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Holiday homes in Sugarloaf Shores You’ll Love

Top-Rated Sugarloaf Shores Holiday homes for Every Budget and Style!

Looking for a holiday home in Sugarloaf Shores (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $55.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Sugarloaf Shores.

We found 42 Holiday-homes in Sugarloaf Shores and the surrounding area (within 20 miles)

OCEANIA... water front cottage retreat ~ in Cudjoe Key, USA

OCEANIA... water front cottage retreat ~

Villa in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Drive
Providing a garden, OCEANIA...
  • Parking
  • Sauna
  • Family rooms
  • Outdoor pool
  • Kids' pool

Good 18 Reviews 7.7

from $313.58 Show details »

NAUTILUS...ocean front cottage retreat ~ in Cudjoe Key, USA

NAUTILUS...ocean front cottage retreat ~

Villa in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Drive
Providing a garden, NAUTILUS...ocean front cottage retreat ~ features accommodations in Cudjoe Key.
  • Parking
  • Family rooms
  • Outdoor pool
  • Kids' pool
  • Swimming pool

Superb 22 Reviews 9.3

from $322.44 Show details »

Bungalows Beach Key West Palm in Sugarloaf Shores, USA

Bungalows Beach Key West Palm

Holiday home in Sugarloaf Shores, Florida , 15620 Old State Road 4a
Bungalows Beach Key West Palm offers accommodations in Sugarloaf Shores, 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

Very good 1 Reviews 8.0

from $1.064.51 Show details »

Bungalows Sugarloaf Beach Key West - Hammock House in Sugarloaf Shores, USA

Bungalows Sugarloaf Beach Key West - Ham...

Holiday home in Sugarloaf Shores, Florida , 15680 Old State Road 4a
21 miles from Ernest Hemingway Home and Museum in Sugarloaf Shores, Bungalows Sugarloaf Beach Key West - Hammock House provides accommodations with ac...
  • Parking
  • Pets allowed
  • Bar
  • Fitness centre
  • Family rooms

Exceptional 1 Reviews 10.0

from $81.00 Show details »

Palms Resort Main House - Key West in Sugarloaf Shores, USA

Palms Resort Main House - Key West

Holiday home in Sugarloaf Shores, Florida , 15760 Old State Road 4a
Featuring a garden, Palms Resort Main House - Key West provides accommodations in Sugarloaf Shores.
  • Parking
  • Pets allowed

no reviews

from $1.645.02 Show details »

Palms Resort Beach Key West - Guest House in Key West, USA

Palms Resort Beach Key West - Guest Hous...

Holiday home in Key West near Sugarloaf Shores, Florida , 15760 Old State Road 4a
Offering a garden, Palms Resort Beach Key West - Guest House features accommodations in Key West.
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $72.00 Show details »

Bungalows Beach Key West - Azucar in Key West, USA

Bungalows Beach Key West - Azucar

Holiday home in Key West near Sugarloaf Shores, Florida , 15760 Old State Road 4a
Providing a garden, Bungalows Beach Key West - Azucar features accommodations in Key West.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $1.023.60 Show details »

Bay Harbor View in Bay Point, USA

Bay Harbor View

Holiday home in Bay Point near Sugarloaf Shores, Florida
Bay Harbor View is located in Bay Point, just 16 miles from Southernmost Point and 16 miles from Mallory Square.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $63.00 Show details »

Fish Camp in Sugarloaf Shores, USA

Fish Camp

Holiday home in Sugarloaf Shores, Florida
Fish Camp is located in Sugarloaf Shores, just 15 miles from Southernmost Point and 15 miles from Mallory Square.

no reviews

from $92.00 Show details »

Coral Queen Palm in Key West, USA

Coral Queen Palm

Holiday home in Key West near Sugarloaf Shores, Florida
Coral Queen Palm offers accommodations in Key West, 15 miles from Key West Aquarium and 15 miles from Mallory Dock.
  • Parking

no reviews

from $81.00 Show details »

Waterfront Key West Oasis with Float Dock! in Key West, USA

Waterfront Key West Oasis with Float Doc...

Holiday home in Key West near Sugarloaf Shores, Florida
Waterfront Key West Oasis with Float Dock! is located in Key West, just 15 miles from Ernest Hemingway Home and Museum and 15 miles from Duval Street.
  • Parking

no reviews

from $94.00 Show details »

Baypoint Oasis by Last Key Realty in Sugarloaf Shores, USA

Baypoint Oasis by Last Key Realty

Holiday home in Sugarloaf Shores, Florida , 16 Bay Drive
Baypoint Oasis by Last Key Realty is located in Sugarloaf Shores, just 15 miles from Ernest Hemingway Home and Museum and 15 miles from Duval Street.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $63.00 Show details »

