Sugarloaf Key Vacation Rentals

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Our top choices for Sugarloaf Key vacation rentals

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.
$1,084 nightly
The price is $1,200
May 26 - May 27
Total with taxes and fees
Private and Exclusive Florida Keys Getaway

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
$614 nightly
The price is $682
May 24 - May 25
Total with taxes and fees
Starlight Serenity - Hideaway with 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)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
United States
Brian K.
$1,541 nightly
The price is $1,706
Jun 2 - Jun 3
Total with taxes and fees
The Hemingway - Beach Houses Key West

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$738 nightly
The price is $830
May 24 - May 25
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (11 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
$1,561 nightly
The price is $1,728
May 20 - May 21
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.
$2,457 nightly
The price is $2,721
Jun 9 - Jun 10
Total with taxes and fees
Private and Exclusive Beach Getaway

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (37 reviews)
"The location was fabulous, due to the hotel’s amenities. Ie the hourly transport to downtown.pools and restaurants. The accommodations were a bit dated but adequate. The host responded immediately to our request! "
United States
Leigh P.
$451 nightly
The price is $501
May 20 - May 21
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (186 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
$298 nightly
The price is $335
May 27 - May 28
Total with taxes and fees
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, (60 reviews)
"Friendly host and unique location"
United States
Scott
$361 nightly
The price is $401
May 20 - May 21
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, (338 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
$254 nightly
The price is $286
May 21 - May 22
Total with taxes and fees
Old Wooden Bridge Resort and Marina

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
9.0 out of 10, Wonderful, (62 reviews)
"The location was very good and the host was responsive. "
United States
Lilly A.
$359 nightly
The price is $398
May 20 - May 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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, (171 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
$265 nightly
The price is $294
May 27 - May 28
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
"Host was great!!! Unit very clean well stocked with beautiful view."
United States
Lisa F.
$375 nightly
The price is $416
Jun 2 - Jun 3
Total with taxes and fees
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (89 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
$433 nightly
The price is $481
May 20 - May 21
Total with taxes and fees
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (99 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
$381 nightly
The price is $423
May 22 - May 23
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

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, (105 reviews)
"Wonderful family getaway"
United States
Anthony V.
$697 nightly
The price is $773
Jun 2 - Jun 3
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (25 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
$609 nightly
The price is $677
May 20 - May 21
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

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)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
$447 nightly
The price is $496
Jun 18 - Jun 19
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (157 reviews)
"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "
United States
Peggy H.
$563 nightly
The price is $624
Jun 2 - Jun 3
Total with taxes and fees
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (168 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
$629 nightly
The price is $698
Jun 3 - Jun 4
Total with taxes and fees
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from 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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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 $262 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.