Holiday Rentals in Sugarloaf Key

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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 €229
includes taxes & fees
5 Oct - 6 Oct
Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (258)
"Really I have the best experience and soon I want to go again "
The price is €197
includes taxes & fees
5 Oct - 6 Oct
Old Wooden Bridge Resort and 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 €253
includes taxes & fees
4 Nov - 5 Nov
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (404)
"this was exactly as advertised and close to all the action"
The price is €239
includes taxes & fees
12 Oct - 13 Oct
Steps from Duval, Pool on Site & Bikes Included!

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

8.8 out of 10, Excellent, (231)
"Property was cute and in a great location! "
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

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

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is €288
includes taxes & fees
8 Oct - 9 Oct
Pelican Suite | Cozy Cottage, Hot Tubs, Close to 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

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 €247
includes taxes & fees
6 Oct - 7 Oct
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

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

9.6 out of 10, Exceptional, (81)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
Old Florida Style, wrap around porch, boat basin for dockage, open water

1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

The price is €297
includes taxes & fees
4 Nov - 5 Nov
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

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!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

10.0 out of 10, Exceptional, (190)
"Outstanding place to stay, centrally located!"
The price is €1,603
includes taxes & fees
14 Oct - 15 Oct
Perfect Location, Private Heated Pool, Pristine Luxury Home!

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 €441
includes taxes & fees
4 Nov - 5 Nov
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

9.6 out of 10, Exceptional, (18)
"Short walk to Duval street, quiet and very clean and comfortable."
The price is €281
includes taxes & fees
4 Nov - 5 Nov
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

Resort View 1BR Suite

2.0 star property
10.0 out of 10, Exceptional, (3)
"Cleanliness "
The price is €263
includes taxes & fees
5 Oct - 6 Oct
Resort View 1BR Suite

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

9.6 out of 10, Exceptional, (17)
"Great place to stay! Very clean and steps to Duval Ave."
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

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 €286
includes taxes & fees
27 Oct - 28 Oct
Island View 1BR Residence With Balcony

Living the Dream Key West Style

9.8 out of 10, Exceptional, (25)
"Great hosts and great accommodations!"
The price is €194
includes taxes & fees
5 Oct - 6 Oct
Living the Dream Key West Style

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

9.8 out of 10, Exceptional, (106)
"the condo was great roomingnice locationbeautiful, fun, great memories were made"
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
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, apart-hotels, 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 €194 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.