Vacation Rentals & House Rentals in Sugarloaf Key

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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Cot available
Sauna
High chair
Sea view
Safe
Dishwasher
Children's pool
Clothes dryer
Cribs
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Table tennis
Ceiling Fans
Games room
Trampoline
Pool or snooker table
Towels provided
Hair dryer
Stove
Fridge
Freezer
Microwave
Linen provided
Bicycles available
Fax machine
Climbing frame
Swing set or jungle gym
Private fishing lake or river
Staffed property
Boat available
Video player
Housekeeping Included

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Pets allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Elevator access
Wheelchair accessible

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Beach or lakeside relaxation
Tennis in town
Water sports
Fishing

Cycling trips
Golf course on site or within 15 min walk
Waterfront
Golf within 30mins drive

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27 house rentals

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NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

Match: Boat available

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Price per night from

$1,946

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Key West apartment

1 bedroom
1 bathroom

sleeps 4

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

Match: Boat available

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Price per night from

$287

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Boat available

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Price per night from

$745

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

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Price per night from

$1,374

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

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Price per night from

$859

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

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Price per night from

$859

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

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Price per night from

$911

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$859

Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024

Key West apartment

2 bedrooms
1 bathroom

sleeps 4

Match: Boat available

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Price per night from

$382

Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Boat available

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Price per night from

$478

High Tide awaits your next visit upgraded condo close to Smathers Beach

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$859

Our Nautical Home in Key West is available for amazing prices Summer of 2023

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$859

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Key West apartment

3 bedrooms
2 bathrooms

sleeps 8

Match: Boat available

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Price per night from

$1,718

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$974

Poolside Breeze a Tropical Retreat has a wrap around Balcony best location

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$859

80' luxury yacht

Stock Island house

3 bedrooms
4 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$4,008

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$622

Hyatt Sunset Harbor

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

1 bedroom
1 bathroom

sleeps 4

Match: Boat available

All filters match

Price per night from

$523

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$445

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$525

Coconut Mallory Resort and Marina

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$346

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$471

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$654

All-Inclusive Yacht Margarita Flaca: Marina OR Anchor on the Ocean: Free Charter

Stock Island yacht

1 bedroom
1 bathroom

sleeps 6

Match: Boat available

All filters match

Price per night from

$263

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$667

Also consider

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Vacation Rentals & House Rentals in Sugarloaf Key

Per night

27 house rentals

NEW LISTING! 40’ Luxury Catamaran Yacht!

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024

Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.

High Tide awaits your next visit upgraded condo close to Smathers Beach

Our Nautical Home in Key West is available for amazing prices Summer of 2023

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Poolside Breeze a Tropical Retreat has a wrap around Balcony best location

80' luxury yacht

Walk to Duval and Mallory Square!

Hyatt Sunset Harbor

Hyatt Windward Pointe

Hyatt Sunset Harbor

Hyatt Windward Pointe

Hyatt Windward Pointe

Coconut Mallory Resort and Marina

Hyatt Beach House! Quiet Key West Location!

Walk to Duval and Mallory Square!

All-Inclusive Yacht Margarita Flaca: Marina OR Anchor on the Ocean: Free Charter

Walk to Duval and Mallory Square!

Viewing 27 of 27
rentals in Sugarloaf Key

Also consider

Vacation Rentals & House Rentals in Sugarloaf Key

Per night

27 house rentals

Viewing 27 of 27rentals in Sugarloaf Key

Also consider

Viewing 27 of 27
rentals in Sugarloaf Key