Blue Horizon by Last Key Realty in Sugarloaf Shores, USA

Blue Horizon by Last Key Realty

Holiday home in Sugarloaf Shores, Florida , 17387 E Dolphin Street
Blue Horizon by Last Key Realty offers accommodations in Sugarloaf Shores, 18 miles from Ernest Hemingway Home and Museum and 18 miles from Duval Stre...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $72.00 Show details »

Casa La Sirena in Sugarloaf Shores, USA

Casa La Sirena

Holiday home in Sugarloaf Shores, Florida , 17159 Amberjack Lane
Casa La Sirena offers accommodations in Sugarloaf Shores, 18 miles from Ernest Hemingway Home and Museum and 18 miles from Duval Street.
  • Parking
  • Pets allowed
  • Swimming Pool

no reviews

from $77.00 Show details »

Tranquility in Paradise - Sugarloaf - 17 miles to Key West in Sugarloaf Shores, USA

Tranquility in Paradise - Sugarloaf - 17...

Holiday home in Sugarloaf Shores, Florida , 17084 Green Turtle Lane West
Providing water sports facilities, Tranquility in Paradise - Sugarloaf - 17 miles to Key West features accommodations in Sugarloaf Shores.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $99.00 Show details »

Sugarloaf Serenity in Sugarloaf Shores, USA

Sugarloaf Serenity

Holiday home in Sugarloaf Shores, Florida
Sugarloaf Serenity is located in Sugarloaf Shores, just 17 miles from Southernmost Point and 18 miles from Mallory Square.

no reviews

from $72.00 Show details »

Kingfish Cove in Summerland Key, USA

Kingfish Cove

Holiday home in Summerland Key near Sugarloaf Shores, Florida , 17194 Kingfish Lane West
Providing a garden, Kingfish Cove offers accommodations in Summerland Key.
  • Parking
  • Pets allowed
  • Family rooms
  • Swimming Pool

no reviews

from $65.00 Show details »

Parrotfish Pointe in Cudjoe Key, USA

Parrotfish Pointe

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida
Parrotfish Pointe is located in Cudjoe Key, just 24 miles from Ernest Hemingway Home and Museum and 24 miles from Duval Street.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $59.00 Show details »

The Mermaid Manor in Cudjoe Key, USA

The Mermaid Manor

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida
The Mermaid Manor offers accommodations in Cudjoe Key, 24 miles from Ernest Hemingway Home and Museum and 24 miles from Duval Street.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $90.00 Show details »

Hawkins Lookout in Cudjoe Key, USA

Hawkins Lookout

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida
Hawkins Lookout is located in Cudjoe Key, just 24 miles from Ernest Hemingway Home and Museum and 24 miles from Duval Street.
  • Parking
  • Pets allowed

no reviews

from $73.00 Show details »

Tree Top Paradise in Cudjoe Key, USA

Tree Top Paradise

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Drive 179
23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Tree Top Paradise provides accommodations with access to a spa center.
  • Parking
  • Pets allowed
  • Family rooms
  • Spa and wellness centre
  • Outdoor pool

Fabulous 50 Reviews 8.7

from $154.58 Show details »

Carefree on Cudjoe by Last Key Realty in Cudjoe Key, USA

Carefree on Cudjoe by Last Key Realty

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 22927 Drake Lane
Carefree on Cudjoe by Last Key Realty is located in Cudjoe Key, just 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $59.00 Show details »

Mermaid Magic by Last Key Realty in Cudjoe Key, USA

Mermaid Magic by Last Key Realty

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Drive #320
Mermaid Magic by Last Key Realty offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street.
  • Parking
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $449.65 Show details »

Dock Holiday in Cudjoe Key, USA

Dock Holiday

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida
Dock Holiday offers accommodations in Cudjoe Key, 23 miles from Duval Street and 23 miles from Southernmost Point.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 6 Reviews 7.1

from $351.48 Show details »

Island Oasis ~ YOUR Paradise Awaits! in Cudjoe Key, USA

Island Oasis ~ YOUR Paradise Awaits!

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Drive
Island Oasis ~ YOUR Paradise Awaits! offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Stree...
  • Parking
  • Outdoor pool
  • Kids' pool
  • Swimming pool
  • Swimming Pool

Very good 4 Reviews 8.0

from $256.59 Show details »

Number of Holiday homes in Sugarloaf Shores 42
Number of guest ratings 417
Average price per night $93.00
Lowest price per night $55,00
Highest price per night $489,91

Top 10 Cheapest Holiday-homes in Sugarloaf Shores

Discover the Cheapest Holiday-homes in Sugarloaf Shores – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Sugarloaf Shores

Check out the Most Booked Holiday-homes in Sugarloaf Shores – Based on Guest Popularity.

Holiday homes in Sugarloaf Shores (Florida), comfortable and familiar

Staying in a holiday or vacation home in Sugarloaf Shores can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Sugarloaf Shores for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Sugarloaf Shores should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com