Owner Direct Beach Rentals in Sugarloaf Key

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  3.  USA

  4.  Florida

  5.  Sugarloaf Key

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266 Sugarloaf Key Beach Rentals From $156

Ready for a sun-soaked trip to Sugarloaf Key? Explore our index of beach house rentals and sunny coastal apartments. Owner Direct helps you filter through verified seaside options to find your next relaxing shore retreat.

Villa of the Setting Sun
Villa of the Setting Sun
House
Sugarloaf Key, Florida, USA
1.8k from Sugarloaf Key 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 Key Home With Beach, Dock and Canal!
Sugarloaf Key Home With Beach, Dock and Canal!
House
Sugarloaf Key, FL, 33042, United States
1.1k from Sugarloaf Key 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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Palms Resort Main House - Key West
Palms Resort Main House - Key West
House
Sugarloaf Shores, FL, USA
4.1k from Sugarloaf Key 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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**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
1.2k from Sugarloaf Key center

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

4 Bedrooms8 Guests
New to Booking
$491
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
4.1k from Sugarloaf Key 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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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
1.3k from Sugarloaf Key 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 Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
4.2k from Sugarloaf Key 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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**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
1.3k from Sugarloaf Key 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 Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
4.3k from Sugarloaf Key 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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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
1.3k from Sugarloaf Key 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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Newly built home in Cudjoe Key
Newly built home in Cudjoe Key
House
Cudjoe Key, FL, USA
4.5k from Sugarloaf Key center

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

3 Bedrooms7 Guests
New to Booking
$583
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
1.4k from Sugarloaf Key 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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Tranquility in Paradise - Cudjoe
Tranquility in Paradise - Cudjoe
House
Summerland Key, FL, USA
4.7k from Sugarloaf Key center

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

3 Bedrooms8 Guests
New to Booking
$156
Average price / night
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Blue Wahoo-Perfect Keys Getaway
Blue Wahoo-Perfect Keys Getaway
House
Sugarloaf Shores, FL, 33042, United States
1.4k from Sugarloaf Key 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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Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
5.1k from Sugarloaf Key center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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Amazing Waterfront Home with Fabulous Pool and Sunset Views
Amazing Waterfront Home with Fabulous Pool and Sunset Views
House
Sugarloaf, FL, 33042, United States
1.7k from Sugarloaf Key center

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

3 Bedrooms9 Guests
10.0

Exceptional

1 reviews

$504
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
1.8k from Sugarloaf Key center

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

4 Bedrooms8 Guests
New to Booking
$615
Average price / night
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Sublimely private luxury home with enveloping oceanfront views near Key West
Sublimely private luxury home with enveloping oceanfront views near Key West
House
Sugarloaf Key, FL, 33042, United States
1.8k from Sugarloaf Key center

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

4 Bedrooms8 Guests
9.4

Superb

47 reviews

$2671
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
1.8k from Sugarloaf Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$349
Average price / night
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Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and Sunsets
Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and Sunsets
House
Sugarloaf, FL, 33042, United States
1.8k from Sugarloaf Key center

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

4 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$629
Average price / night
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Open Water Views, Sunsets and 2 New Beautiful Pools Create Your Island Oasis
Open Water Views, Sunsets and 2 New Beautiful Pools Create Your Island Oasis
House
Sugarloaf, FL, 33042, United States
1.9k from Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave

7 Bedrooms17 Guests
New to Booking
$1086
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 Beach Rentals in Sugarloaf Key.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

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

You can explore 266 verified beach rentals in Sugarloaf Key. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Sugarloaf Key vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $156 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Sugarloaf Key offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Sugarloaf Key welcome pets. Currently, 44 listings allow pets, although policies may vary by property. It's also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it's recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Sugarloaf Key often include amenities designed for coastal living, such as Ocean View, View, and Balcony/Terrace. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It's best to review the amenities section of each listing to confirm what is included and plan accordingly.