Owner Direct Vacation Rentals in Sugarloaf Beach

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. ODVR
  2. Vacation Rentals
  3.  USA

  4.  Florida
  5.  Sugarloaf Key
  6.  Sugarloaf Beach

Refine your search

Price per night

Amenity Filter

Rating

293 Sugarloaf Beach Vacation Homes From $241

Looking for the ideal vacation rental in Sugarloaf Beach? 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.

Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
0.1k from Sugarloaf Beach center

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

2 Bedrooms4 Guests
New to Booking
$1395
Average price / night
Check Availability
Beach Front - Cassie`s Paradise Key West
Beach Front - Cassie`s Paradise Key West
House
Key West, FL, 33040, United States
0.2k from Sugarloaf Beach center

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

4 Bedrooms8 Guests
New to Booking
$6416
Average price / night
Check Availability
Bungalows Beach Key West - Hemingway
Bungalows Beach Key West - Hemingway
House
FL, USA
0.1k from Sugarloaf Beach center

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

2 Bedrooms6 Guests
New to Booking
$1104
Average price / night
Check Availability
The Hemingway - Beach Houses Key West
The Hemingway - Beach Houses Key West
House
Upper Sugarloaf Key, FL, 33042, United States
0.2k from Sugarloaf Beach center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
9.6

Exceptional

8 reviews

$1704
Average price / night
Check Availability
Bungalows Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
0.2k from Sugarloaf Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1695
Average price / night
Check Availability
Private and Exclusive Beach Getaway
Private and Exclusive Beach Getaway
House
Sugarloaf Key, FL, 33042, United States
0.2k from Sugarloaf Beach center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
8.0

Good

2 reviews

$2213
Average price / night
Check Availability
Palms Resort Main House - Key West
Palms Resort Main House - Key West
House
Sugarloaf Shores, FL, USA
0.4k from Sugarloaf Beach center

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

1 Bedroom12 Guests
New to Booking
$1248
Average price / night
Check Availability
The Lighthouse - Beach Houses Key West
The Lighthouse - Beach Houses Key West
House
Upper Sugarloaf Key, FL, 33042, United States
0.2k from Sugarloaf Beach center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
9.6

Exceptional

11 reviews

$1575
Average price / night
Check Availability
Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
0.4k from Sugarloaf Beach center

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

1 Bedroom8 Guests
New to Booking
$1198
Average price / night
Check Availability
Private and Exclusive Florida Keys Getaway
Private and Exclusive Florida Keys Getaway
House
Upper Sugarloaf Key, FL, 33042, United States
0.2k from Sugarloaf Beach center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms4 Guests
10.0

Exceptional

15 reviews

$1018
Average price / night
Check Availability
Coral Queen Palm
Coral Queen Palm
House
Key West, FL, USA
3.7k from Sugarloaf Beach center

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

3 Bedrooms6 Guests
New to Booking
$330
Average price / night
Check Availability
Waterfront Key West Oasis with Float Dock!
Waterfront Key West Oasis with Float Dock!
House
Key West, FL, USA
3.8k from Sugarloaf Beach center

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

3 Bedrooms8 Guests
New to Booking
$241
Average price / night
Check Availability
Beach Getaway in the Florida Keys
Beach Getaway in the Florida Keys
House
SUGARLOAF KEY, FL, 33042, United States
0.4k from Sugarloaf Beach center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms8 Guests
8.4

Very Good

7 reviews

$1055
Average price / night
Check Availability
Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
4.2k from Sugarloaf Beach center

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

13 Bedrooms10 Guests
7.4

Good

552 reviews

$313
Average price / night
Check Availability
Florida Keys Beach Getaway
Florida Keys Beach Getaway
House
Sugarloaf Key, FL, 33042, United States
0.4k from Sugarloaf Beach center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

5 Bedrooms12 Guests
9.8

Exceptional

28 reviews

$2038
Average price / night
Check Availability
Villa of the Setting Sun
Villa of the Setting Sun
House
Sugarloaf Beach, Sugarloaf Key, Florida, USA
6.2k from Sugarloaf Beach center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$2804
Average price / night
Check Availability
Ocean Acres: 3BR Oceanfront Estate on 20 Acres w/ Heated/Chilled Pool & Dog-Friendly
Ocean Acres: 3BR Oceanfront Estate on 20 Acres w/ Heated/Chilled Pool & Dog-Friendly
House
Sugarloaf Key, FL, 33042, United States
1.2k from Sugarloaf Beach center

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

3 Bedrooms8 Guests
New to Booking
$472
Average price / night
Check Availability
SUGARLOAF OASIS - heated pool & boat dock
SUGARLOAF OASIS - heated pool & boat dock
House
Sugarloaf Key, FL, 33042, United States
2.4k from Sugarloaf Beach center

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

1 Bedroom8 Guests
New to Booking
$410
Average price / night
Check Availability
JULY 11th on NOW AVAILABLE.   Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront
JULY 11th on NOW AVAILABLE. Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
House
Sugarloaf Key, FL, 33042, United States
2.4k from Sugarloaf Beach center

3 Bedrooms10 Guests
9.8

Exceptional

57 reviews

$660
Average price / night
Check Availability
Sunset Views • Heated Pool • Fire Pit • Sleeps 6
Sunset Views • Heated Pool • Fire Pit • Sleeps 6
House
Sugarloaf Key, FL, 33042, United States
2.5k from Sugarloaf Beach center

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

2 Bedrooms6 Guests
New to Booking
$524
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
2.6k from Sugarloaf Beach center

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

4 Bedrooms8 Guests
New to Booking
$1134
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 Beach.

Sugarloaf Beach Vacation Rentals on the Map

Why Travelers Love Using Owner Direct to
Find Austin Vacation Rentals

What makes our vacation rentals stand out?

check-mark

Verified Properties

Every vacation rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

check-mark

Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

check-mark

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 Beach. If you plan on staying in the Sugarloaf Beach 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 Beach

You can explore 293 verified vacation rentals in Sugarloaf Beach. 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 Beach 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 Beach 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 Beach welcome pets. Currently, 48 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 Beach often include amenities such as Balcony/Terrace, View, and Ocean View. 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.