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Holiday homes in Big Pine Key You’ll Love

Top-Rated Big Pine Key Holiday homes for Every Budget and Style!

Looking for a holiday home in Big Pine Key (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $53.00 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 Big Pine Key.

We found 37 Holiday-homes in Big Pine Key and the surrounding area (within 20 miles)

Ocean View Room Barnacle bed and breakfast Deers Beach Front Suite in Big Pine Key, USA

Ocean View Room Barnacle bed and breakfa...

Holiday home in Big Pine Key, Florida , 1557 Long Beach Drive
Ocean View Room Barnacle bed and breakfast Deers Beach Front Suite is located in Big Pine Key, just 22 miles from Florida Keys Aquarium Encounters and...
  • Parking
  • Pets allowed

no reviews

from $63.00 Show details »

Ocean Depth Room Barnacle bed and breakfast Deers Suite in Big Pine Key, USA

Ocean Depth Room Barnacle bed and breakf...

Holiday home in Big Pine Key, Florida , 1557 Long Beach Drive
Ocean Depth Room Barnacle bed and breakfast Deers Suite is located in Big Pine Key, just 22 miles from Florida Keys Aquarium Encounters and 12 miles f...
  • Parking
  • Pets allowed

no reviews

from $65.00 Show details »

Star Room Barnacle Bed And Breakfast in Big Pine Key, USA

Star Room Barnacle Bed And Breakfast

Holiday home in Big Pine Key, Florida , 1557 Long Beach Drive
Star Room Barnacle Bed And Breakfast is located in Big Pine Key, just 22 miles from Florida Keys Aquarium Encounters and 12 miles from Seven Mile Brid...
  • Parking
  • Pets allowed

no reviews

from $376.80 Show details »

Salty Slumber Relaxing 2 bedroom 2 bath Get Away in the Lower Keys in Summerland Key, USA

Salty Slumber Relaxing 2 bedroom 2 bath...

Holiday home in Summerland Key near Big Pine Key, Florida , 1323 Hudgins Drive
26 miles from Ernest Hemingway Home and Museum in Summerland Key, Salty Slumber Relaxing 2 bedroom 2 bath Get Away in the Lower Keys provides accommod...
  • Parking
  • Pets allowed
  • Sauna
  • Family rooms

no reviews

from $70.00 Show details »

Cayman Cottage in Summerland Key, USA

Cayman Cottage

Holiday home in Summerland Key near Big Pine Key, Florida
Cayman Cottage offers accommodations in Summerland Key, 28 miles from Duval Street and 28 miles from Southernmost Point.

no reviews

from $81.00 Show details »

Love Shack in Summerland Key, USA

Love Shack

Holiday home in Summerland Key near Big Pine Key, Florida
Love Shack offers accommodations in Summerland Key, 26 miles from Southernmost Point and 26 miles from Mallory Square.

no reviews

from $60.00 Show details »

Skyway Living in Summerland Key, USA

Skyway Living

Holiday home in Summerland Key near Big Pine Key, Florida
Skyway Living offers accommodations in Summerland Key, 25 miles from Ernest Hemingway Home and Museum and 25 miles from Duval Street.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $63.00 Show details »

Experience Coastal Living at its Best Florida Keys in Summerland Key, USA

Experience Coastal Living at its Best Fl...

Holiday home in Summerland Key near Big Pine Key, Florida
Experience Coastal Living at its Best Florida Keys offers accommodations in Summerland Key, 26 miles from Florida Keys Aquarium Encounters and 27 mile...
  • Parking

no reviews

from $91.00 Show details »

L`archipel in Key West, USA

L`archipel

Holiday home in Key West near Big Pine Key, Florida
L`archipel is located in Key West, just 27 miles from Duval Street and 28 miles from Southernmost Point.

no reviews

from $81.00 Show details »

Sunset Retreat in Big Pine Key, USA

Sunset Retreat

Holiday home in Big Pine Key, Florida
Sunset Retreat is located in Big Pine Key, just 31 miles from Duval Street and 31 miles from Southernmost Point.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $60.00 Show details »

Summerland Canal in Summerland Key, USA

Summerland Canal

Holiday home in Summerland Key near Big Pine Key, Florida
Summerland Canal is located in Summerland Key, just 25 miles from Ernest Hemingway Home and Museum and 25 miles from Duval Street.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $67.00 Show details »

Beachside Fantasy in Big Pine Key, USA

Beachside Fantasy

Holiday home in Big Pine Key, Florida
Beachside Fantasy is located in Big Pine Key, just 23 miles from Florida Keys Aquarium Encounters and 30 miles from Ernest Hemingway Home and Museum.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $91.00 Show details »

Manatee Watch in Big Pine Key, USA

Manatee Watch

Holiday home in Big Pine Key, Florida
Manatee Watch is located in Big Pine Key, just 30 miles from Duval Street and 30 miles from Southernmost Point.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $82.00 Show details »

Fishermen`s Paradise in Big Pine Key, USA

Fishermen`s Paradise

Holiday home in Big Pine Key, Florida
Fishermen`s Paradise offers accommodations in Big Pine Key, 12 miles from Seven Mile Bridge and 22 miles from Captain Hook s Marina Dive Center.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 1 Reviews 9.0

from $1.161.22 Show details »

Waterfront Beach House with Dock & Heated Pool in Summerland Key, USA

Waterfront Beach House with Dock & Heate...

