12 Nov
Living the Dream Key West Style
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
8.6 out of 10, Excellent, (138)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is NZ$653
includes taxes & fees
2 Nov - 3 Nov
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Kingfish Keep | Lively Escape on Duval! Balcony!
10.0 out of 10, Exceptional, (18)
"Awesome location with excellent communication. "
United States
Gary W.
The price is NZ$712
includes taxes & fees
26 Oct - 27 Oct
Kingfish Keep | Lively Escape on Duval! Balcony!
Resort View 1BR Suite
2.0 star property
9.0 out of 10, Wonderful, (4)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is NZ$629
includes taxes & fees
26 Oct - 27 Oct
Resort View 1BR Suite
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! "
United States
Brandie P.
The price is NZ$423
includes taxes & fees
16 Nov - 17 Nov
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
7.8 out of 10, Good, (22)
"Loved everything about the stay, "
United States
Kurt W.
The price is NZ$880
includes taxes & fees
28 Oct - 29 Oct
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$391 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 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.