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The 10 Best Cottages in Islamorada, USA

Check out our selection of great cottages in Islamorada

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Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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Featuring air-conditioned accommodation with a pool with a view, garden view and a patio, Anglers Reef Getaway is set in Islamorada. This beachfront property offers access to a balcony, squash on the squash court, free private parking and free WiFi. The property is non-smoking and is situated 600 metres from Windley Key.

loved the location and the quick responses from the host.

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9
Wonderful
24 reviews

Anglers Reef Paradise is located in Islamorada, 300 metres from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

This air-conditioned holiday home has 2 bedrooms and 2.5 bathrooms, a cable flat-screen TV, and a fully equipped kitchen. The holiday home also provides a bathroom with a shower.

It was very clean and confortable; and the facilities where great, we enjoyed our time at the beach and used the canoes and paddle board! Great time

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9.2
Wonderful
26 reviews

Set in Islamorada, less than 1 km from Windley Key and 5 km from Upper Matecumbe Key, Peaceful Palms A2 offers air-conditioned accommodation with a terrace and free WiFi. With sea views, this accommodation features a balcony. The accommodation provides a 24-hour front desk and parking on-site.

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Price from
$342.17
per night

Located 2.2 km from Anne's Beach, 13 km from Upper Matecumbe Key and 18 km from Windley Key, West Plaza Del Lago offers accommodation situated in Islamorada. Among the facilities at this property are a 24-hour front desk and an ATM, along with free WiFi throughout the property. The property is non-smoking and is set 1 km from Sea Oats Beach.

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Villa Riolo is situated in Islamorada, 9.2 km from Upper Matecumbe Key, 14 km from Windley Key, and 30 km from Pigeon Key. Both free WiFi and parking on-site are available at the holiday home free of charge. The property is non-smoking and is located 2.5 km from Sea Oats Beach.

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Price from
$252.22
per night

Sunshine Place is a beachfront property set in Islamorada, 1.4 km from Windley Key and 4.2 km from Upper Matecumbe Key. Among the facilities at this property are a 24-hour front desk and an ATM, along with free WiFi throughout the property. The property is non-smoking and is situated 17 km from Pigeon Key.

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Boasting a spa bath, Sandglass 4 is set in Islamorada. Among the facilities at this property are a 24-hour front desk and an ATM, along with free WiFi throughout the property. The property is non-smoking and is situated a few steps from Sea Oats Beach.

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Price from
$640.15
per night

Offering sea views, Pelican Landing is an accommodation situated in Islamorada, 1.1 km from Sea Oats Beach and 2.2 km from Anne's Beach. Among the facilities at this property are a 24-hour front desk and an ATM, along with free WiFi throughout the property. The property is non-smoking and is set 13 km from Upper Matecumbe Key.

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Price from
$549.25
per night

Featuring sea views, Palms 417 offers accommodation with a balcony, around 3.3 km from Upper Matecumbe Key. This beachfront property offers access to a terrace. The holiday home features parking on-site, a fitness room and a 24-hour front desk.

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Palms 407 is a beachfront property located in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key. Among the facilities at this property are a 24-hour front desk and a lift, along with free WiFi throughout the property. The property is non-smoking and is set 24 km from Pigeon Key.

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Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.
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Most booked cottages in Islamorada this month

Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 24 reviews

    Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

    The amenities,the location, the villas and the pool

  • Anglers Reef Paradise
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 26 reviews

    Anglers Reef Paradise is located in Islamorada, 984 feet from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

    perfektes Südstaatenfeeling sehr exquisit und sicher

  • Peaceful Palms A2

    Peaceful Palms A2 is a recently renovated vacation home in Islamorada, near Windley Key. This vacation home features air-conditioned accommodations with a terrace.

  • West Plaza Del Lago

    West Plaza Del Lago offers accommodations in Islamorada, a 12-minute walk from Sea Oats Beach and 1.3 miles from Anne's Beach.

  • Villa Riolo
    Breakfast options

    Villa Riolo is located in Islamorada, just 1.6 miles from Sea Oats Beach and 5.7 miles from Upper Matecumbe Key. Both free Wifi and parking on-site are available at the vacation home free of charge.

  • Sunshine Place
    Breakfast options

    Sunshine Place offers accommodations in Islamorada, a 17-minute walk from Windley Key and 2.6 miles from Upper Matecumbe Key.

  • Sandglass 4
    Breakfast options

    Sandglass 4 is located in Islamorada, just a few steps from Sea Oats Beach and 1.4 miles from Anne's Beach.

