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612 Houses
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
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
$332
Price per night from
$332
Great rentals within 20 miles that match your search
Distance approx 16.77 km from Sugarloaf
Certificate of Excellence 
1/2 Block to Duval, World of its own -Nassau Suite
Florida Keys / Key West
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Swimming pool
- Car not necessary
- Air conditioning
Certificate of Excellence
Price per night from
$329
Price per night from
$329
Distance approx 16.87 km from Sugarloaf
Conch Haven Old Town 1/1 MONTHLY Rental
Florida Keys / Key West
1 4 30 nights min
- 1 bedroom
- sleeps 4
- 30 nights min
- Beach / lakeside relaxation
- Child Friendly
- Car not necessary
Price per night from
$96
Responds fast!
avg. 3 hours 4 minutes
Price per night from
$96
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
$339
Price per night from
$339
Distance approx 17 km from Sugarloaf
Casa Del Sol, a Key West Vacation (Truman Annex)
Florida Keys / Key West
2 6 7 nights min
- 2 bedrooms
- sleeps 6
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Price per night from
$236
Responds fast!
avg. 1 hour 8 minutes
Price per night from
$236
Distance approx 16.85 km from Sugarloaf
Casa Havana
Florida Keys / Key West
3 8 min stay varies
- 3 bedrooms
- sleeps 8
- min stay varies
- Child Friendly
- Air conditioning
- Private garden
Price per night from
$800
Price per night from
$800
Distance approx 12.88 km from Sugarloaf
Sunrise Drive
Florida Keys / Big Pine Key
3 8 min stay varies
- 3 bedrooms
- sleeps 8
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 8 mi
- Suitable for children age 5+
Price per night from
$204
Responds fast!
avg. 3 hours 4 minutes
Price per night from
$204
Distance approx 10.46 km from Sugarloaf
Charming Elevated Waterfront Home
Florida Keys / Big Pine Key
1 4 30 nights min
- 1 bedroom
- sleeps 4
- 30 nights min
- Child Friendly
- Air conditioning
- Ask about pets
Price per night from
$167
Responds fast!
avg. 3 hours 2 minutes
Price per night from
$167
Distance approx 11.43 km from Sugarloaf
Fisherman's Paradise in the Heart of Big Pine Key
Florida Keys / Big Pine Key
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Child Friendly
Price per night from
$117
Responds fast!
avg. 2 hours 20 minutes
Price per night from
$117
Distance approx 16.38 km from Sugarloaf
Coconut Beach
Florida Keys / Key West
1 4 7 nights min
- 1 bedroom
- sleeps 4
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Price per night from
$270
Responds fast!
avg. 3 hours 11 minutes
Price per night from
$270
Distance approx 11.44 km from Sugarloaf
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
Florida Keys / Big Pine Key
3 8 28 nights min
- 3 bedrooms
- sleeps 8
- 28 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$177
Price per night from
$177
Distance approx 4.06 km from Sugarloaf Show on Map
Oksana's Tropical Beach Oasis
Florida Keys / Cudjoe Key
4 14 7 nights min
- 4 bedrooms
- sleeps 14
- 7 nights min
- Nearest beach 10 mi
- Swimming pool
- Child Friendly
Map
Price per night from
$617
Price per night from
$617
Distance approx 16.24 km from Sugarloaf
"Little Paradise" Historic Seaport Old Town Key West
Florida Keys / Key West
2 4 7 nights min
- 2 bedrooms
- sleeps 4
- 7 nights min
- Child Friendly
- Air conditioning
- Private garden
Price per night from
$505
Responds fast!
avg. 2 hours 56 minutes
Price per night from
$505
Distance approx 15.02 km from Sugarloaf
Key West Gulf front Home with private dock and pool.
Florida Keys / Key West
3 6 28 nights min
- 3 bedrooms
- sleeps 6
- 28 nights min
- Nearest beach 2 mi
- Swimming pool
- Child Friendly
Price per night from
$336
Responds fast!
