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

Sugarloaf Key Vacation Rentals

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Our top choices for Sugarloaf Key vacation homes

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
The price is CA $428
CA $983 total
includes taxes & fees
Jul 8 - Jul 9
Starlight Serenity - Hideaway w Stunning Views

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.
The price is CA $1,242
CA $2,305 total
includes taxes & fees
Jul 13 - Jul 14
The Lighthouse - Beach Houses Key West

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.
The price is CA $1,687
CA $2,924 total
includes taxes & fees
Jul 26 - Jul 27
Private and Exclusive Beach Getaway

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 CA $1,304
CA $2,422 total
includes taxes & fees
Jul 14 - Jul 15
The Hemingway - Beach Houses Key West

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 CA $285
CA $854 total
includes taxes & fees
Jul 8 - Jul 9
Starlight Serenity - Hideaway with Stunning Views

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
The price is CA $497
CA $972 total
includes taxes & fees
Jul 8 - Jul 9
Spanish Queen @Venture Out, Cudjoe Key

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, (173 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
Direct Oceanfront-Atlantic Side-Dockage-Pool and 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, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is CA $335
CA $930 total
includes taxes & fees
Aug 3 - Aug 4
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is CA $1,272
CA $2,433 total
includes taxes & fees
Jul 8 - Jul 9
Seagate House by Brightwild Waterfront w Dock

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Cudjoe Key
9.6 out of 10, Exceptional, (53 reviews)
"Our stay was wonderful. Accommodations were as described and very comfortable. Location was great and the best views for the sunrise. "
United States
Kathy A.
The price is CA $559
CA $1,213 total
includes taxes & fees
Jul 19 - Jul 20
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

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)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is CA $330
CA $914 total
includes taxes & fees
Aug 2 - Aug 3
Charming 2-bedroom house with WiFi, AC in lovely 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)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is CA $288
CA $731 total
includes taxes & fees
Jul 12 - Jul 13
Kelly's Kabin - Adorable Private Summerland Key Cottage

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, (148 reviews)
"Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities. "
United States
Andy D.
The price is CA $671
CA $1,354 total
includes taxes & fees
Jul 8 - Jul 9
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

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
7.8 out of 10, Good, (20 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is CA $351
CA $731 total
includes taxes & fees
Jul 8 - Jul 9
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay! Prime location"
United States
Lacey C.
The price is CA $544
CA $1,284 total
includes taxes & fees
Jul 8 - Jul 9
Post Card Point #319 - Ocean Views!

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

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is CA $283
CA $709 total
includes taxes & fees
Jul 15 - Jul 16
SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Cudjoe Key
9.8 out of 10, Exceptional, (21 reviews)
"The view was stellar! "
United States
Dorothy H.
The price is CA $634
CA $1,398 total
includes taxes & fees
Jul 10 - Jul 11
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

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 CA $239
CA $804 total
includes taxes & fees
Jul 8 - Jul 9
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is CA $1,683
CA $2,895 total
includes taxes & fees
Jul 26 - Jul 27
Waterlane House by Brightwild Pool Boat Dock

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.
The price is CA $383
CA $846 total
includes taxes & fees
Jul 15 - Jul 16
Cudjoe Cottages, swimming pool, just 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

Sugarloaf Key Vacation Homes information

Number of reviews
929
Accommodation
895 Vacation Homes
Lowest Price
CA $709
Highest Price
CA $2,924

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