Lower Sugarloaf Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (299 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
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, (175 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is NZ$684
includes taxes & fees
1 Mar - 2 Mar
Aqua Lodges at Hurricane Hole Marina

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (103 reviews)
"Great location. "
United States
Davian k.
The price is NZ$823
includes taxes & fees
25 Feb - 26 Feb
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is NZ$753
includes taxes & fees
9 Feb - 10 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (165 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is NZ$527
includes taxes & fees
15 Feb - 16 Feb
Cottage with swimming pool and dockage, just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is NZ$1,875
includes taxes & fees
9 Feb - 10 Feb
Atlantic View Luxury Villa with Pool

Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location - quiet and secluded - away from everything but not so far away that you felt isolated. All very clean and amenities were as described."
United Kingdom
Robert
The price is NZ$624
includes taxes & fees
11 Feb - 12 Feb
Star Room Barnacle Resort

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (177 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is NZ$805
includes taxes & fees
22 Feb - 23 Feb
Waterfront Home

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
Kelly's Kabin - Adorable Private Summerland Key Cottage

Relax by Florida Keys Beaches, just a 7-min drive away

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (201 reviews)
"Will definitely stay here again "
United States
Jeannine R.
The price is NZ$1,083
includes taxes & fees
27 Feb - 28 Feb
Relax by Florida Keys Beaches, just a 7-min drive away

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is NZ$2,532
includes taxes & fees
25 Feb - 26 Feb
Grand Marina Suite by Brightwild Waterfront

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, (29 reviews)
"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 NZ$823
includes taxes & fees
9 Mar - 10 Mar
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is NZ$1,889
includes taxes & fees
20 Feb - 21 Feb
Private and Exclusive Florida Keys Getaway

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is NZ$1,126
includes taxes & fees
16 Feb - 17 Feb
Spanish Queen @Venture Out, Cudjoe Key

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is NZ$1,200
includes taxes & fees
5 Mar - 6 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is NZ$2,749
includes taxes & fees
12 Feb - 13 Feb
The Seagate Estate at Lunara Bay

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful "
United States
Lisa P.
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (143 reviews)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is NZ$820
includes taxes & fees
4 Mar - 5 Mar
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (41 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is NZ$1,069
includes taxes & fees
9 Mar - 10 Mar
Living the Dream Key West Style
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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$522 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.