Sugarloaf Key Vacation Rentals

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Vacation Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (266)
"I love this place!!!"
United States
Greg
$259 nightly
The price is $292
Nov 4 - Nov 5
Total with taxes and fees
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
$283 nightly
The price is $319
Nov 11 - Nov 12
Total with taxes and fees
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)
"Good location "
United States
Paula
$278 nightly
The price is $312
Nov 12 - Nov 13
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (407)
"Great place to stay and walk to all the attractions."
United States
Byron Debi L.
$204 nightly
The price is $227
Nov 16 - Nov 17
Total with taxes and fees
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, (820)
"Overall a good place to stay and value for money "
United States
Vijay Bhasker
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)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
United States
p j.
$336 nightly
The price is $372
Nov 11 - Nov 12
Total with taxes and fees
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, (140)
"Wonderful property. Perfect location. Clean building. Everything you needed for a relaxing stay. Lovely hosts as well. Will stay there again. "
United States
Andrew C.
Heart of Downtown Key West Cottage With Off-Street Parking
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
$335 nightly
The price is $377
Nov 4 - Nov 5
Total with taxes and fees
Island View 1BR Residence With Balcony
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
8.6 out of 10, Excellent, (139)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
$335 nightly
The price is $371
Nov 10 - Nov 11
Total with taxes and fees
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Perfect Location, Private Heated Pool, Pristine Luxury Home!
10.0 out of 10, Exceptional, (192)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
$1,595 nightly
The price is $1,770
Nov 10 - Nov 11
Total with taxes and fees
Perfect Location, Private Heated Pool, Pristine Luxury Home!
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!
Wahoo Way | Charming Hideaway On Duval Street!
9.0 out of 10, Wonderful, (17)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Easy walks to everything!"
United States
Don N.
$297 nightly
The price is $326
Nov 17 - Nov 18
Total with taxes and fees
Wahoo Way | Charming Hideaway On Duval Street!
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
9.2 out of 10, Wonderful, (184)
"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 in the middle of everything"
United States
Loyd K.
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
10.0 out of 10, Exceptional, (23)
"Great location and getaway. Steps away from Duval street and restaurants. Highly recommend!"
United States
Alex J.
$348 nightly
The price is $383
Nov 30 - Dec 1
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Super-Cozy boat in Key West!
$283 nightly
The price is $314
Nov 4 - Nov 5
Total with taxes and fees
Super-Cozy boat in Key West!
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (238)
"Clean, convenient, and excellent host!"
United States
Tony K.
$851 nightly
The price is $944
Nov 4 - Nov 5
Total with taxes and fees
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
Living the Dream Key West Style
10.0 out of 10, Exceptional, (31)
"Clean rooms pet friendly great view! Exactly as advertised "
United States
Todd
$307 nightly
The price is $341
Nov 11 - Nov 12
Total with taxes and fees
Living the Dream Key West Style
Kingfish Keep | Lively Escape on Duval! Balcony!
9.8 out of 10, Exceptional, (19)
"Awesome location with excellent communication. "
United States
Gary W.
$371 nightly
The price is $408
Nov 16 - Nov 17
Total with taxes and fees
Kingfish Keep | Lively Escape on Duval! Balcony!
FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!
9.8 out of 10, Exceptional, (141)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful location, clean, cozy and very private. I will definitely return.."
United States
Teresa K.
$211 nightly
The price is $234
Nov 4 - Nov 5
Total with taxes and fees
FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!
The Grenada Suite Pool View Private Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
$543 nightly
The price is $611
Nov 19 - Nov 20
Total with taxes and fees
The Grenada Suite Pool View Private Balcony
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 vacation rentals

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

Sugarloaf Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sugarloaf Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $227 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sugarloaf Key rentals

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

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.