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698 Houses
Green Turtle Landing
Florida Keys / Sugarloaf
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Map
Price per night from
$139
Price per night from
$139
Canal-Front Paradise! Spacious 3BR w/ Private Pool, Boat Dock & Deck
Florida Keys / Sugarloaf
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$319
Price per night from
$319
Bay Pointe
Florida Keys / Sugarloaf
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Map
Price per night from
$139
Price per night from
$139
South Point Shores
Florida Keys / Sugarloaf
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Map
Price per night from
$160
Price per night from
$160
Bow Channel Manor
Florida Keys / Sugarloaf
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Map
Price per night from
$187
Price per night from
$187
Tranquility in Paradise - Sugarloaf Key (17 miles to Key West)
Florida Keys / Sugarloaf
5 9 28 nights min
- 5 bedrooms
- sleeps 9
- 28 nights min
- Child Friendly
- Pet Friendly
Map
Price per night from
$280
Price per night from
$280
Great rentals within 20 miles that match your search
Distance approx 12.28 km from Sugarloaf
Spectacular Atlantic Ocean View Condo (MONTHLY)
Florida Keys / Key West
2 6 28 nights min
- 2 bedrooms
- sleeps 6
- 28 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Price per night from
$134
Price per night from
$134
Distance approx 6.42 km from Sugarloaf
Shark Key Home with beach 10 Min from Duval St
Florida Keys / Key West
3 8 21 nights min
- 3 bedrooms
- sleeps 8
- 21 nights min
- Child Friendly
- Ask about pets
Price per night from
$289
Responds fast!
avg. 3 hours 15 minutes
Price per night from
$289
Distance approx 17.09 km from Sugarloaf
The Water's Edge
Florida Keys / Key West
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Price per night from
$837
Price per night from
$837
Distance approx 16.87 km from Sugarloaf
Heavenly Hideout at Rainbow's End ~ Weekly Rental
Florida Keys / Key West
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Ask about children
- Air conditioning
- Private garden
Price per night from
$745
Price per night from
$745
Distance approx 4.06 km from Sugarloaf Show on Map
Oksana's Tropical Beach Oasis
Florida Keys / Cudjoe Key
5 14 7 nights min
- 5 bedrooms
- sleeps 14
- 7 nights min
- Nearest beach 10 mi
- Swimming pool
- Child Friendly
Map
Price per night from
$592
Price per night from
$592
Distance approx 16.77 km from Sugarloaf
Key West Wabi Sabi ~ Weekly Rental
Florida Keys / Key West
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$745
Price per night from
$745
Distance approx 16.68 km from Sugarloaf
Villa Nouveau Key West ~ Weekly Rental
Florida Keys / Key West
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$839
Price per night from
$839
Distance approx 16.83 km from Sugarloaf
Old Town Eyebrow:Luxurious/Private Home
Florida Keys / Key West
3 8 30 nights min
- 3 bedrooms
- sleeps 8
- 30 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$424
Price per night from
$424
Distance approx 17 km from Sugarloaf
Garden Oasis at Truman Annex
Florida Keys / Key West
2 4 7 nights min
- 2 bedrooms
- sleeps 4
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$272
Price per night from
$272
Distance approx 16.63 km from Sugarloaf
Twice as Nice ~ Weekly Rental
Florida Keys / Key West
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$839
Price per night from
$839
Distance approx 17 km from Sugarloaf
Truman Annex 2 Bedroom 1 Bath
Florida Keys / Key West
2 4 7 nights min
- 2 bedrooms
- sleeps 4
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$303
Price per night from
$303
Distance approx 16.68 km from Sugarloaf
The Meeting Point - Key West ~ Weekly Rental
Florida Keys / Key West
11 24 min stay varies
- 11 bedrooms
- sleeps 24
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$2,418
Price per night from
$2,418
Distance approx 9.07 km from Sugarloaf
Bahia Azul
Florida Keys / Ramrod Key
4 8 30 nights min
- 4 bedrooms
- sleeps 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Price per night from
$227
Price per night from
$227
Distance approx 4.71 km from Sugarloaf
Mermaid's Rest
Florida Keys / Cudjoe Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Price per night from
$132
Price per night from
$132
