Sugarloaf Vacation Rentals & Homes - 165 Rentals Available
165 Vacation rentals
Sugarloaf Sunset
Sugarloaf House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$167.00
from $167.00 / night
Bay Pointe
Sugarloaf House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$144.00
from $144.00 / night
Bow Channel Manor
Sugarloaf House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$189.00
from $189.00 / night
South Point Shores
Sugarloaf House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$170.00
from $170.00 / night
Your search has been expanded 16.8 miles to include more rentals
Mango House
Little Torch Key House - 11.4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$87.00
from $87.00 / night
Breezy Palms
Ramrod Key House - 9.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$140.00
from $140.00 / night
Make My Day
Cudjoe Key House - 3.5 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$150.00
from $150.00 / night
Tree House
Ramrod Key House - 9.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$104.00
from $104.00 / night
Bonefish Lodge
Key West House - 6.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 28 nights min
- Child friendly
$150.00
from $150.00 / night
Buccaneer Boathouse
Little Torch Key House - 10.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
$114.00
from $114.00 / night
Ramrod Retreat
Ramrod Key House - 9.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$97.00
from $97.00 / night
Blue Tranquility
Ramrod Key House - 9.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Child friendly
- Pet friendly
$167.00
from $167.00 / night
Palm Villa
Little Torch Key House - 10.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$191.00
from $191.00 / night
Island Time (both halves of duplex)
Big Pine Key House - 12.8 miles away
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$197.00
from $197.00 / night
Paradise Palms
Summerland Key House - 5.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Swimming pool
- Child friendly
- Air conditioning
$151.00
from $151.00 / night
Hideaway Bay
Big Pine Key House - 11.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 31 nights min
- Child friendly
- Air conditioning
- Pet friendly
$109.00
from $109.00 / night
Big Torch Retreat
Summerland Key House - 9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$100.00
from $100.00 / night
The Key's only real beach house Dock and pool
Key West House - 1.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$394.00
from $394.00 / night
Blue Lagoon
Summerland Key House - 6.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$200.00
from $200.00 / night
Casa Turquesa
Summerland Key House - 6.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$217.00
from $217.00 / night
Private beach estate. Gated, tropical peace and quiet. Dock.
Key West House - 1.2 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$465.00
from $465.00 / night
737 The Place, a Monthly Rental Old Town Key West
Key West Apartment - 16.5 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 30 nights min
- Beach/lakeside relaxation
- Nearest beach 0.5 mi
- Ask about children
$115.00
from $115.00 / night
2 bedroom Condo Presented Key West Style
Key West Apartment - 13.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Nearest beach 2 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 23 minutes
$180.00
from $180.00 / night
Pirate's Cove
Cudjoe Key House - 4.9 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$74.00
from $74.00 / night
Blue Marlin
Little Torch Key House - 10.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$132.00
from $132.00 / night
Coral House
Ramrod Key House - 9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$119.00
from $119.00 / night
Pink House
Cudjoe Key House - 3.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$167.00
from $167.00 / night
Key's only real beach home.Gated, private, dock,pool
Key West House - 1.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$536.00
from $536.00 / night
Sunset Bay (weekly rental)
Ramrod Key House - 8.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$272.00
from $272.00 / night
Mermaid's Rest
Cudjoe Key House - 4.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$134.00
from $134.00 / night
Caribbean Dream
Summerland Key House - 6.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$200.00
from $200.00 / night
Key West's only Real Beach House
Key West Guest house - 1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$393.00
from $393.00 / night
Duval Penthouse - private pool/parking with roof deck - A++ Location
Key West Penthouse - 16.8 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Nearest beach 1 mi
- Child friendly
- Car not necessary
$796.00
from $796.00 / night
Lost In Paradise
Big Pine Key House - 11.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$140.00
from $140.00 / night
Catch of the Day!
Cudjoe Key House - 5 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$110.00
from $110.00 / night
Gone Fishing
Summerland Key House - 6.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 28 nights min
- Swimming pool
- Child friendly
- Air conditioning
$211.00
from $211.00 / night
Paradise Bay
Cudjoe Key House - 4.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$107.00
from $107.00 / night
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