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Our top choices for Sugarloaf Key vacation homes

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.
The price is ¥90,673
¥187,620 total
includes taxes & fees
May 10 - May 11
Private and Exclusive Florida Keys Getaway

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is ¥52,755
¥120,172 total
includes taxes & fees
May 8 - May 9
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.
The price is ¥144,214
¥267,784 total
includes taxes & fees
Jun 2 - Jun 3
The Hemingway - Beach Houses Key West

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is ¥81,139
¥148,599 total
includes taxes & fees
May 8 - May 9
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.
The price is ¥146,804
¥271,271 total
includes taxes & fees
May 20 - May 21
Private and Exclusive Beach Getaway

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is ¥29,675
¥92,894 total
includes taxes & fees
May 6 - May 7
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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.
Kelly's Kabin - Adorable Private Summerland Key Cottage

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

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (107 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is ¥21,824
¥64,962 total
includes taxes & fees
May 6 - May 7
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is ¥46,946
¥95,541 total
includes taxes & fees
Jun 2 - Jun 3
Paradise found

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

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is ¥39,095
¥88,004 total
includes taxes & fees
May 12 - May 13
SAVE BIG $$$ APRIL! OCEANFRONT 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, (98 reviews)
"We had a great time and will be back. "
United States
Michelle K.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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
The price is ¥54,954
¥106,846 total
includes taxes & fees
May 19 - May 20
Spanish Queen @Venture Out, Cudjoe Key

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very Good, (17 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is ¥30,664
¥70,453 total
includes taxes & fees
May 13 - May 14
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Keys 3 Bedroom Corner Home near Beach & Key West

Keys 3 Bedroom Corner Home near Beach & Key West
Sands
9.4 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay"
United States
Patricia H.
The price is ¥51,656
¥119,641 total
includes taxes & fees
May 6 - May 7
Keys 3 Bedroom Corner Home near Beach & 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, (166 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 ¥49,458
¥102,587 total
includes taxes & fees
May 8 - May 9
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

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, (155 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.
The price is ¥52,991
¥107,032 total
includes taxes & fees
May 8 - May 9
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is ¥39,567
¥105,277 total
includes taxes & fees
May 6 - May 7
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is ¥31,323
¥94,276 total
includes taxes & fees
May 7 - May 8
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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 ¥37,996
¥102,940 total
includes taxes & fees
May 31 - Jun 1
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

Find out more about Sugarloaf Key

Sugarloaf Key Vacation Homes information

Number of reviews
903
Accommodation
854 Vacation Homes
Lowest Price
¥64,962
Highest Price
¥271,271

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