  • Pelican Landing
    Breakfast options

    Pelican Landing is located in Islamorada, just a 12-minute walk from Sea Oats Beach and 1.4 miles from Anne's Beach.

These cottages in Islamorada have options with FREE cancellation

  • Palms 417
    Free cancellation options available

    Palms 417 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key. This beachfront property offers access to a terrace.

  • Palms 407
    Free cancellation options available

    Palms 407 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 404
    Free cancellation options available

    Palms 404 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 317
    Free cancellation options available

    Palms 317 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 314
    Free cancellation options available

    Palms 314 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 313
    Free cancellation options available

    Palms 313 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 309
    Free cancellation options available

    Palms 309 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 301
    Free cancellation options available

    Palms 301 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

Traveling by car? These cottages in Islamorada offer free parking!

  • Ocean Harbour K31

    Ocean Harbour K31 is located in Islamorada, just 2.7 miles from Windley Key and 6 miles from Upper Matecumbe Key.

  • Martin Family Fish Camp

    Martin Family Fish Camp offers accommodations in Islamorada, a 7-minute walk from Upper Matecumbe Key and 3 miles from Windley Key.

  • Lyons Landing

    Lyons Landing offers accommodations in Islamorada, 1.6 miles from Windley Key and 4.8 miles from Upper Matecumbe Key.

  • Little Bay Cottage

    Little Bay Cottage offers accommodations in Islamorada, 2.7 miles from Windley Key and 13 miles from Pigeon Key. The air-conditioned accommodation is a 13-minute walk from Upper Matecumbe Key.

  • Little Bay Compound

    Just a 13-minute walk from Upper Matecumbe Key and 0.6 miles from History of Diving Museum, Little Bay Compound features accommodations in Islamorada with a garden.

  • Harbor House

    Harbor House is located in Islamorada, just 1.4 miles from Windley Key and 4.7 miles from Upper Matecumbe Key.

  • Blue Water Retreat

    Blue Water Retreat offers accommodations in Islamorada, 1.3 miles from Sea Oats Beach and 5.9 miles from Upper Matecumbe Key. This beachfront property offers access to a balcony.

  • Beacon Reef 503

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 503 features accommodations in Islamorada with a garden.

Cottages That Guests Love in Islamorada

  • Avg. price/night: $387
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 831 reviews
    Ideally located , we had a beachfront “cozy” cottage… lovely view from our table and chairs on the porch and from the 2 lounge chairs right outside our door.. our cottage kitchen was well equipped and the bed comfortable. Plentiful towels and coffee maker with coffee packets.
    Karen
    Young couple
  • Avg. price/night: $387
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 831 reviews
    This property is absolutely gorgeous, the cottage was clean and comfortable. The staff could not have been kinder and more helpful. We will definitely be back and would recommend to anyone wanting a quiet Keys experience.
    Jenny
    Young couple
  • Avg. price/night: $468.23
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 1,524 reviews
    So much right there, beach, 2 pools, eat/drink, hot tub, and much more! Also close to lots of restaurants and shops. Our room was amazing and spacious. All of the employees were super friendly and helpful.
    Michele
    Family with young children
  • Avg. price/night: $231.63
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 1,059 reviews
    We had a cute cabin in a great location. Hotel had free coffee and a nice pool.
    Elaine
    Young couple
  • Avg. price/night: $387
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 831 reviews
    Extremely clean! We stayed in a cottage and had everything that we would need to stay for a extended time, unfortunately we were only there for one night, the cottage was booked for the rest of the week and all other rooms were also booked for the week. I would definitely go back.
    Linda
    Young couple
  • Avg. price/night: $387
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 831 reviews
    Cottages on the beach loved that
    margaret
    Young couple
  • Avg. price/night: $468.23
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 1,524 reviews
    Great installation, charming personal. Cozy room and decoration We will come back for sure!
    Ana
    Family with young children
  • 8.0
    Scored 8.0
    Very Good
    Rated very good
     · 1,218 reviews
    The property we originally booked was under repair so they gave us a lovely cottage over looking the docks.
    nicola
    Young couple
  • Avg. price/night: $387
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 831 reviews
    Love the area, cottage/ bungalow. Staff was SO Nice, Daniell at Check in in was beyond helpful, including during the wk. Lev an Chris the bartenders are great an friendly, Chris also took us fishing
    Kelly
    Group
  • Avg. price/night: $231.63
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 1,059 reviews
    The beds were soft. The bungalow reminded me of a Beach cottage/shore house.
    S.
    Young couple