Holiday Rentals in Lower Sugarloaf Key

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Our top choices for Lower Sugarloaf Key holiday rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (278)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is €254
includes taxes & fees
14 Dec - 15 Dec
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.4 out of 10, Very good, (320)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is €278
includes taxes & fees
15 Dec - 16 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (412)
"Everything was excellent!"
United States
Susan L.
The price is €199
includes taxes & fees
15 Dec - 16 Dec
Steps from Duval, Pool on Site & Bikes Included!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (27)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
The price is €335
includes taxes & fees
15 Dec - 16 Dec
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking
Key West Historic District
10.0 out of 10, Exceptional, (142)
"Perfect location! Cute cottage had the best time. "
United States
jamie r.
Heart of Downtown Key West Cottage With Off-Street Parking

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

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is €437
includes taxes & fees
14 Dec - 15 Dec
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!

Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!
2.0 star property
Stock Island
Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
2.0 star property
Old Town Key West
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (31)
"Great place, great location, great communication from host!"
United States
Lara P.
The price is €497
includes taxes & fees
14 Dec - 15 Dec
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

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

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (25)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is €335
includes taxes & fees
17 Dec - 18 Dec
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

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

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

Private Heated Pool & Near Duval - The Curry House

Private Heated Pool & Near Duval - The Curry House
Old Town Key West
10.0 out of 10, Exceptional, (6)
"Great property! "
United States
Austin C.
The price is €3,725
includes taxes & fees
12 Jan - 13 Jan 2026
Private Heated Pool & Near Duval - The Curry House

Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
Key West
8.2 out of 10, Very good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
9.8 out of 10, Exceptional, (36)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
The price is €299
includes taxes & fees
15 Dec - 16 Dec
Living the Dream Key West Style

Heated Pool, Steps to Duval St - Poolside Paradise

Heated Pool, Steps to Duval St - Poolside Paradise
Old Town Key West
9.2 out of 10, Wonderful, (18)
"Great location"
United States
Peter S.
Heated Pool, Steps to Duval St - Poolside Paradise

King Suite with Balcony - The James House

King Suite with Balcony - The James House
Key West Historic District
9.8 out of 10, Exceptional, (8)
"This property and room where great . It had everything you needed and was clean The location was absolutely great. Near to all restaurants and shopping. You can park your car and walk to it all or rent a scooter next door and get around town with no worries of parking. We will be back again and would recommend to anyone that wants to visit key west . Thank you for a great place"
United States
david q.
The price is €413
includes taxes & fees
23 Dec - 24 Dec
King Suite with Balcony - The James House

Spacious home with pool & balcony - 1 block from Duval Street

Spacious home with pool & balcony - 1 block from Duval Street
Key West Historic District
9.2 out of 10, Wonderful, (84)
"Great location! Close to all the activities."
United States
susan h.
Spacious home with pool & balcony - 1 block from Duval Street

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!
Old Town Key West
10.0 out of 10, Exceptional, (195)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Harbor Walk Hideaways | Group Compound In Old Town!

Harbor Walk Hideaways | Group Compound In Old Town!
Key West Historic District
9.8 out of 10, Exceptional, (10)
"We had an amazing time and you can’t beat this location! Rooms were clean and cozy, our group enjoyed and spent a lot of time in the courtyard as well. Extremely accommodating and great communication throughout our stay, always felt like our comfort was their priority. "
United States
Brian W.
Harbor Walk Hideaways | Group Compound In Old Town!
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 Lower Sugarloaf Key Hotel Reviews

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, 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 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 €199 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.