Sugarloaf Key Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Sugarloaf Key vacation rentals

House | 2 bedrooms, Internet

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is ￥80,714
￥145,005 total
includes taxes & fees
Jun 17 - Jun 18
Starlight Serenity - Hideaway w Stunning Views
Pool

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.
The price is ￥189,664
￥315,661 total
includes taxes & fees
Jun 24 - Jun 25
Private and Exclusive Beach Getaway
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.
The price is ￥193,177
￥353,517 total
includes taxes & fees
Jun 3 - Jun 4
Private and Exclusive Beach Getaway
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.
The price is ￥56,356
￥127,003 total
includes taxes & fees
Jun 17 - Jun 18
Starlight Serenity - Hideaway with Stunning Views
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
The price is ￥50,966
￥64,345 total
includes taxes & fees
Jun 3 - Jun 4
Living the Dream Key West Style
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (187 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is ￥18,491
￥47,500 total
includes taxes & fees
Jun 8 - Jun 9
Aqua Lodges at Hurricane Hole Marina
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, (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.
The price is ￥31,376
￥69,821 total
includes taxes & fees
Jun 3 - Jun 4
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
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, (342 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is ￥19,030
￥43,858 total
includes taxes & fees
Jun 9 - Jun 10
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
9.2 out of 10, Wonderful, (170 reviews)
"Great place "
United States
David
The price is ￥28,669
￥56,541 total
includes taxes & fees
Jun 3 - Jun 4
Cottage with Pool and Dockage, just minutes to Key West
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, (158 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.
The price is ￥46,586
￥99,395 total
includes taxes & fees
Jun 3 - Jun 4
Cudjoe Cottages, swimming pool, just 20 miles from Key West
House | Exterior

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is ￥47,164
￥66,890 total
includes taxes & fees
Jun 8 - Jun 9
Resort View 1BR Suite With Direct Pool Access
Outdoor dining

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
The price is ￥28,669
￥63,291 total
includes taxes & fees
Jun 4 - Jun 5
Canal front, dockage, 2 bedroom, 2 bath
Exterior

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, (170 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
The price is ￥50,170
￥104,064 total
includes taxes & fees
Jun 3 - Jun 4
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Outdoor pool, a heated pool

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (71 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is ￥159,111
￥307,452 total
includes taxes & fees
Jun 26 - Jun 27
One of the very few beach houses with a daily, rental license in the Keys.
Terrace/patio

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (186 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is ￥31,854
￥65,919 total
includes taxes & fees
Jun 23 - Jun 24
Waterfront Home
A heated pool

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 ￥58,671
￥140,603 total
includes taxes & fees
Jun 3 - Jun 4
Post Card Point #319 - Ocean Views!
Exterior

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise
Cudjoe Key
9.6 out of 10, Exceptional, (53 reviews)
"Great place!"
United States
Piotr P.
The price is ￥67,053
￥138,019 total
includes taxes & fees
Jun 3 - Jun 4
Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise
A heated pool

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, (146 reviews)
"Beautiful location and house. The house is well stocked and very clean. Definitely a 5 star experience!"
United States
Lisa D.
The price is ￥91,978
￥173,078 total
includes taxes & fees
Jun 7 - Jun 8
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Exterior

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

SAVE BIG $$$ JUNE!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (90 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is ￥28,509
￥75,454 total
includes taxes & fees
Jun 8 - Jun 9
SAVE BIG $$$ JUNE!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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, (4 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is ￥36,266
￥101,541 total
includes taxes & fees
Jun 3 - Jun 4
Charming 2-bedroom house with WiFi, AC in lovely 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

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

8/10 Good
"Room was clean. The Yellow Fin does not have much of a selection on the menu. Did not like that The coffee shop closes at 11:00 am. After that you have to make your own coffee in your room. The pool waitress Collette Crooks was excellent very friendly and attentive. Our room was on the second floor which had no ice machine. Not happy with having to get on the elevator to go to the first floor for ice especially at night."
Ronald 5-night trip
Posted 3 hours ago
Oceans Edge Key West Resort, Hotel & Marina

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