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Holiday homes in Sugarloaf Shores You’ll Love (Page 2)

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)

Pelicans Roost, Waterfront comfort at Venture Out in Cudjoe Key, USA

Pelicans Roost, Waterfront comfort at Ve...

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Drive Unit 454
Featuring free bikes, Pelicans Roost, Waterfront comfort at Venture Out provides accommodations in Cudjoe Key.
  • Parking
  • Family rooms
  • Outdoor pool
  • Kids' outdoor play equipment
  • Kids' pool

Fabulous 23 Reviews 8.9

from $310.32 Show details »

Blue Skies in Summerland Key, USA

Blue Skies

Holiday home in Summerland Key near Sugarloaf Shores, Florida
Blue Skies offers accommodations in Summerland Key, 21 miles from Southernmost Point and 22 miles from Mallory Square.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $70.00 Show details »

Turtle Cove Views by Last Key Realty in Cudjoe Key, USA

Turtle Cove Views by Last Key Realty

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Dr #524
Turtle Cove Views 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

Very good 2 Reviews 8.5

from $447.30 Show details »

Newly built home in Cudjoe Key in Cudjoe Key, USA

Newly built home in Cudjoe Key

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 430 Pattison Drive
Newly built home in Cudjoe Key is located in Cudjoe Key, just 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street.
  • Parking
  • Family rooms
  • Outdoor pool
  • Kids' outdoor play equipment
  • Swimming pool

no reviews

from $87.00 Show details »

Tidewater Views by Last Key Realty in Cudjoe Key, USA

Tidewater Views by Last Key Realty

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 701 Spanish Main Dr #594
Tidewater Views by Last Key Realty offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $425.10 Show details »

Sun Outdoors Sugarloaf Key in Summerland Key, USA

Sun Outdoors Sugarloaf Key

Holiday home in Summerland Key near Sugarloaf Shores, Florida , 3000 Johnson Road
Sun Outdoors Sugarloaf Key provides air-conditioned accommodations in Summerland Key.
  • Parking
  • Pets allowed
  • Bar
  • Swimming Pool

Superb 559 Reviews 9.1

from $127.35 Show details »

The Blue Marlin in Cudjoe Key, USA

The Blue Marlin

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida
The Blue Marlin is located in Cudjoe Key, just 23 miles from Key West Aquarium and 23 miles from Mallory Dock.
  • Parking
  • Pets allowed

no reviews

from $84.00 Show details »

Paradise Found in Key West, USA

Paradise Found

Holiday home in Key West near Sugarloaf Shores, Florida
Paradise Found is located in Key West, just 23 miles from Southernmost Point and 23 miles from Mallory Square.

no reviews

from $84.00 Show details »

Blackbeard`s Hideaway in Key West, USA

Blackbeard`s Hideaway

Holiday home in Key West near Sugarloaf Shores, Florida
Blackbeard`s Hideaway is located in Key West, just 23 miles from Duval Street and 23 miles from Southernmost Point.

no reviews

from $92.00 Show details »

Tranquility in Paradise - Cudjoe in Summerland Key, USA

Tranquility in Paradise - Cudjoe

Holiday home in Summerland Key near Sugarloaf Shores, Florida , 21069 5th Avenue
Tranquility in Paradise - Cudjoe is located in Summerland Key, just 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 1 Reviews 10.0

from $87.00 Show details »

Villa of the Setting Sun in Pirates Cove, USA

Villa of the Setting Sun

Holiday home in Pirates Cove near Sugarloaf Shores, Florida
Villa of the Setting Sun offers accommodations in Pirates Cove, 20 miles from Ernest Hemingway Home and Museum and 20 miles from Duval Street.
  • Parking
  • Sauna
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 1 Reviews 8.0

from $2.392.88 Show details »

Key Lime Time in Cudjoe Key, USA

Key Lime Time

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida
Offering pool views, Key Lime Time in Cudjoe Key provides accommodations and a garden.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $100.00 Show details »

El Paraiso in Summerland Key, USA

El Paraiso

Holiday home in Summerland Key near Sugarloaf Shores, Florida
El Paraiso offers accommodations in Summerland Key, 23 miles from Southernmost Point and 23 miles from Mallory Square.

no reviews

from $79.00 Show details »

Tarpon Canal in Key West, USA

Tarpon Canal

Holiday home in Key West near Sugarloaf Shores, Florida
Tarpon Canal offers accommodations in Key West, 21 miles from Southernmost Point and 21 miles from Mallory Square.

no reviews

from $92.00 Show details »

Keysie Does It by Last Key Realty in Cudjoe Key, USA

Keysie Does It by Last Key Realty

Holiday home in Cudjoe Key near Sugarloaf Shores, Florida , 21650 Overseas Highway #102
Keysie Does It by Last Key Realty offers accommodations in Cudjoe Key, 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $411.44 Show details »

Loggerhead Lagoon - Modern Waterfront Home in Pirates Cove, USA

Loggerhead Lagoon - Modern Waterfront Ho...

Holiday home in Pirates Cove near Sugarloaf Shores, Florida , 886 Loggerhead Lane
Loggerhead Lagoon - Modern Waterfront Home is located in Pirates Cove, just 20 miles from Ernest Hemingway Home and Museum and 20 miles from Duval Str...
  • Parking
  • Pets allowed

no reviews

from $53.00 Show details »

Sugarloaf Lodge in Sugarloaf Shores, USA

Sugarloaf Lodge

Lodge in Sugarloaf Shores, Florida , 17001 Overseas Highway
Located in Key West, Florida, this lodge features an outdoor pool and a tennis court.
  • Parking
  • Restaurant
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 415 Reviews 7.7

from $111.38 Show details »

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