Distance approx 16.84 km from Sugarloaf
Seaport Treasure Estate ~ Monthly Rental
Florida Keys / Key West
6 12 30 nights min
- 6 bedrooms
- sleeps 12
- 30 nights min
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$592
Price per night from
$592
Distance approx 10.47 km from Sugarloaf
Island Chalet
Lower Keys / Little Torch Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Price per night from
$116
Price per night from
$116
Distance approx 16.87 km from Sugarloaf
The Tree House Old Town 2 Bedroom MONTHLY Rental
Florida Keys / Key West
2 7 30 nights min
- 2 bedrooms
- sleeps 7
- 30 nights min
- Ask about children
- Car not necessary
- Air conditioning
Price per night from
$112
Price per night from
$112
Distance approx 5.01 km from Sugarloaf
Cudjoe Ocean Shores
Florida Keys / Cudjoe Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Price per night from
$96
Price per night from
$96
Distance approx 11.35 km from Sugarloaf
Mango House
Lower Keys / Little Torch Key
2 4 30 nights min
- 2 bedrooms
- sleeps 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Price per night from
$67
Price per night from
$67
Distance approx 4.87 km from Sugarloaf
Charming 3bedroom/2bath home in the Florida Keys
Florida Keys / Cudjoe Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Price per night from
$92
Price per night from
$92
Distance approx 6.33 km from Sugarloaf
Caribbean House
Lower Keys / Summerland Key
2 4 30 nights min
- 2 bedrooms
- sleeps 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Price per night from
$82
Price per night from
$82
Distance approx 4.86 km from Sugarloaf
Pirate's Cove
Florida Keys / Cudjoe Key
2 4 30 nights min
- 2 bedrooms
- sleeps 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Price per night from
$69
Price per night from
$69
Distance approx 13.2 km from Sugarloaf
Island Time 2 (half of duplex)
Florida Keys / Big Pine Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Price per night from
$92
Price per night from
$92
Distance approx 13.75 km from Sugarloaf
Elegant, Two Bedroom Condo Close to the Ocean
Florida Keys / Key West
2 6 3 nights min
- 2 bedrooms
- sleeps 6
- 3 nights min
- Nearest beach 2 mi
- Swimming pool
- Child Friendly
Price per night from
$258
Responds fast!
avg. 1 hour 34 minutes
Price per night from
$258
Distance approx 15.47 km from Sugarloaf
By The Beautiful Sea ~ A Key West Beach Front Condo ~ Weekly Rental
Florida Keys / Key West
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Beach / lakeside relaxation
- Swimming pool
- Ask about children
Price per night from
$474
Price per night from
$474
Distance approx 13.09 km from Sugarloaf
Atlantis
Florida Keys / Big Pine Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
Price per night from
$103
Price per night from
$103
Distance approx 11.63 km from Sugarloaf
Blue Heron
Florida Keys / Big Pine Key
2 4 30 nights min
- 2 bedrooms
- sleeps 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Price per night from
$85
Price per night from
$85
Distance approx 16.07 km from Sugarloaf
Vacation house for a family for oct
Florida Keys / Key West
3 5 6 nights min
- 3 bedrooms
- sleeps 5
- 6 nights min
- Child Friendly
Price per night from
$497
Price per night from
$497
Distance approx 13.75 km from Sugarloaf
Certificate of Excellence
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Florida Keys / Key West
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Certificate of Excellence
Price per night from
$197
Responds fast!
avg. 2 hours 58 minutes
Price per night from
$197
Distance approx 5.2 km from Sugarloaf
Paradise Palms
Lower Keys / Summerland Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$146
Price per night from
$146
Distance approx 1.03 km from Sugarloaf Show on Map
Key West's only Real Beach House
Florida Keys / Key West
2 4 7 nights min
- 2 bedrooms
- sleeps 4
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Ask about children
Map
Price per night from
$388
Price per night from
$388
Distance approx 4.82 km from Sugarloaf
Tropical Blue Adventure Waterfront at Venture Out
Florida Keys / Cudjoe Key
2 6 3 nights min
- 2 bedrooms
- sleeps 6
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 30 mi
- Swimming pool
Price per night from
$173
Price per night from
$173
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.