avg. 3 hours 57 minutes
Price per night from
$336
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
$797
Price per night from
$797
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
$899
Price per night from
$899
Distance approx 16.48 km from Sugarloaf
Classic Key West Estate ~ Weekly Rental
Florida Keys / Key West
7 14 min stay varies
- 7 bedrooms
- sleeps 14
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$1,542
Price per night from
$1,542
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
$505
Price per night from
$505
Distance approx 16.61 km from Sugarloaf
Key West Dreamin' ~ Weekly Rental
Florida Keys / Key West
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$565
Price per night from
$565
Distance approx 12.14 km from Sugarloaf
Key West Harbour Oceanfront Suites #2
Florida Keys / Key West
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$308
Price per night from
$308
Distance approx 12.13 km from Sugarloaf
Key West Harbour Oceanfront Suites #3
Florida Keys / Key West
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$308
Price per night from
$308
Distance approx 17 km from Sugarloaf
3 BIKES, Truman Annex w/2 PATIOS, A POOL, WIFI, & PARKING
Florida Keys / Key West
2 4 7 nights min
- 2 bedrooms
- sleeps 4
- 7 nights min
- Nearest beach 0.2 mi
- Swimming pool
- Child Friendly
Price per night from
$202
Responds fast!
avg. 57 minutes
Price per night from
$202
Distance approx 17.09 km from Sugarloaf
Truman Treasure
Florida Keys / Key West
3 5 7 nights min
- 3 bedrooms
- sleeps 5
- 7 nights min
- Nearest beach 0.49 mi
- Swimming pool
- Child Friendly
Price per night from
$573
Price per night from
$573
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
- Child Friendly
- Car not necessary
Price per night from
$2,518
Price per night from
$2,518
Distance approx 16.92 km from Sugarloaf
Just Off Duval 3 Bedroom Private Home with Pool
Florida Keys / Key West
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$392
Responds fast!
avg. 46 minutes
Price per night from
$392
Distance approx 15.42 km from Sugarloaf
3 Bedroom Oceanfront Condo Key West
Florida Keys / Key West
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Price per night from
$471
Responds fast!
avg. 46 minutes
Price per night from
$471
Distance approx 16.39 km from Sugarloaf
Cabana Boheme ~ Monthly Rental
Florida Keys / Key West
3 6 30 nights min
- 3 bedrooms
- sleeps 6
- 30 nights min
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$136
Price per night from
$136
Distance approx 9.13 km from Sugarloaf
Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys
Florida Keys / Ramrod Key
2 6 30 nights min
- 2 bedrooms
- sleeps 6
- 30 nights min
- Child Friendly
- Air conditioning
- Private garden
Price per night from
$138
Price per night from
$138
Distance approx 11.87 km from Sugarloaf
Caribbean Cove
Florida Keys / Big Pine Key
2 9 28 nights min
- 2 bedrooms
- sleeps 9
- 28 nights min
- Child Friendly
- Air conditioning
- Private garden
Price per night from
$102
Responds fast!
avg. 3 hours 17 minutes
Price per night from
$102
Distance approx 16.4 km from Sugarloaf
Old Town *Pink Conch House" with Pool
Florida Keys / Key West
4 8 30 nights min
- 4 bedrooms
- sleeps 8
- 30 nights min
- Child Friendly
Price per night from
$294
Price per night from
$294
Distance approx 16.54 km from Sugarloaf
Hidden Story-Book Cottage ~ Monthly Rental
Florida Keys / Key West
1 2 30 nights min
- 1 bedroom
- sleeps 2
- 30 nights min
- Ask about children
- Air conditioning
- Private garden
Price per night from
$113
Price per night from
$113
Distance approx 16.47 km from Sugarloaf
key west tree house
Florida Keys / Key West
1 3 30 nights min
- 1 bedroom
- sleeps 3
- 30 nights min
- Nearest beach 1 mi
- Child Friendly
- Car not necessary
Price per night from
$197
Price per night from
$197
Distance approx 16.93 km from Sugarloaf
HISTORIC KEY WEST - Turtle House - Sleeps 6
Florida Keys / Key West
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Nearest beach 0.8 mi
- Swimming pool
- Child Friendly
Price per night from
$587
Price per night from
$587
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
$494
Price per night from
$494
Distance approx 16.82 km from Sugarloaf
The Green House - Garden
Florida Keys / Key West
1 4 3 nights min
- 1 bedroom
- sleeps 4
- 3 nights min
- Child Friendly
Price per night from
$313
Price per night from
$313
Distance approx 16.73 km from Sugarloaf
Harbor Walk Hideaways
Florida Keys / Key West
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
Price per night from
$925
Price per night from
$925
Distance approx 17.05 km from Sugarloaf
Best Old Town Location in Key West
Florida Keys / Key West
2 6 7 nights min
- 2 bedrooms
- sleeps 6
- 7 nights min
- Swimming pool
- Child Friendly
- Car not necessary
Price per night from
$264
Price per night from
$264
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.