Sugarloaf Key Vacation Rentals

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Our top choices for Sugarloaf Key vacation rentals

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$896 nightly
The price is $1,008
Mar 12 - Mar 13
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
$1,398 nightly
The price is $1,547
Feb 17 - Feb 18
Total with taxes and fees
The Hemingway - Beach Houses Key West

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
$1,459 nightly
The price is $1,615
Feb 18 - Feb 19
Total with taxes and fees
The Lighthouse - Beach Houses Key West

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.
$1,032 nightly
The price is $1,144
Feb 20 - Feb 21
Total with taxes and fees
Private and Exclusive Florida Keys Getaway

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (10 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
$2,181 nightly
The price is $2,416
Mar 9 - Mar 10
Total with taxes and fees
Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
8.0 out of 10, Very Good, (2 reviews)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
$1,864 nightly
The price is $2,063
Feb 10 - Feb 11
Total with taxes and fees
Private and Exclusive Beach Getaway

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
$382 nightly
The price is $430
Mar 1 - Mar 2
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina
2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (160 reviews)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
$305 nightly
The price is $343
Feb 22 - Feb 23
Total with taxes and fees
Sunshine Key RV Resort & Marina

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (42 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
$480 nightly
The price is $533
Feb 25 - Feb 26
Total with taxes and fees
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, (299 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
$313 nightly
The price is $352
Feb 10 - Feb 11
Total with taxes and fees
Old Wooden Bridge Resort and Marina

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
$682 nightly
The price is $767
Feb 10 - Feb 11
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access

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
$1,075 nightly
The price is $1,209
Feb 10 - Feb 11
Total with taxes and fees
Atlantic View Luxury Villa with Pool

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
8.8 out of 10, Excellent, (55 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
$413 nightly
The price is $458
Feb 18 - Feb 19
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
$398 nightly
The price is $441
Feb 12 - Feb 13
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West

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

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (103 reviews)
"Great location. "
United States
Davian k.
$446 nightly
The price is $495
Feb 25 - Feb 26
Total with taxes and fees
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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)
"The cottage was clean and the location was nice and quiet. "
United States
Jaconica B.
$565 nightly
The price is $627
Feb 27 - Feb 28
Total with taxes and fees
Relax by Florida Keys Beaches, just a 7-min drive away

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

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$659 nightly
The price is $732
Mar 5 - Mar 6
Total with taxes and fees
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (143 reviews)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
$890 nightly
The price is $987
Mar 2 - Mar 3
Total with taxes and fees
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

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.
$431 nightly
The price is $479
Feb 22 - Feb 23
Total with taxes and fees
Waterfront Home

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
$338 nightly
The price is $369
Feb 11 - Feb 12
Total with taxes and fees
Star Room Barnacle Resort
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 $311 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.