Lower Sugarloaf Key Holiday Rentals

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Holiday Rentals in Lower Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (267)
"I love this place!!!"
United States
Greg
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (165)
"The stay was beautiful "
United States
Jennifer
The price is NZ$537
includes taxes & fees
10 Nov - 11 Nov
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very good, (314)
"Good location "
United States
Paula
The price is NZ$507
includes taxes & fees
8 Dec - 9 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
8.2 out of 10, Very good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
The price is NZ$596
includes taxes & fees
9 Nov - 10 Nov
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (157)
"Great location and very happy with our accommodations."
United States
Carrie B.
The price is NZ$563
includes taxes & fees
15 Nov - 16 Nov
Cottage with Pool and Dockage, just minutes to Key West

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
United States
Edward H.
The price is NZ$771
includes taxes & fees
24 Nov - 25 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
9.0 out of 10, Wonderful, (88)
"Community is great, location in the Keys is great, house was perfect for our family of 3."
United States
Christina H.
The price is NZ$697
includes taxes & fees
16 Nov - 17 Nov
Canal front, dockage, 2 bedroom, 2 bath

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Old Town Key West
9.6 out of 10, Exceptional, (29)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
United States
Dianna F.
The price is NZ$621
includes taxes & fees
24 Nov - 25 Nov
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (119)
"Great location for some much needed time away."
United States
Brad R.
The price is NZ$1,020
includes taxes & fees
30 Nov - 1 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage

NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"Great property, owners were very helpful and we really enjoyed our stay!"
United States
Lee J.
The price is NZ$931
includes taxes & fees
9 Nov - 10 Nov
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Sands
The price is NZ$1,005
includes taxes & fees
11 Nov - 12 Nov
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

Meadows
10.0 out of 10, Exceptional, (23)
"My husband and I stayed at this property for our anniversary week. "
United States
Claudia S.
The price is NZ$709
includes taxes & fees
1 Dec - 2 Dec
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

Old Town Key West
9.6 out of 10, Exceptional, (141)
"Wonderful and quiet property but in walking distance to the excitement. Great communication and easy check in and check out. We will be back!"
United States
Krista
The price is NZ$419
includes taxes & fees
12 Nov - 13 Nov
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

Living the Dream Key West Style

Stock Island
10.0 out of 10, Exceptional, (31)
"Clean rooms pet friendly great view! Exactly as advertised "
United States
Todd
The price is NZ$603
includes taxes & fees
11 Nov - 12 Nov
Living the Dream Key West Style

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Cudjoe Key
9.8 out of 10, Exceptional, (26)
"Renting was easy and hassle free."
United States
chuck s.
The price is NZ$1,089
includes taxes & fees
9 Nov - 10 Nov
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

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

Little Torch Key
9.6 out of 10, Exceptional, (84)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
The price is NZ$1,227
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water

Comfortable Condo with Pool, Private Balcony, & Beach Access

Beachside
8.6 out of 10, Excellent, (137)
"Place was perfect for a family of 6. Very nice layout. Pool and spa were very nice. You could look out and see the ocean in the distance but no real beach access. It was visible but you can’t get to it from the property. Although it is right up the street on either side of the property so that was nice. The only downfall to this place is we got eaten up by what seems to have been fleas."
United States
Dorothy R.
The price is NZ$1,020
includes taxes & fees
11 Nov - 12 Nov
Comfortable Condo with Pool, Private Balcony, & Beach Access

JULIE ~ Adult Only, 1st Floor King Bedroom w/ Shared Pool, Scarlet Mango Inn!

Old Town Key West
10.0 out of 10, Exceptional, (75)
"Excellent."
United States
Matt M.
The price is NZ$551
includes taxes & fees
10 Nov - 11 Nov
JULIE ~ Adult Only, 1st Floor King Bedroom w/ Shared Pool, Scarlet Mango Inn!

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

Stock Island
7.8 out of 10, Good, (23)
"The resort was amazing- we really enjoyed the house boat and Marina life- thank you for sharing and your great communication"
United States
Maureen M.
The price is NZ$896
includes taxes & fees
3 Dec - 4 Dec
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Palm - Beach Houses Key West

Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
United States
Crystal G.
The price is NZ$2,721
includes taxes & fees
19 Nov - 20 Nov
Palm - Beach Houses Key West
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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Find out more about Lower Sugarloaf Key

Everything you need to know about Lower 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 Lower 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 Lower Sugarloaf Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lower Sugarloaf Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lower 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 Lower 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 Lower Sugarloaf Key holiday rentals we have selected for you start as low as NZ$402 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lower Sugarloaf Key rentals

At Expedia, we put the best Lower 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 Lower 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 Lower 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 Lower 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.