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Properties in Upper Sugarloaf Key, Sugarloaf Key, Florida, United States of America. March 2, 2021 through March 2, 2021

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  1. Sugar Loaf Lodge

    2.57 mi from Upper Sugarloaf Key
    3.8 out of 5 Good (808 reviews)
    We have 8 left at
    Price was $299Price is now $249
    per night
    $280 total
    Includes taxes & fees
    More information about Sugar Loaf Lodge, Opens in a new window
  2. Looe Key Reef Resort

    7.55 mi from Upper Sugarloaf Key
    Free Cancellation
    3.5 out of 5 Good (636 reviews)
    We have 7 left at
    Price is $154
    per night
    $173 total
    Includes taxes & fees
    More information about Looe Key Reef Resort, Opens in a new window
  3. Parmer's Resort

    8.78 mi from Upper Sugarloaf Key
    Breakfast included
    4.2 out of 5 Very Good (997 reviews)
    We have 1 left at
    Price is $245
    per night
    $276 total
    Includes taxes & fees
    More information about Parmer's Resort, Opens in a new window
  4. 3 Bedroom Beach House Close TO Beach & KEY West

    Entire home
    3 bedrooms, 2 bathrooms
    11.75 mi from Upper Sugarloaf Key
    4.2 out of 5 Very Good (11 reviews)
    Price was $425Price is now $415
    per night
    $720 total
    Includes taxes & fees
    More information about 3 Bedroom Beach House Close TO Beach & KEY West, Opens in a new window
  5. Large, Dog-friendly Home on Three Secluded Acres W/ Balconies, Deck, & Views

    Entire home
    5 bedrooms, 4 bathrooms
    0.6 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.3 out of 5 Excellent (33 reviews)
    We are sold out
    More information about Large, Dog-friendly Home on Three Secluded Acres W/ Balconies, Deck, & Views, Opens in a new window
  6. Extensive Keys House w/ Bikes, Private Pool, Free Wifi, & In-home Washer/dryers

    Entire home
    8 bedrooms, 7 bathrooms
    0.65 mi from Upper Sugarloaf Key
    May 23 - May 24
    5.0 out of 5 Exceptional (1 review)
    We are sold out
    More information about Extensive Keys House w/ Bikes, Private Pool, Free Wifi, & In-home Washer/dryers, Opens in a new window
  7. Pet Friendly Amazing Location in Paradise

    Entire home
    3 bedrooms, 2 bathrooms
    1.12 mi from Upper Sugarloaf Key
    May 23 - May 24
    5.0 out of 5 Exceptional (3 reviews)
    We are sold out
    More information about Pet Friendly Amazing Location in Paradise, Opens in a new window
  8. Cudjoe Key 3bdr,2 Bath Pool, 20 min From Key West, Ocean Access, Bikes, Canoe

    Entire home
    3 bedrooms, 2 bathrooms
    1.25 mi from Upper Sugarloaf Key
    May 23 - May 24
    5.0 out of 5 Exceptional (9 reviews)
    We are sold out
    More information about Cudjoe Key 3bdr,2 Bath Pool, 20 min From Key West, Ocean Access, Bikes, Canoe, Opens in a new window
  9. Oceanside, pet Friendly, Smart Home With Plenty of Paddle Equipment

    Entire home
    3 bedrooms, 2 bathrooms
    1.42 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.7 out of 5 Exceptional (13 reviews)
    We are sold out
    More information about Oceanside, pet Friendly, Smart Home With Plenty of Paddle Equipment, Opens in a new window
  10. Bring Your Boat

    Entire home
    2 bedrooms, 2 bathrooms
    1.39 mi from Upper Sugarloaf Key
    May 23 - May 24
    5.0 out of 5 Exceptional (1 review)
    We are sold out
    More information about Bring Your Boat, Opens in a new window
  11. White Vacation Home, Read our Reviews. Private Dock, Private Heated Pool

    Entire home
    4 bedrooms, 4 bathrooms
    1.76 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.9 out of 5 Exceptional (114 reviews)
    We are sold out
    More information about White Vacation Home, Read our Reviews. Private Dock, Private Heated Pool, Opens in a new window
  12. Yellow Vacation Home. Weekly, Private Heated Pool

    Entire home
    3 bedrooms, 2 bathrooms
    1.76 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.9 out of 5 Exceptional (81 reviews)
    We are sold out
    More information about Yellow Vacation Home. Weekly, Private Heated Pool, Opens in a new window
  13. Blue Vacation Home. Boat Dock, Private Heated Pool, View Over the Atlantic Ocean

    Entire home
    4 bedrooms, 2 bathrooms
    1.77 mi from Upper Sugarloaf Key
    May 23 - May 24
    5.0 out of 5 Exceptional (75 reviews)
    We are sold out
    More information about Blue Vacation Home. Boat Dock, Private Heated Pool, View Over the Atlantic Ocean, Opens in a new window
  14. Oceanfront Home-swimming Pool-boat Ramp-dockage-just 20 Miles From Key West

    Entire home
    3 bedrooms, 2 bathrooms
    1.84 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.4 out of 5 Excellent (10 reviews)
    We are sold out
    More information about Oceanfront Home-swimming Pool-boat Ramp-dockage-just 20 Miles From Key West, Opens in a new window
  15. Luxury Home #107-pool,dock,kayaks,bikes,on Ocean Near Key West,free Trailer Keep

    Entire home
    2 bedrooms, 3 bathrooms
    2.02 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.8 out of 5 Exceptional (89 reviews)
    We are sold out
    More information about Luxury Home #107-pool,dock,kayaks,bikes,on Ocean Near Key West,free Trailer Keep, Opens in a new window
  16. Gated Community on Open Water With Dock, Heated Pool, Kayaks, Bikes

    Entire home
    2 bedrooms, 3 bathrooms
    2.02 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.9 out of 5 Exceptional (120 reviews)
    We are sold out
    More information about Gated Community on Open Water With Dock, Heated Pool, Kayaks, Bikes, Opens in a new window
  17. Luxury Home #111-pool,dock,kayaks,bikes,on Ocean Near Key West,free Trailer Keep

    Entire home
    2 bedrooms, 3 bathrooms
    2.02 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.9 out of 5 Exceptional (74 reviews)
    We are sold out
    More information about Luxury Home #111-pool,dock,kayaks,bikes,on Ocean Near Key West,free Trailer Keep, Opens in a new window
  18. Luxury Home #109-pool,dock,kayaks,bikes,on Ocean Near Key West,free Trailer Keep

    Entire home
    2 bedrooms, 3 bathrooms
    2.02 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.9 out of 5 Exceptional (90 reviews)
    We are sold out
    More information about Luxury Home #109-pool,dock,kayaks,bikes,on Ocean Near Key West,free Trailer Keep, Opens in a new window
  19. Private Home in the Keys -pool-bikes-kayaks Special Pricing Save!

    Entire home
    2 bedrooms, 3 bathrooms
    2.03 mi from Upper Sugarloaf Key
    May 23 - May 24
    4.9 out of 5 Exceptional (41 reviews)
    We are sold out
    More information about Private Home in the Keys -pool-bikes-kayaks Special Pricing Save!, Opens in a new window
  20. Charming Artist Home - Canal Front - Deep Water 40 Dock!

    Entire home
    3 bedrooms, 3 bathrooms
    2.02 mi from Upper Sugarloaf Key
    May 23 - May 24
    5.0 out of 5 Exceptional (3 reviews)
    We are sold out
    More information about Charming Artist Home - Canal Front - Deep Water 40 Dock!, Opens in a new window