Vacation Rentals in Sugarloaf Shores, FL: Compare 10+ Sites & Save

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  5.  Sugarloaf Key
  6.  Sugarloaf Shores

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392 Best Vacation Rentals in Sugarloaf Shores (Starting from $191)

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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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

3 Bedrooms8 Guests
New to Booking
$191
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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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

$308
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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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

$297
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: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Dining & Pet Friendly!
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Dining & Pet Friendly!
House
Sugarloaf Key, FL, 33042, United States
0.4k from Sugarloaf Shores center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$383
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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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

$712
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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Waterfront Sugarloaf Key Home
Waterfront Sugarloaf Key Home
House
Upper Sugarloaf Key, FL, 33042, United States
0.5k from Sugarloaf Shores center

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

2 Bedrooms6 Guests
New to Booking
$277
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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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

$231
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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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

$641
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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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

$384
Average price / night
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Coral Queen Palm
Coral Queen Palm
House
Key West, FL, USA
3.9k from Sugarloaf Shores center

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

3 Bedrooms6 Guests
New to Booking
$330
Average price / night
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Sugarloaf Sunrise
Sugarloaf Sunrise
House
Summerland Key, FL, 33042, United States
0.6k from Sugarloaf Shores center

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

3 Bedrooms6 Guests
New to Booking
$374
Average price / night
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Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages
House
Summerland Key, FL, USA
4.3k from Sugarloaf Shores center

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

20 Bedrooms12 Guests
9.0

Fabulous

314 reviews

$458
Average price / night
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**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
House
Sugarloaf Key, FL, 33042, United States
0.7k from Sugarloaf Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$638
Average price / night
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Swimming Pool / Boat Dock / Close to Key West
Swimming Pool / Boat Dock / Close to Key West
House
Sugarloaf, FL, 33042, United States
0.8k from Sugarloaf Shores center

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

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
Check Availability
Serene 3-bedroom oceanfront house and dock in Sugarloaf Key
Serene 3-bedroom oceanfront house and dock in Sugarloaf Key
House
Summerland Key, FL, 33042, United States
0.8k from Sugarloaf Shores center

AC, Dryer, Heater, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
New to Booking
$308
Average price / night
Check Availability
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
House
Summerland Key, FL, 33042, United States
0.9k from Sugarloaf Shores center

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

4 Bedrooms8 Guests
New to Booking
$1035
Average price / night
Check Availability
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
House
Sugarloaf Key, FL, 33042, United States
0.9k from Sugarloaf Shores center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$552
Average price / night
Check Availability
Bayside Beauty, 3 bedroom with pool
Bayside Beauty, 3 bedroom with pool
House
Summerland Key, FL, 33042, United States
1.0k from Sugarloaf Shores center

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

3 Bedrooms8 Guests
New to Booking
$521
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals 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

You can explore 392 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 $191 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, 45 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 Balcony/Terrace, Laundry, 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.