Sugarloaf Key Holiday Rentals

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Our top choices for Sugarloaf Key holiday rentals

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is AU$918
includes taxes & fees
14 Apr - 15 Apr
Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is AU$989
includes taxes & fees
14 Apr - 15 Apr
Starlight Serenity - Hideaway w Stunning Views

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

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.6 out of 10, Good, (34 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 AU$709
includes taxes & fees
22 Apr - 23 Apr
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (182 reviews)
"Great stay better than we expected "
Canada
Jordan
The price is AU$458
includes taxes & fees
3 May - 4 May
Aqua Lodges at Hurricane Hole Marina

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (57 reviews)
"everything was perfect"
United States
Kathy A
The price is AU$569
includes taxes & fees
16 Apr - 17 Apr
Living the Dream Key West Style

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (320 reviews)
"Staff was great. Walking distance to No Name Pub. Water view was terrific. The bridge to nowhere was a good walk."
United States
Amado
The price is AU$409
includes taxes & fees
10 May - 11 May
Old Wooden Bridge Resort and Marina

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (162 reviews)
"Stayed one night, conveniently located. "
United States
Wendy H.
The price is AU$398
includes taxes & fees
14 Apr - 15 Apr
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (167 reviews)
"Great place "
United States
David
Cottage with Pool and Dockage, just minutes to Key West

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (199 reviews)
"Excellent location for staying in the Lower Keys. Sunrise view. Nice neighborhood setting. Close to real good places to eat, listen to music and chill. Would come back. "
United States
Ihor C.
Direct Oceanfront Cottage-Sunrise View- #2,

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

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is AU$699
includes taxes & fees
19 Apr - 20 Apr
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"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 AU$1,453
includes taxes & fees
17 Apr - 18 Apr
Atlantic View Luxury Villa with Pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (24 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 AU$967
includes taxes & fees
20 Apr - 21 Apr
Spanish Queen @Venture Out, Cudjoe Key

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

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (104 reviews)
"Wonderful family getaway"
United States
Anthony V.
The price is AU$1,118
includes taxes & fees
27 Apr - 28 Apr
Old Florida Style, wrap around porch, boat basin for dockage, open water

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is AU$722
includes taxes & fees
3 May - 4 May
Kelly's Kabin - Adorable Private Summerland Key Cottage

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

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (106 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is AU$701
includes taxes & fees
14 Apr - 15 Apr
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (96 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is AU$1,077
includes taxes & fees
21 Apr - 22 Apr
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (13 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is AU$1,038
includes taxes & fees
27 Apr - 28 Apr
House of the Rising Sun - VO479

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, (6 reviews)
"Beautiful "
United States
Lisa P.
The price is AU$1,281
includes taxes & fees
21 Apr - 22 Apr
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (29 reviews)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
The price is AU$920
includes taxes & fees
19 Apr - 20 Apr
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (54 reviews)
"Great location in the complex and in the Keys themselves."
United States
Karl S.
The price is AU$1,279
includes taxes & fees
11 May - 12 May
Post Card Point #319 - Ocean Views!
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 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, 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 favourite 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 depend 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 AU$372 per night. Entering your travel dates in the search wizard might find you 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.