A waterfront with a pier, calm water, and houses with palm trees in the background.

Sugarloaf Key Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Sugarloaf Key vacation rentals

Terrace/patio

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.
$626 nightly
The price is $695
Aug 12 - Aug 13
Total with taxes and fees
Starlight Serenity - Hideaway with Stunning Views
House | 2 bedrooms, Internet

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
$734 nightly
The price is $825
Aug 12 - Aug 13
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
Pool

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
$1,222 nightly
The price is $1,352
Jul 18 - Jul 19
Total with taxes and fees
Private and Exclusive Florida Keys Getaway
Pool

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (11 reviews)
"Location was amazing. Lots of great local restaurants and food markets nearby. Property was gorgeous, very private, and spacious interiors. Beds were so comfortable! Friendly staff and the pool was a 10 out of 10!! I will be back. "
United States
Joanna G.
$1,861 nightly
The price is $2,059
Jul 21 - Jul 22
Total with taxes and fees
Private and Exclusive Beach Getaway
Pool

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.
$1,537 nightly
The price is $1,702
Jul 25 - Jul 26
Total with taxes and fees
The Hemingway - Beach Houses Key West
Pool

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.
$2,120 nightly
The price is $2,347
Aug 3 - Aug 4
Total with taxes and fees
Private and Exclusive Beach Getaway
1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (353 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
$254 nightly
The price is $286
Jul 15 - Jul 16
Total with taxes and fees
Old Wooden Bridge Resort and Marina
Outdoor dining

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.4 out of 10, Exceptional, (173 reviews)
"Great place "
United States
David
$346 nightly
The price is $383
Jul 15 - Jul 16
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
Outdoor pool, a heated 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
8.6 out of 10, Excellent, (98 reviews)
"Perfect location. Privacy and comfort."
United States
Anthony
$362 nightly
The price is $401
Aug 1 - Aug 2
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor pool

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, (39 reviews)
"Perfect location! Had options of 2 pools to enjoy on property. The marina serves complimentary coffee. "
United States
Crystal A.
$372 nightly
The price is $413
Aug 3 - Aug 4
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Exterior

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (93 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
$388 nightly
The price is $431
Jul 15 - Jul 16
Total with taxes and fees
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Property grounds

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)
"All was excellent "
United States
Bryan M.
$532 nightly
The price is $591
Jul 24 - Jul 25
Total with taxes and fees
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Property grounds

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, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
$537 nightly
The price is $596
Jul 15 - Jul 16
Total with taxes and fees
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Fridge, microwave, oven, stovetop

Canal-view 2BR/2BA home with pool, hot tub, and dock access.

Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Cudjoe Key
9.2 out of 10, Wonderful, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
$555 nightly
The price is $616
Jul 26 - Jul 27
Total with taxes and fees
Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (192 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
$275 nightly
The price is $309
Jul 16 - Jul 17
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Exterior detail

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
$595 nightly
The price is $660
Jul 26 - Jul 27
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (125 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
$452 nightly
The price is $501
Aug 12 - Aug 13
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
Exterior

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
8.8 out of 10, Excellent, (101 reviews)
"short drive to downtown of course as long as traffic allows it...quiet stay beautiful views...bring mosquito repellent. "
United States
Lismary D.
$646 nightly
The price is $717
Jul 22 - Jul 23
Total with taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Outdoor dining

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
$554 nightly
The price is $615
Aug 2 - Aug 3
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 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
Jul 15 - Jul 16
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key
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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"The room was super clean that was great! AC was super cold and that was huge, definitely need cold AC. There are a lot of amenities, which is great. Though the restaurant/bar closes too early, 10pm seems way too early for a hotel/resort in Key West. Also, would have been nice breakfast was more easily accessible. We were on the 3rd floor, and the elevator was not working properly, the button to call it to go down was not working so we called it to go up, and then once inside the elevator, the button for the 1st floor wasn’t working, so we then had to go walk down from the 4th floor with our luggage to get to our truck. When we checked out the staff wrote down our concerns with the elevator, though didn’t even offer to discount our stay for the huge inconvenience. Overall the stay was good but it could have been better."
Evans 1-night trip
Posted 2 hours ago
Blue Flamingo Resort Key West

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 $238 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.

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