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Holiday homes in Summerland Key You’ll Love

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

Looking for a holiday home in Summerland Key (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $63.00 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 Summerland Key.

We found 54 Holiday-homes in Summerland Key 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 Summerland Key, 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 Summerland Key, 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 »

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, 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 »

Parrotfish Pointe in Cudjoe Key, USA

Parrotfish Pointe

Holiday home in Cudjoe Key near Summerland Key, 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 Summerland Key, 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 Summerland Key, 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 Summerland Key, 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 »

Cayman Cottage in Summerland Key, USA

Cayman Cottage

Holiday home in Summerland 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 »

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

Carefree on Cudjoe by Last Key Realty

Holiday home in Cudjoe Key near Summerland Key, 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 »

Love Shack in Summerland Key, USA

Love Shack

Holiday home in Summerland 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 »

Mermaid Magic by Last Key Realty in Cudjoe Key, USA

Mermaid Magic by Last Key Realty

Holiday home in Cudjoe Key near Summerland Key, 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 Summerland Key, 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 Summerland Key, 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 »

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

Pelicans Roost, Waterfront comfort at Ve...

Holiday home in Cudjoe Key near Summerland Key, 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, 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 Summerland Key, 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 Summerland Key, 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 Summerland Key, 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 »

Skyway Living in Summerland Key, USA

Skyway Living

Holiday home in Summerland 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 »

Sun Outdoors Sugarloaf Key in Summerland Key, USA

Sun Outdoors Sugarloaf Key

Holiday home in Summerland Key, 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 »

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

Experience Coastal Living at its Best Fl...

Holiday home in Summerland 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 Summerland 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 near Summerland 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, 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 »

The Blue Marlin in Cudjoe Key, USA

The Blue Marlin

Holiday home in Cudjoe Key near Summerland Key, 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 »

Number of Holiday homes in Summerland Key 54
Number of guest ratings 1,240
Average price per night $289.00
Lowest price per night $63,00
Highest price per night $1.645,02

Top 10 Most Popular Holiday-homes in Summerland Key

Explore the Most Popular Holiday-homes in Summerland Key – Ranked by Average Guest Ratings.

Top 10 Cheapest Holiday-homes in Summerland Key

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

Top 10 Most Booked Holiday-homes in Summerland Key

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

Holiday homes in Summerland Key (Florida), comfortable and familiar

Staying in a holiday or vacation home in Summerland 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 Summerland 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 Summerland 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