Sugarloaf Key Holiday Rentals

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Holiday Rentals in Sugarloaf Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (162)
"The stay was beautiful "
The price is NZ$468
includes taxes & fees
9 Sept - 10 Sept
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, (312)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is NZ$541
includes taxes & fees
8 Sept - 9 Sept
Hyatt Vacation Club at Sunset Harbor, Key West

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (257)
"River boat houses, pool, kayak rentals. "
The price is NZ$393
includes taxes & fees
8 Sept - 9 Sept
Old Wooden Bridge Resort and Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (400)
"Great location. The bike was an awesome way to get around. Pool was very clean and refreshing. "
The price is NZ$384
includes taxes & fees
21 Sept - 22 Sept
Steps from Duval, Pool on Site & Bikes Included!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (141)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is NZ$416
includes taxes & fees
20 Sept - 21 Sept
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (181)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (188)
"The location was perfect for exploring and getting places in key West. It had a relaxing vibe that was perfect for vacation. "
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is NZ$527
includes taxes & fees
21 Sept - 22 Sept
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (79)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (16)
"Great place to stay! Very clean and steps to Duval Ave."
The price is NZ$640
includes taxes & fees
21 Sept - 22 Sept
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

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

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (144)
"We had a great stay places is amazing"
The price is NZ$409
includes taxes & fees
21 Sept - 22 Sept
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (134)
"This was the cutest cottage and AC was cranking. It was so hot when we went that the house was so refreshing to walk into. The place was clean and had everything we needed. It was the perfect spot to walk to all the restaurants and shops. Loved it!!"
Heart of Downtown Key West Cottage With Off-Street Parking

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (3)
"Beautiful property, perfectly located, and one of the best VRBO experiences we have ever had."
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (55)
"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 place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

7.8 out of 10, Good, (22)
"Loved everything about the stay, "
The price is NZ$847
includes taxes & fees
14 Sept - 15 Sept
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (135)
"Beautiful home with everything needed for a fun family vacation"
Oversized home for the whole family w/private pool & dock

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

9.8 out of 10, Exceptional, (129)
"Beautiful property & great location with stunning views. "
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

Living the Dream Key West Style

9.8 out of 10, Exceptional, (22)
"Great hosts and great accommodations!"
The price is NZ$570
includes taxes & fees
13 Sept - 14 Sept
Living the Dream Key West Style

Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool

9.0 out of 10, Wonderful, (57)
"Property suited us perfectly. "
Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
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

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$384 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.