Vacation Rentals & House Rentals in Sugarloaf

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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Fireplace
Private tennis court
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Clothes dryer
Table tennis
Pool or snooker table
Games room
Private outdoor pool (heated)
Private outdoor pool (unheated)
Shared indoor pool
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Fax machine
Swing set or jungle gym
Video player
Stove
Solarium or roof terrace
TV
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
Fridge
Boat available
Freezer
Microwave
Linen provided
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Children - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

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31 Houses

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Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and

Sugarloaf house

4 bedrooms
4 bathrooms

sleeps 10

Responds fast! avg. 2 hours 34 minutes

Match: Boat available

All filters match

Price per night from

$458

Great rentals within 20 miles that match your search

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

Match: Boat available

All filters match

Price per night from

$1,949

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

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$912

80' luxury yacht

Stock Island house

3 bedrooms
4 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$4,015

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

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

Match: Boat available

All filters match

Price per night from

$700

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

All filters match

Price per night from

$287

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$525

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

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

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

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

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

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$859

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

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Boat available

All filters match

Price per night from

$478

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

All filters match

Price per night from

$1,717

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

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

$973

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

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

All filters match

Price per night from

$859

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Boat available

All filters match

Price per night from

$744

Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024

Key West apartment

2 bedrooms
1 bathroom

sleeps 4

Match: Boat available

All filters match

Price per night from

$382

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

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 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

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$510

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$444

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

Match: Boat available

All filters match

Price per night from

$144

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

Match: Boat available

All filters match

Price per night from

$174

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 Sunset Harbor

Stock Island condo

1 bedroom
1 bathroom

sleeps 4

Match: Boat available

All filters match

Price per night from

$523

Hyatt Sunset Harbor

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Boat available

All filters match

Price per night from

$525

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Sugarloaf Rentals

Per night

31 Houses

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and

NEW LISTING! 40’ Luxury Catamaran Yacht!

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

80' luxury yacht

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

Luxury Oceanview Pool Eco-friendly Villa Near Key West

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

Hyatt Windward Pointe

Walk to Duval and Mallory Square!

Walk to Duval and Mallory Square!

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

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

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

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

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

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

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

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

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

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024

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

Walk to Duval and Mallory Square!

Hyatt Beach House! Quiet Key West Location!

Hyatt Windward Pointe

Hyatt Windward Pointe

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Coconut Mallory Resort and Marina

Hyatt Sunset Harbor

Hyatt Sunset Harbor

Viewing 31 of 31
rentals in Sugarloaf

Also consider

Sugarloaf Rentals

Per night

31 Houses

Viewing 31 of 31rentals in Sugarloaf

Also consider

Viewing 31 of 31
rentals in Sugarloaf