Owner Direct Vacation Rentals in Sugarloaf Shores

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  5.  Sugarloaf Key
  6.  Sugarloaf Shores

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404 Sugarloaf Shores Vacation Homes From $241

Looking for the ideal vacation rental in Sugarloaf Shores? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
1.3k from Sugarloaf Shores center

Accommodations, Pools, Parking, Lodges, Cabins, Lodgings, Places to stay, Accessible hotels

13 Bedrooms10 Guests
7.4

Good

552 reviews

$313
Average price / night
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Blue Wahoo-Perfect Keys Getaway
Blue Wahoo-Perfect Keys Getaway
House
Sugarloaf Shores, FL, 33042, United States
0.1k from Sugarloaf Shores center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$494
Average price / night
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Palms Resort Main House - Key West
Palms Resort Main House - Key West
House
Sugarloaf Shores, FL, USA
2.9k from Sugarloaf Shores center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

1 Bedroom12 Guests
New to Booking
$1248
Average price / night
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**THE COMMODORE’S REFUGE @ SUGARLOAF KEY** Pool & Pickleball + LAST KEY SERVICES
**THE COMMODORE’S REFUGE @ SUGARLOAF KEY** Pool & Pickleball + LAST KEY SERVICES
House
Sugarloaf Key, FL, 33042, United States
0.2k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave

4 Bedrooms10 Guests
New to Booking
$425
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
2.9k from Sugarloaf Shores center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom8 Guests
New to Booking
$1198
Average price / night
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Our Happy Place
Our Happy Place
House
Upper Sugarloaf Key, FL, 33042, United States
0.3k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Laundry, Microwave, No Smoking

4 Bedrooms10 Guests
New to Booking
$273
Average price / night
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Bungalows Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
3.0k from Sugarloaf Shores center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1695
Average price / night
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Green Turtle Oasis: 4BR Canal Front Home, Pool, Dockage, Outdoor Dining & Pets
Green Turtle Oasis: 4BR Canal Front Home, Pool, Dockage, Outdoor Dining & Pets
House
Sugarloaf Key, FL, 33042, United States
0.3k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
New to Booking
$384
Average price / night
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Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
3.1k from Sugarloaf Shores center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$1395
Average price / night
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Waterfront Pool Home w/ 100' Dock, Tiki Hut & Boating Access Near Key West
Waterfront Pool Home w/ 100' Dock, Tiki Hut & Boating Access Near Key West
House
Sugarloaf Key, FL, 33042, United States
0.3k from Sugarloaf Shores center

AC, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
New to Booking
$544
Average price / night
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Bungalows Beach Key West - Hemingway
Bungalows Beach Key West - Hemingway
House
FL, USA
3.1k from Sugarloaf Shores center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$1104
Average price / night
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Stunning Sugarloaf, 3 bed house on huge plot to accomodate your RV or boat.
Stunning Sugarloaf, 3 bed house on huge plot to accomodate your RV or boat.
House
Summerland Key, FL, 33042, United States
0.3k from Sugarloaf Shores center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$338
Average price / night
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Villa of the Setting Sun
Villa of the Setting Sun
House
Sugarloaf Shores, Sugarloaf Key, Florida, USA
3.2k from Sugarloaf Shores center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

4 Bedrooms8 Guests
8.0

Good

1 reviews

$2804
Average price / night
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2-bedroom bungalow in charming Sugarloaf Key with dock, close to Key West
2-bedroom bungalow in charming Sugarloaf Key with dock, close to Key West
House
Summerland Key, FL, 33042, United States
0.4k from Sugarloaf Shores center

AC, Dryer, Internet, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$304
Average price / night
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Pelico Paradise
Pelico Paradise
House
Sugarloaf Shores, Sugarloaf Key, Florida, USA
3.5k from Sugarloaf Shores center

Parking, Pet Friendly, Air Conditioner, Internet, Child Friendly

5 Bedrooms10 Guests
9.6

Exceptional

2 reviews

$304
Average price / night
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Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
House
SugarLoaf, FL, 33042, United States
0.4k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

5 Bedrooms12 Guests
9.6

Exceptional

8 reviews

$321
Average price / night
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Waterfront Key West Oasis with Float Dock!
Waterfront Key West Oasis with Float Dock!
House
Key West, FL, USA
3.8k from Sugarloaf Shores center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$241
Average price / night
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Sugarloaf Key Home With Beach, Dock and Canal!
Sugarloaf Key Home With Beach, Dock and Canal!
House
Sugarloaf Key, FL, 33042, United States
0.5k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

26 reviews

$886
Average price / night
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Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite Community.
Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite Community.
House
Summerland Key, FL, 33042, United States
0.5k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$253
Average price / night
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Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
House
Sugarloaf, FL, 33042, United States
0.6k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

4 Bedrooms10 Guests
9.8

Exceptional

14 reviews

$536
Average price / night
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PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
House
Summerland Key, FL, 33042, United States
0.6k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$349
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Sugarloaf Shores.

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Frequently Asked Questions

There are a lot of options in Sugarloaf Shores. If you plan on staying in the Sugarloaf Shores area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Sugarloaf Shores

You can explore 404 verified vacation rentals in Sugarloaf Shores. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Sugarloaf Shores vary depending on the season, property size, and location. Rates typically start from around $241 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Sugarloaf Shores include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Sugarloaf Shores welcome pets. Currently, 46 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Sugarloaf Shores often include amenities such as View, Balcony/Terrace, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.