Holiday home in Summerland Key near Big Pine Key, Florida , 263 Barry Avenue
Waterfront Beach House with Dock & Heated Pool offers accommodations in Summerland Key, 25 miles from Florida Keys Aquarium Encounters and 28 miles fr...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming Pool

no reviews

from $85.00 Show details »

Waterfront Cozy Cottage with Boat Ramp & Dock in Little Torch Key, USA

Waterfront Cozy Cottage with Boat Ramp &...

Holiday home in Little Torch Key near Big Pine Key, Florida , 363 Barry Avenue
Waterfront Cozy Cottage with Boat Ramp & Dock is located in Little Torch Key, just 29 miles from Ernest Hemingway Home and Museum and 29 miles from Du...
  • Parking
  • Pets allowed

Very good 1 Reviews 8.0

from $84.00 Show details »

Waterfront Anchor House with Boat Basin & Ramp in Summerland Key, USA

Waterfront Anchor House with Boat Basin...

Holiday home in Summerland Key near Big Pine Key, Florida , 373 Barry Avenue
Waterfront Anchor House with Boat Basin & Ramp is located in Summerland Key, just 29 miles from Ernest Hemingway Home and Museum and 29 miles from Duv...
  • Parking
  • Pets allowed

Exceptional 2 Reviews 9.5

from $87.00 Show details »

Waterfront Haven House with Boat Basin & Ramp in Summerland Key, USA

Waterfront Haven House with Boat Basin &...

Holiday home in Summerland Key near Big Pine Key, Florida , 371 Barry Avenue
Waterfront Haven House with Boat Basin & Ramp offers accommodations in Summerland Key, 29 miles from Ernest Hemingway Home and Museum and 29 miles fro...
  • Parking
  • Pets allowed

Fabulous 5 Reviews 9.0

from $89.00 Show details »

Waterfront Captain House with Boat Basin & Ramp in Summerland Key, USA

Waterfront Captain House with Boat Basin...

Holiday home in Summerland Key near Big Pine Key, Florida , 383 Barry Avenue
Waterfront Captain House with Boat Basin & Ramp offers accommodations in Summerland Key, 29 miles from Ernest Hemingway Home and Museum and 29 miles f...
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $81.00 Show details »

Sea-Esta in Big Pine Key, USA

Sea-Esta

Holiday home in Big Pine Key, Florida
Sea-Esta is located in Big Pine Key, just 30 miles from Duval Street and 30 miles from Southernmost Point.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $64.00 Show details »

The Nautical Nimbus in Big Pine Key, USA

The Nautical Nimbus

Holiday home in Big Pine Key, Florida
The Nautical Nimbus offers accommodations in Big Pine Key, 30 miles from Ernest Hemingway Home and Museum and 30 miles from Duval Street.
  • Parking

no reviews

from $93.00 Show details »

Go Fish Inn in Big Pine Key, USA

Go Fish Inn

Holiday home in Big Pine Key, Florida , 31041 Hollerich Dr.
Go Fish Inn is located in Big Pine Key, just 23 miles from Florida Keys Aquarium Encounters and 13 miles from Seven Mile Bridge.

no reviews

from $96.00 Show details »

Tarpon Tales in Big Pine Key, USA

Tarpon Tales

Holiday home in Big Pine Key, Florida
Tarpon Tales offers accommodations in Big Pine Key, 23 miles from Captain Hook s Marina Dive Center and 24 miles from A Deep Blue Dive Center.

no reviews

from $95.00 Show details »

Salty Air Retreat in Little Torch Key, USA

Salty Air Retreat

Holiday home in Little Torch Key near Big Pine Key, Florida
Salty Air Retreat offers accommodations in Little Torch Key, 29 miles from Ernest Hemingway Home and Museum and 29 miles from Duval Street.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $69.00 Show details »

Foster`s Folly in Key West, USA

Foster`s Folly

Holiday home in Key West near Big Pine Key, Florida
Foster`s Folly is located in Key West, just 30 miles from Duval Street and 30 miles from Southernmost Point.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $79.00 Show details »

Number of Holiday homes in Big Pine Key 37
Number of guest ratings 943
Average price per night $271.00
Lowest price per night $53,00
Highest price per night $2.392,88

Top 10 Cheapest Holiday-homes in Big Pine Key

Discover the Cheapest Holiday-homes in Big Pine Key – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Big Pine Key

Check out the Most Booked Holiday-homes in Big Pine Key – Based on Guest Popularity.

Holiday homes in Big Pine Key (Florida), comfortable and familiar

Staying in a holiday or vacation home in Big Pine Key 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 Big Pine Key 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 Big Pine Key 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